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When John Twells sent up the Bat-Signal to do this ‘best backpacker records’ list, we assembled a cracker jack squad of late ’90s and early ’00s underground rap heads and at first it all seemed straightforward. We all had a pretty solid idea of what ‘backpacker’ entails, but when it came time to actually make the list we faced an amorphous and very loosely defined pool of candidates. Major label releases were nixed right off the bat (ironically, this eliminated a few items that were canonical for underground fans at the time.) We then had to decide what actually constitutes backpacker rap – do abstract lyrical miracles take precedence over intelligent thugs? Do instrumental albums count? Where are the cut-off dates? Do we put precedence on certain labels and locales over others? What about records that were popular and significant at the time but didn’t age well? And so on.

After some strong, and frankly still ongoing arguments, we realized there is no single definitive guideline to follow. With five contributors, all of a similar age and with similar passion for rap, we each experienced the ‘backpacker’ phenomenon from different locales and perspectives. Albums and songs significant to some meant nothing to others, and matters of personal taste on what even constitutes good rap music sometimes varied wildly. So we tried to concoct a panoramic overview which is rooted in our common interests but also represents the diversity of our opinions and the passion driving our individual points of view.

In the end, I think we managed to do it all justice and cover the most pertinent ground. Naturally our readers may, and likely will, disagree – and we are okay with that. In fact, we welcome it. If a conversation about rap doesn’t turn into a heated argument, it’s probably not a very interesting conversation. Enjoy. – Alex Piyevksy

This list was compiled by Steady Bloggin’s Alex Piyevsky, Purple Tape Pedigree founder and ex-Atoms Family member Geng, FACT’s John Twells, FACT and Passion of the Weiss’ Son Raw, and the mysterious Jeff Rascobeamer, with cantankerous assistance from Skinny Friedman.

Read this next: The 100 Greatest IDM Tracks

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100. Various Artists
Music for the Advancement of Hip Hop
(Anticon, 1999)

Love ’em or hate ’em, you can’t talk about indie hip-hop without giving a nod to West Coast weirdos Anticon. The label was established in 1998 by divisive rapper Sole and a number of fellow emcees and producers, and over the course of the next decade offered an intriguing foil to rest of the country’s worthy, self-conscious output.

Music for the Advancement of Hip Hop was a statement of intent and showed off the label’s key operatives. Sole, Buck 65, Them, Deep Puddle Dynamics and more offer up tracks, and while the nasal rapping and zany production still alienates many rap fans, they undoubtably carved out their own niche. Their influence can still be spotted now.

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99. Mixmaster Mike
Anti-Theft Device
(Asphodel, 1998)

If we’re talking hip-hop, it’s important to acknowledge that the genre encompasses more than rap, and while turntablism has fallen out of favor in recent years it would be wrong to ignore the form in this era. Mixmaster Mike was one of the most decorated DMC champs of the ’90s – he won three consecutive world championships and was rumored to have been asked to stop competing to give younger turntablists a shot. He wasn’t all just technique and flash either; he recorded with the Beastie Boys for a considerable time and released the estimable Anti-Theft Device in 1998. It’s a labyrinthine experience, rooted in hip-hop but unafraid to drift through genres, provided there’s room for Mike to fondle his wax stylishly in the foreground of course.

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98. Grav
Down to Earth
(Correct Records, 1996)

A solid release from the consistent Correct Records, produced by Dug Infinite and some kid named Kanye West, who handled the majority of the album.

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97. Al’ Tariq
God Connections
(Correct Records, 1996)

After 1994’s self-titled album from The Beatnuts, Kool Fash split to go solo as Al’ Tariq. His first album, God Connections, was delivered two years later and further actualized his old crew’s “street hop” canon. The Nuts were heavily credited on production, and slipped in a couple guest verses too (longtime collaborators Mista Sinista and Rawcotiks were also present). Proof that Al’ T was a more than capable rapper, whether grouped up or solo.

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96. Them
(Anticon, 2000)

Dose One’s abstract, kazoo-timbre flow is a take-it-or-leave-it eccentricity. Jel’s beats, on the other hand, still sound as fresh, unusual and essential as they did back in 2000. Samples trip and tumble through the decaying circuitry of vintage machines, and the rigorous templates of standardized rap become a distant memory within the first few tracks. Whether you can handle Dose or not, Them is still worth your time.

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95. MHz
‘World Premier’
(Fondle ‘Em, 1998)

A noteworthy Fondle’ Em single with a whole lot of budding talent under one roof, and a good example of label owner Bobbito’s eye for talent. RJD2, Camu Tao, Copywrite and Jakki all left their marks on the scene in the following years – some more than others.

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94. Krumb Snatcha
‘Gettin’ Closer to God’
(M.I.A. Recording Corp, 1997)

Organized Konfusion and Nas rapped from the perspective of a stray bullet and a gun, respectively, to portray the effects of gun violence on their community. Boston’s Krumb Snatcha, however, shed all of the metaphorical bells and whistles of previous stabs at the topic and vividly chronicled the time when he himself fell victim to a shooting. While his details of the physical and spiritual struggle that ensued seemed a lofty weight for the casual listener to bear, the song was heard everywhere. That well-laced Primo beat didn’t hurt its mobility.

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93. Illogic
Unforeseen Shadows
(Weightless Recordings, 1999)

Ohio stand up: Columbus’s Illogic made his name on the freestyle circuit, before releasing his debut album in 1999 (on cassette, anyway; its full release wasn’t until 2000). More steeped in the battle than later, more eccentric albums like Celestial Clockwork, it was the first taste of an album-length partnership with Blueprint that produced consistent results for a decade to come.

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92. 7L & Esoteric
Speaking Real Words, The EP
(Direct Records, 1999)

You only have to poke your head into Boston to realize how seriously the city took – and still takes – indie rap. This is an area of the US where you’d have to surgically remove backpacks from its legion of 30-something rap purists, and it makes sense that worthy duo 7L & Esoteric emerged from there.

Speaking Real Words has held up surprisingly well, and despite its detractors does a great job of bridging the gap between NY street rap and something a little more Northern. ‘Bound to Slay’ pits Esoteric against a suite of Big L samples, highlighting the importance of D.I.T.C while adding a Beantown twist. Don’t be mad.

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91. Buck 65
(Anticon, 1999)

‘Centaur’ is Buck 65’s best and best-known single from his Anticon days. He went on to enjoy a long career which included major label releases and various genre experiments; his most interesting work might actually be found somewhere among those.

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90. Masters of Illusion
Kut Masta Kurt Presents Masters of Illusion
(Threshold Recordings, 2000)

Sure, Kool Keith’s Dr. Dooom and Dr. Octagon records took the front page and centerfold respectively, but Masters of Illusion, a collaboration with producer Kut Masta Kurt, is something of a pro choice. No ‘Apartment 223’ or ‘Blue Flowers’ to get fanboys frothing at the mouth, but this is a dark, sprawling collection of low-key winners from beginning to end.

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89. Lone Catalysts
Hip Hop
(B.U.K.A. Entertainment, 2000)

Helmed by producer J Rawls (best known for throwing a beat on Black Star’s ‘Brown Skin Lady’ and ‘Yo Yeah’), Lone Catalysts continued the legacy of Pete Rock and C.L. Smooth, combining jazz-flecked instrumentals (Rawls often discussed his very specific sampling technique) with backpack-friendly rhymes. Tracks like ‘Hip Hop’ and ‘Due Process’ were acclaimed for a time – now it feels like having a porthole into a different era.

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88. Molemen
Ritual of the…
(Molemen, 2000)

A well respected Chicago crew throws a rap party and invites some notable rap friends from other cities to join in. This compilation doesn’t really have any loftier goals than showing off some rappin-ass-rapping, and that’s refreshing in an age full of overwrought concept albums and obnoxious sloganeering. It’s telling that one of the best known songs here features Slug, Doom and Aesop loosely doing GZA’s ‘Labels’ routine with video game references. Sidebar: do kids today even know what it means to “put your quarter up”?

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87. Louis Logic
(Solid Records, 2003)

Imagine if Eminem was your next-door neighbor instead of an angsty, world-conquering superstar. That’s the appeal behind Louis Logic’s Sin-a-Matic, one of the laugh-out-loud funniest rap albums of the decade and one unafraid to cover binge drinking, relationships, racism, workplace disputes and everything in between. Blessed with the wit to cut through tough issues and the humor to drag you in, Logic’s debut was as relatable as it was out of place in an urban music landscape celebrating Ludacris and R Kelly’s ghetto fabulousness, and it still holds up over 10 years later.

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86. The Foreign Exchange
(BBE, 2004)

Behold the power of message boards. A rapper and a producer meet on Okayplayer, hit it off, and despite being on separate ends of an ocean decide to make an album together. They work entirely over email and IM, finish the album without ever meeting, and lo and behold – it’s a success.

Phonte and Nicolay weren’t the first to collaborate over email, but they were one of the first to publicize it – and they deserve credit for that, because back in 2004 it felt like a novel and innovative idea. But it would be unfair to put the album’s success entirely on the duo’s work methods. More likely, Connected resonated for the same reasons Little Brother’s The Listening did a year prior, delivering a satisfying dose of thoughtful relatable raps over soul-sampling beats to those who were desperate to keep hold of an ailing scene.

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85. Mr. Len
‘This Morning (ft. The Juggaknots)’
(Matador, 1999)

This beat could have easily been on Little Johnny From the Hospitul or some Co-Flow loosie, though by that point we all knew that the group’s demise was a reality. The same thing that made Prince Paul’s Prince Among Thieves a must-buy was present here: new Breeze bars, and the on-record Queen Heroine that we’d thirsted for since ‘Weight’. Win-win.

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84. Masta Ace
Disposable Arts
(JCOR Entertainment, 2001)

Ace pulled an impressive and nearly unprecedented (at the time) career revamp with Disposable Arts, which is right up there with Prince Paul’s Prince Among Thieves in terms of narrative concept albums. It wasn’t as sonically adventurous as some of 2001’s other hits, but by the same token Ace’s traditionalist approach made the story more accessible, helping it to connect with a wider audience.

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83. Necro
Gory Days
(Psycho-Logical Records, 2001)

Let’s get this straight – it might be hard to take Necro seriously with his shock tactics and non-stop horrorcore imagery, but he’s still a killer producer. He managed to nail both sides on Gory Days, and although the lyrics aren’t for the faint of heart (stand-out track ‘Dead Body Disposal’ gives directions to exactly that), it’s the Canarsie veteran’s most coherent selection of tunes. It’s also worth noting that for all the chat of limb removal and merciless stabbing, he’s a damned creative lyricist.

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82. Dan the Automator & DJ Shadow
Bombay the Hard Way: Guns, Cars and Sitars
(Motel Records, 1998)

There is a good argument to be made that an album of remixes of ’70s Bollywood movie themes doesn’t actually belong on this list. Although Automator’s approach to the material is clearly rooted in conventions of hip-hop production, the results still often sound more like exotic funk than typical instrumental hip-hop of the era. In truth, when the album was first surfaced these kinds of nuances were simply ignored – heads embraced it because it was billed to two indie rap super producers, and the music was different and totally in the spirit of the experimentation that thankfully balanced out our pig-headed orthodox rap ideology.

With Madlib’s influence and a flood of foreign sounds brought on by unchecked file-sharing, this kind of sampling tourism would become far more commonplace, but Bombay The Hard Way was the first to point our ears to far-off lands and make us wonder what other crazy shit could be out there.

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81. R.A. the Rugged Man
Die, Rugged Man, Die
(Nature Sounds, 2004)

It’s probably a stretch to say that without R.A. there would be no Cage, Necro or even Eminem. Still, the man formerly known as Crustified Dibbs certainly has a strong claim to being the original white shock rapper. His early singles – including a legendary lost duet with Biggie – and his reputation for outrageous behavior all made him a legend during indie rap’s peak era. This album arrived a little later, at a point when his persona had already mellowed out a bit, but the somewhat subdued subject matter allowed his considerable technical talents to come to the fore. While there’s nothing quite as lunatic as ‘Cunt Renaissance’, this is his best work overall.

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80. Saukrates / Choclaire
‘Father Time / 21 Years’
(Knee Deep Records, 1995)

Back in ’95 we could have sworn Saukrates was some deep-pitted Brooknam, Wu-affiliate shit. In actual fact he was Canadian, but sounded like a younger, more agile, fouler-mouthed Gza, over that beat – unrelenting in its sinister mode of operation. ‘Father Time’ was the best rap track Canada had churned out before the last five or 10 years (and they were pretty damn early with this coming out in 1995). The Choclair cut was quite good, too.

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79. The Demigodz
The Godz Must be Crazy
(Ill Boogie, 2002)

Punchlines, chopped-up classical music, scratching – The Demigodz may have specialized in rap that appealed to dorm room kids, but they were really great at it. If 36 Chambers felt like hanging with a bunch of rowdy hood dudes, The Godz Must be Crazy did the same for a particularly funny bunch of middle-class rap fans at a time when thugs didn’t smile, let alone laugh.

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78. The High & Mighty
Present Eastern Conference All Stars Vol. 1
(Eastern Conference, 1998)

It’s fashionable to talk shit on The High & Mighty these days, and Mr. Eon was a pretty average rapper, but it’s a mistake to write off their discography entirely. There are gems to be found there, especially when the group was assisted by great guests as they are on this bumper compilation. All sorts of underground luminaries pop up here, from El-P and Mos Def (on the same song!) to Alchemist, Kool Keith and Bobbito. ‘The Bboy Document’ and the songs about masturbation are the ones that most people remember from the tracklist, but there are also plenty of low-key gems, like Smut Peddlers’ excellent ‘One By One’.

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77. Tragedy Khadafi
‘True Confessions / Thug Paradise’
(25 To Life Entertainment, 1997)

If the boys caught you purchasing, carrying, or playing this fucking record in ’97, you would’ve been cuffed and booked on a felony (because that’s what would usually ensue when this aired out of a loud system in an enclosed space). Both joints had New York City and its headlining rap DJs in a frenzy: Stretch propping them as crown jewels of Thug Thursdays (the partly-official show name since he split with Bobbito) and Funkmaster Flex running them regularly on his prime time Hot97 radio spot. While ‘Thug Paradise’ might’ve invented the “Flex Bomb” (Flex always spun it back and got on the mic to say some wild shit), everyone, no matter how jaded and anti-thug they were, could not help but zone along to ‘True Confessions’. Trag went seismic when he hit the era of the “Tunnel banger.”

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76. Dilated Peoples
Third Degree
(ABB Records, 1997)

Before they sold their souls to the majors and signed with Capitol Records (achieving moderate success in the process), LA rap trio Dilated Peoples were a veritable underground concern. ‘Third Degree’ was their first proper 12″, and positioned Dilated Peoples as LA’s answer to a sound that was becoming worryingly East Coast-centric. Sure their style was jazzier and more green-hued than the band’s New York peers, but the angle is clear.

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75. Antipop Consortium
Tragic Epilogue
(75 Ark, 2000)

It makes sense that NYC stargazers Antipop Consortium released their debut full-length on Dan the Automator’s 75 Ark imprint. While they were geographically a country apart, Antipop shared a sense of future-facing experimentation with Dan’s Deltron cohorts, and Tragic Epilogue would set them on a path that would lead straight to the UK’s Warp Records. For our money it’s still their best record, only rarely trading in coherence for experimentation and never losing sight of a New York street rap backbone that would dissolve as they traveled further down the spiral.

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74. Tame One
When Rappers Attack
(Eastern Conference, 2003)

After marking his place in rap history as part of the legendary Artifacts, Tame had a strong second act in the Eastern Conference/Def Jux continuum. These days he is best remembered for prodigious dust usage, and while he certainly made some good music under the influence, he also deserves credit for simply being a damn good rapper.

His style was akin to his cousin Redman’s: vivid, gregarious and humorous. He could tell a story well, and unlike many of his contemporaries was never too hung up on whether or not he was making “real hip-hop.” When Rappers Attack remains the best example of what he had to offer before the drugs became a detriment.

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73. MF Grimm
‘Get Down / Emotions’
(Dolo Records, 1996)

Aside from Harlem’s Children Of The Corn (the group which housed a teenage Cam’ron, Big L, Ma$e, McGruff, and Bloodshed), the island of Manhattan only had about a handful of rappers worth talking about. For heads who knew, MF Grimm was usually first to be mentioned. Grimm was known mostly as a freestyle killer, plus KMD and Kool G Rap collaborator, and he dropped this 12″ via Stretch Armstrong’s Dolo imprint to much jubilation.

While the A-side was well-constructed for a nighttime thug sway and Henny spillage step maneuver (it would probably still be a club banger in parts of Japan, no?), ‘Emotions’ was the fucking gem here. Grimm and collaborator B-1 penned the Infinity Gauntlet of indie rap street anthems (or ’90s street anthems in general, period). Every verse here is perfection, each line immaculate.

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72. Arsonists
As the World Burns
(Matador, 1999)

Arsonists are a great example of how late ’90s indie rap could be tough, kinda nerdy and have a humorous bent all at the same time. As the World Burns includes a song named ‘Lt Worf & Chewbacca’, but you also get the sense that anybody rapping on it could undoubtedly knock you out. The group had an interesting career path – after releasing a few singles on Fondle ‘Em they became one of the few rap acts signed to the indie rock powerhouse Matador.

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(Mush, 2003)

cLOUDDEAD are arguably the biggest act to emerge from the Anticon stable, but there’s debate as to whether they’re even hip-hop at all. The short lived trio of Dose, Odd Nosdam and Why? put together a series of challenging EPs and this sprawling full-length before unceremoniously disbanding, but not before forcing people to re-think their idea of what hip-hop was and could be. Songs would stretch over movements rather than be confined to a few sweet 16s and 32s, and at time it felt like their closest allies were post rockers like Godspeed or Tortoise. Ten still sounds like nothing else on the planet, and that’s to be celebrated.

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70. Mood
(Blunt Recordings, 1997)

Considering it is best remembered for kickstarting the careers of Talib Kweli and Hi-Tek, Doom sounds surprisingly Wu-related. The beats are dark and the raps are frequently tuned to the ‘intelligent street soldier spitting knowledge about the Illuminati’ frequency. We’d put money on at least one camo bucket hat being present at some point of the recording process. By the time Sunz Of Man show up near the end their presence already feels like a foregone conclusion – they were there in spirit all along.

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69. Blackalicious
(Solesides, 1993)

Gift Of Gab rapped his ass off in a different style on each of these Chief Xcel and/or DJ Shadow-produced tracks. The only joint not handled by the two Solesides beatsmiths was ‘Cheezit Terrorist’, an interlude which seemed to be a live radio recording of Gab going apeshit over Black Moon’s ‘How Many MC’s’.

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68. Aesop Rock
Daylight EP
(Definitive Jux, 2001)

Lead track ‘Daylight’ (which also made it to later album Labor Days) worked because backpackers could finally play something for their girl and maybe catch a BJ to it, but things quickly took a turn for the darker as the EP progressed. Shortly after the clever cadence rework from day to ‘Night Light’, Vast Aire appears as a homeless man wiping his ass with the Daily News and sleeping with squirrels, alongside the first real public display of Aesop Rock rapping on an El-P beat. Hear that? That’s the sound of your girl playing snake on her Nokia while you’re just trying to “call, scream phoenix! Click, dial tone.”

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67. Latyrx
The Album
(Solesides, 1997)

Lateef the Truth Speaker and Lyrics Born made up Latyrx (geddit?), and sat at the very center of the Californian Solesides collective. It’s easy to forget after the success of fellow Solesides alum DJ Shadow and the group’s transition into Quannum Projects, that their early material is still just as crucial as it ever was, and just as confounding too. The Album is bizarre and brilliant: it’s conscious, certainly, but never lacks an all-important edge of uncertainty that’s only highlighted by Shadow’s breathtaking production on highlights such as ‘Latyrx’ and ‘The Quickening’.

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66. Various Artists
Farewell Fondle ‘Em
(Definitive Jux, 2001)

There are several moments on this list that represent a passing of the torch from the first ’90s wave of New York indie rap to the second wave that would dominate the early 2000s – this is one of them. Fondle ‘Em either released or paved the way for much of the music mentioned here, and without it this list would literally not exist. It’s only fitting that this tribute to Bobbito’s seminal work, featuring several of the artists in our top 10, was released on a label that defined the later years of the era.

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65. Mister Voodoo
Lyrical Tactics
(Fortress Entertainment, 1996)

Voo and co. waged war against trash rappers and industry politicians. At the time, Natural Elements was one of the crews we could count on to body our tape decks with stellar battle-centric freestyle antics (they never slacked on a radio appearance), then follow-up with a solid record such as this. Noteworthy also for a show stealing verse by their first lady, Essence, on ‘Shine’ – we’re not sure if she’s actually been on anything else.

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64. Murs
(Veritech, 1996)

Side A of this tape is not Murs solo, but old 3 Melancholy Gypsies material (Murs, Eligh, and Scarub) from back when they rhymed fast and had the Project Blowed guys pretty upset. These three tracks made heads over West embark on a grand scavenger hunt as they were desperate to hear more of this faster style (they called it “choppin'”).

It wasn’t long before kids in Cali and Hawaii were circulating tapes of a crew called Log Cabin, a pre-Living Legends teenage outfit fronted by Eligh and Radioinactive (pre-Shape Shifters). In a trade, you might’ve got what seemed to be a different collection of Log Cabin demos (mostly, it was just a variation on song order), but you’d always end up hearing those first two bars of Nirvana’s ‘Heart Shaped Box’ looping in as ‘Sunsprayed’ popped on.

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63. Thirstin Howl III
Skilligan’s Island
(LandSpeed Records, 2002)

Thirstin is one of New York rap’s great oddballs, and this is his definitive work. The man put songs about boosting Polo alongside songs about fucking cartoon characters, living with his mom and being an Alaskan fisherman, and yet somehow this ridiculous combination works. Not only that, it makes for one of the most purely entertaining albums to emerge from the NY underground. It’s worth noting that in the larger historical context, he is also one of the OG New York Latino rappers.

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62. Binary Star
Masters of the Universe
(Subterraneous Records, 2000)

While Detroit’s J Dilla acted as a focal point for Michigan hip-hop at the turn of the aughts, Binary Star’s Masters of the Universe took on boom-bap with a quasi-mystical swing of its own. With post-Wu-Tang track titles like ‘Conquistadors’ and ‘The KGB’, the group fully rocked the “b-boy as shaman” image making its way through college campuses nationwide. At their best though, Binary Star were just great hip-hop: check out the soulful groove on ‘Reality Check’ for proof.

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61. Prince Paul
Psychoanalysis: What Is It?
(WordSound, 1996)

The scene is 1996: 2Pac and Biggie are at war, Nas is accused of selling out with It Was Written, Wu-Tang unleash sonic anarchy and Bad Boy’s funk-pop run New York – and Prince Paul just released a concept album about therapy? With R&B songs about date rape, Schooly D and Luke parodies, trip-hop serenades and more skits than songs, this was the exact moment when Mo Wax/Ninja Tune/alternative turntablist producers cleaved from hip-hop’s mainstream.

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60. Jedi Mind Tricks
Violent By Design
(Superegular Recordings, 2000)

Philly duo Jedi Mind Tricks are best known these days for rapper Vinnie Paz’s controversial viewpoints and obsession with conspiracy theories, but that doesn’t change the fact that Violent By Design still goes. The real star here is producer Stoupe the Enemy of Mankind, who guides us through Paz and on-again-off-again member Jus Allah’s lyrical eccentricities with a barrage of gloomy samples and gut-churning beats. It’s not big or clever, but it’s damn enjoyable.

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59. People Under the Stairs
The Next Step
(PUTS Records, 1998)

LA’s People Under the Stairs had their mission straight on debut The Next Step: bare-bones jazz-flecked hip-hop that showed a keen understanding of what came before. It was enough to position them in the sights of Om Records, who picked them up for the successful run of albums that would succeed this one, but there’s still an honest, lo-fi charm to The Next Step that they never really recaptured. ‘San Francisco Knights’ says it best – it’s sunnier than most anything from the group’s Eastern counterparts, but still just as crunchy and just as powerful.

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58. Peanut Butter Wolf
My Vinyl Weighs a Ton
(Stones Throw, 1998)

Peanut Butter Wolf might be best known as the figurehead of indie hip-hop behemoth Stones Throw, but prior to spending his time cutting checks, he was cutting tunes of his own. His debut album My Vinyl Weighs a Ton finds the producer-selector juggling his passions – sure, he’s put together the tracks himself, but everything’s been smudged by the quick hands of a DJ. There are few banner tracks or obvious singles here and it’s an experience that needs to be listened to from beginning to end. No wonder that he ended up becoming so intrinsically involved with Madlib.

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57. Natural Resource
‘Negro League Baseball / They Lied’
(Ekapa RPM, 1996)

The mid/late-’90s had no shortage of anti-industry/anti-jiggy/anti-“frontin’ ass rappers” raps, but this 12″ did it well for the time. The guy/girl tag-team dynamic worked, with Ocean being the more animated simile machine while What? What? was on a confident, Bahamadia-like, scholarly wave. They also had a video for ‘Negro League Baseball’ which caught daytime play on BET’s Rap City – a big thing back then for any indie artist trying to crack through the mainstream media shell. What? What? later became Jean Grae.

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56. Scaramanga
Seven Eyes, Seven Horns
(Sun Large Music, 1998)

Scaramanga Shallah was Sir Menelik’s “big Willie, truck jewels” rap alter-ego: the type of guy fans of Mobb Deep, M.O.P., Kool G Rap, Pun, and Wu-Tang could get down with. He traded in the disjointed, super-weird prose of the Kool Keith collabs for slang-riddled, rapidly-spoken bars that spanned the length of fly gear, drug trafficking, and – obviously – various mythological gods. While we saw bold shades of this guy on ‘Nightwork’ (credited to Cyclops 4000), this album was the point where he honed in on the style and put forth his loudest, most polished-for-crossover effort. Godfather Don and Showbiz on production didn’t hurt.

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55. Natural Elements
‘Bust Mine / Paper Chase’
(Dolo Records, 1997)

Natural Elements were pioneers of the first wave of (what’s widely referred to as) independent hip-hop. Their earliest handful of records (including the solo 12″s) were a surefire way of telling the underground climate and scene mentality as a whole. In ’96, they were metaphorically bustin’ slugs at the industry and fake rappers (see Mister Voodoo’s ‘Lyrical Tactics’); a year later, things got a bit more literal and frequent with the gun toting.

Natural Elements felt like they had paid dues enough and were right to get on a “taking it” angle. This wasn’t perceived as a sell-out maneuver, though, as those elements (zing?) that had us fuckin’ with A, L, and Voo in the first place were ever-present: tightly knit wordplay, frantically-paced mic passing, and Charlemagne on the tracks (these were probably his sharpest contributions). It marked an interesting point in the underground when folks were dialling back to the pavement of their block as opposed to imagining up new lyrical planets and other wordy shit.

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54. Atoms Family
The Prequel
(Centrifugal Phorce, 2000)

At the crew’s peak, Atoms Family was more like an underground community help group, with each member individually branching out to collaborate and add to the grand intermingling. Cryptic’s studio was like an artist hostel as it often housed folks whether down the road or from far across the country – usually at the same time – for day- or night-long sessions. Stacks of taped cyphers, demos and half-finished EPs were well in abundance, and the names of those involved often read like a video inventory from the sci-fi/horror section of Kim’s Underground (R.I.P.). Unfortunately, for one of the most active crews in New York’s mid/late-’90s underground, most of this material ended up on the cutting room floor.

In 2000, thirsting heads received some solace with the release of this compilation, which gathered a bunch of the finer demos from core Atoms members. Definite highlights: Vast Aire’s finest solo outing (‘Adversity Strikes’), Alaska’s most aggressive solo joint (‘Who Am I’) and a raucous Vordul shouting about “Japanimated wings” (‘Not For Promotional Use’). Yes, that is a pre-Cannibal Ox Vordul, for sure (also ex-Vordul The Immortal Portal Closer).

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53. CunninLynguists
(FreshChest, 2003)

It’s all in the album title: the geography, the ideology and the Outkast fandom. Dropping a few months before T.I’s Trap Muzik changed the face of Atlanta rap forever, Deacon the Villain, Mr SOS and Kno were repping for Georgia in a scene that brimmed with hostility for anything below the Mason-Dixon line. Though the group is still active, particularly in Europe, Southernunderground was their backpack peak, laced with goofy punchlines and heartfelt stories.

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52. J Dilla
Ruff Draft
(Mummy, 2003)

Let’s call this “Dilla goes Nuggets” – a psychedelic garage album that just happens to be built from rap elements. It’s fuzzy and distorted and dirty, but still kinda bouncy too; you can ride to it, but you gotta be packing speed and mushrooms and have a scowl on. The original EP is really all you need – it’s more than satisfying even though it’s very short. The bonus materials included in the re-release don’t hurt, but they don’t really add anything either.

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51. Percee P
Now and Then
(Self-released, 2001)

Percee is undoubtedly a supremely skilled rapper, but his legend in the underground will always hinge on his persevering efforts to spread his work more than on the music itself. His story is familiar to anybody with even a passing knowledge of the New York rap – for years the man stood in front of Fat Beats on 6th Ave and tried to sell this record to anybody who might have an interest in hip-hop. At least three of the people involved in the making of this list bought it from him there. We’re guessing at least a few of those reading this did as well.

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50. Reflection Eternal
Train of Thought
(Rawkus, 2000)

Any indie hip-hop list would be incomplete without Talib Kweli, but while his work with Mos Def has been set in stone, his collaborations with producer Hi Tek are often brushed aside. Train of Thought followed the excellent ‘Fortified Live’ 12″, and while it’s not quite as essential as that unfuckwithable single, it’s still packed with towering moments.

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49. J-Live
The Best Part
(No label, 1999)

The release of Brooklyn rapper J-Live’s debut The Best Part was fraught with difficulties – though it was finished in 1998, it was shelved twice as it got passed between labels, and J-Live pursued a career as a teacher as word of the album travelled from backpack to backpack. Eventually, after bootlegs increased its visibility, The Best Part was finally released in 2001 and stands as a late-period continuation of the classic Gang Starr sound – Primo even threw a beat J-Live’s way for the title track.

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48. Company Flow
Little Johnny From the Hospitul
(Rawkus, 1999)

After coming out with Funcrusher/Funcrusher Plus and changing the way a lot of people approached rap music, El-P and Mr. Len (Bigg Jus had amicably departed at this point) focused their dusty-but-digital sights on the waves of “instrumental hip hop” that were slapping land quite frequently at the time. While not as particle-scattering as DJ Shadow’s Entroducing, this album still caused a heavy shift in perception – El and Len even toured off the release, bringing Def Jux familia Mr. Lif, Vast Aire, and (the incredible) BMS along for the overseas ride. It’s too bad El never released the vocal version of ‘BMS Digital’.

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47. Camu Tau
‘Hold the Floor/Wireless’
(Definitive Jux, 2001)

Listen to ‘Hold The Floor’, take a walk, and try not to hum the hook. Let’s not even talk about Mu’s style and control of language. A shining example of one man’s genius.

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46. Non Phixion
The Future is Now
(Landspeed Records, 2001)

Indie rap supergroup Non Phixion’s debut album probably looks even more insane now than it did when it dropped back in 2001. Not only do we have DJ Premier, Pete Rock and Large Professor supporting Necro on the production side, but there are guest appearances from DOOM, plus members of Fear Factory and the Deftones. It’s a wonder that it actually holds together and even more amazing that it stands as the much-derided horrorcore subgenre’s most coherent moment.

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45. Jurassic 5
Jurassic 5 EP
(Rumble, 1997)

Before Jurassic 5 signed to Interscope and became the world-conquering successors to Pharcyde et al, they released an indie EP that contained most of their best tracks (it was later re-tooled and transformed into their debut album). The Jurassic 5 EP contained ‘Concrete Schoolyard’, ‘Action Satisfaction’, ‘Jayou’, ‘Quality Control’ and more – basically everything you’d want to hear at a Jurassic 5 show in 2015. Not bad for a debut 12″ on the band’s own label.

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44. Dr. Dooom
First Come, First Served
(Funky Ass Records, 1999)

In 1999, Kool Keith was dealing with somewhat unwanted stardom. His Dr. Octagon full-length on ascendent British indie imprint Mo’ Wax had granted the veteran rapper critical and commercial success, so how did Keith respond? By killing off the Octagon character in the intro of First Come, First Served. The album was touted as Keith’s return to street rap, and saw him ditch the stargazing shakes that characterized Dr. Octagonecologyst. Within seconds of standout track ‘Apartment 223’ (still a Kool Keith all-time great), it’s clear that we’re in for something dirt-caked and unshakeably grounded in reality. It’s a bumpy ride, but one that largely holds up today, thanks in part to KutMasta Kurt’s robust set of beats.

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43. Little Brother
The Listening
(ABB Records, 2003)

Little Brother’s debut appeared just as the backpacker era started to wane, and the group became the last bastion of lyrical everyman rap. The album’s aesthetic emulated ’90s traditions and drew favorable comparisons to classic Native Tongues material, which could’ve been a draw or a turn-off depending on how you were feeling about indie rap as a whole in 2003. If you still had a taste for boom bap this was a gold mine, and Little Brother deserve props for being a genuine grassroots success.

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42. Lootpack
Soundpieces: Da Antidote
(Stones Throw, 1999)

If you’re looking to track the genesis of LA legend Madlib, look no further than Soundpieces: Da Antidote. The single, sprawling album from Cali three-piece Lootpack (Madlib, DJ Romes and Wildchild), it’s the first time we got to hear Madlib’s tape-saturated, jazz-indebted, sample-heavy blueprint. At times it’s shaded by naivety and ‘Lib’s slightly less talented collaborators, but his ambition and scope is admirable – just head to ‘Hityawitdat’ and you’ll hear the framework that Madlib dissolved over the course of his genre-twisting Quasimoto debut The Unseen.

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41. Jaylib
Champion Sound
(Stones Throw, 2003)

“I keeps it simple as well as complicated.” This neatly sums up Champion Sound, the sole full-length document of the meeting of two of indie rap’s great minds: Madlib and the late, great J Dilla. It seems strange now that two artists so known for their outside-the-box thinking chose to set barriers for this project, with each track rigidly featuring one of them handling production and the other sticking to vocals, then swapping those responsibilities every other song. The album sounds like a celebration of these two powerhouse producers joining forces, but surprisingly, they’re hesitant to get weird with it. It’s more bottle popping than acid dropping, which seems out of character, especially since both artists handle the latter so well.

Even though Champion Sound is a collaborative effort, the format forces the listener to draw comparisons. It’s not obvious whether this is because Madlib’s production trumped Dilla’s, or if Dilla was just a better rapper, but the majority of the album’s best cuts position Madlib behind the boards and Dilla on the mic, delivering straight-to-the-gut daggers of simplicity. Despite the pair’s differences, however, the transitions and additional short instrumentals between each song make it evident that they were smoking the same strain.

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40. King Geedorah
Take Me To Your Leader
(Big Dada, 2003)

Take Me To Your Leader is 70% guest features over phenomenal Geedorah production, 15% instrumentals spliced with audio clips in old school KMD fashion, and 15% classic Doom solo cuts. So classic in fact, that he truly does come across as a towering three-headed rap monster.

Doom’s guests look like mere humans in comparison with lines like this one: “They’re too carefree with their mouth around here / Off with his head! Display it in town square / On top of a seven feet spike, make sure it’s on tight / And light up when the peasants throw stones with all their might / The skull gets smashed for weeks ’til vulture beaks eat the last meat off the cheeks / Maybe then they’ll know the right words to speak out loud, at home, in the world, or in the streets!” It makes us wonder where Take Me To Your Leader would have landed on this list had it been a DOOM solo effort. But if you must have a feature, please keep Mr. Fantastik – he was wearing his thinking hat (tap, tap, tap, tap, tap.)

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39. Cage
Movies for the Blind
(Eastern Conference, 2002)

Revisiting this album, it’s amazing how appropriate the title Movies for the Blind feels. Cage is an incredibly vivid rapper, and on this album creates a phantasmagoric alternate universe that’s one half unflinching junkie reality and one half ultra-violent nightmare. It’s not actually a big stretch to imagine some of these tracks adapted into grindhouse-era nasties fuck Shia LaBeouf, somebody call early Abel Ferrara.

Ironically, it’s easier to appreciate Movies For The Blind now than it was when it was first released. Back in 2002 we loved this album but didn’t think about it in these kinds of terms – it was just a bugged out drug experience from a crazy motherfucker who beefed with Eminem and had a Shogun Assassin sample on his best single, and was responsible for inspiring more than one indie-rap kid to try dust (true story).

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38. Count Bass D
Dwight Spitz
(Eastern Conference, 2002)

Even though he is generally well regarded, Count Bass D doesn’t get nearly enough credit. He’s not the greatest rapper but he is a great producer; the sampledelic collage approach used on this album predates, and maybe even predicts Madvillainy and The Further Adventures Of Lord Quas. Surprisingly, this was apparently Count’s first attempt to use samples at all – his prior work was built around live instrumentation.

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37. Various Artists
Def Jux Presents
(Definitive Jux, 2001)

This turn-of-the-century split was absolutely pivotal for three reasons. 1) It marked the end of Company Flow, as it contained the last three tracks to be credited to the group’s name. 2) It was host to the first properly mixed and mastered material by Cannibal Ox –before this, there were only mildly clear tape dubs floating about on the message board/AOL chatroom black market (Hawaii, aloha). 3) It was the starting point of El and Amaechi’s Definitive Jux imprint (Rawkus, bye).

While we could argue which side garnered a higher level of anticipation, let’s shift the spotlight to the moment you heard a voice on ‘Simian Drugs’ other than El’s and realized it was Ill Bill shittin’ on all (probably suburban) rappers who had established themselves primarily from an Internet-born fanbase (another first here, as the anti-computer nerd message was much more bullhorn-like in declaration than anything featured on ‘Linda Tripp’). Also, the ‘DPA’ instrumental was a wet dream come true for any fan of Ultimate Breaks & Beats and Vangelis. A thing of beauty, we tell ya.

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36. DJ Premier
Haze Presents: New York Reality Check 101
(Payday, 2001)

New York’s underground scene was not stylistically monolithic – it included a wide range of commingling strains. This mixtape collects some of the key New York singles of the mid/late-’90s and in doing so presents a great snapshot of the variety on deck at the time. You get J-Live dropping lyrical miracles on ‘Braggin Writes’ alongside FT dropping gems of ignorance like “I’m sorta psycho like a retard on a motorcycle” on ‘Metal Thangz’, while Godfather Don finds the midpoint between the two on ‘Properties Of Steel’.

You also get Shades Of Brooklyn doing nostalgic ‘Project Windows’-type rap on their classic ‘Change’, G-Depp doing romantic thug proto-cloud rap on ‘Head Over Wheels’, and of course Company Flow’s seminal ‘8 Steps To Perfection’. The 101 tag in the name is apt: this is an essential entry-level indie rap primer, even if it did come out on a subsidiary of a major label.

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35. Pharoahe Monch
Infernal Affairs
(Rawkus, 1999)

As one half of acclaimed underground rap duo Organized Konfusion, Pharoahe Monch was hardly an untested entity when he made his way to Rawkus in the late ’90s. It may have even been possible to predict the insane breakout success of his Godzilla-sampling single ‘Simon Says’, which still stands as one of the most recognizable tracks of the indie rap era and certainly one of its biggest international hits (it was remixed by Roni Size, dammit). Infernal Affairs has sunk into the background since the glory days of Rawkus, unfairly sullied by Monch’s latter day label woes, but it still holds up. Monch is a dextrous rapper and a damn good producer too, and this record is packed with massive cuts, whether he’s going toe-to-toe with rapper’s rapper Canibus on ‘Hell’ or controversially responding to Common’s classic ‘I Used to Love H.E.R.’ on ‘Rape’.

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34. Hieroglyphics
3rd Eye Vision
(Hiero Imperium, 1998)

What, you thought we were gonna go through a list of the best of indie rap without giving acknowledgement to West Coast legend Del tha Funkee Homosapien? 3rd Eye Vision may have been Del’s finest moment, teaming him with Casual, Pep Love, Domino, DJ Toure and rap golden agers Souls of Mischief. Time might not have treated the album well – head to Deltron 3030 if you want something that’s aged better – but Del’s vision is here in undiluted form. For a porthole into Oakland’s underground rap scene there’s no better document.

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33. Mr. Lif
I, Phantom
(Definitive Jux, 1998)

For his full length debut, Boston rapper Mr. Lif decided go the way of progressive rock and craft a concept album. Considering that directions on how to correctly follow the album’s labyrinthine storyline needed to be included in the liner notes, it would take longer to properly describe the in-depth narrative behind I, Phantom than it would simply to listen to it. To greatly simplify things, it concerns a nuclear holocaust, so who better to handle the majority of the production than Def Jux boss EL-Producto? Lif gets a major A for effort here, but as with other extremely literal narrative projects, it can be difficult to listen to this if you don’t plan on hearing the whole thing in one sitting.

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32. J-Zone
Pimps Don’t Pay Taxes
(Old Maid Entertainment, 2001)

In an ideal world, Pimps Don’t Pay Taxes would have been an underground smash, attracing the attention of Jim Jarmusch and being adapted into a feature film about a bunch of disaffected NYC grumps at the dawn of the city’s Disney-fication. Instead, we have to settle for it being one of the funniest, most cynical SP-1200-based records ever made; a cry of protest from rap outsiders looking in at all the Cristal popping and Casio beats and wondering why they can’t get laid.

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31. Brother Ali
Shadows on the Sun
(Rhymesayers Entertainment, 2003)

Dropping at the peak of Roc-a-Fella’s chipmunk soul era and Atmosphere’s emo-rap, Brother Ali’s Shadows on the Sun bridged the divide, lacing Ant’s crate digging with old school boasts and heartfelt confessionals. Whether narrating life on the block (‘Room With a View’), high school fights (‘Win Some Lose Some’), self love (‘Forest Whitaker’) or just shit talking (‘Bitch Slap!’), Shadows on the Sun was Ali at his most grounded, before the college tours and politics. Listen with an open mind and you might forget it was indie at all.

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30. Edan
Beauty and the Beat
(Lewis Recordings, 2003)

No one could ever accuse Edan of playing to the critics in 2005 when he combined summer of love psych pop and golden age boom bap on Beauty and the Beat, and the genres’ lo-fi grit proved to be surprisingly compatible. If you ever wondered what Prince Paul and Pink Floyd sound like in a blender, here’s your chance.

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29. Quasimoto
The Unseen
(Stones Throw, 2000)

It’s hard to overstate exactly how powerful The Unseen was when it dropped back in 2000. Here was a collage of disparate samples – old jazz and funk cuts, elements pulled from surreal French sci-fi flick La Planète Sauvage, words grabbed from the annals of hip-hop history – that were graced by the deeply unusual presence of helium-voiced rapper Quasimoto, a blunted blue alien who materialized through the dense smoke clouds in Madlib’s studio.

The Unseen needs to be listened to from beginning to end – cherry picking its (few) obvious moments would do it a disservice. Sure, you can get the general idea spinning ‘Bad Character’ or ‘Discipline 99’, but Madlib wasn’t interested in writing singles, he was writing an album in the very classic sense. ‘Lib would travel further into the abyss on the album’s psychedelic follow-up The Further Adventures of Lord Quas, but The Unseen represents a turning point in hip-hop, and hasn’t dated even a day. Spark up and listen.

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28. RJD2
(Definitive Jux, 2002)

There aren’t many instrumental albums on this list (for good reason), but we had to include Deadringer. The MHz producer might have drifted into iffy territory music since ’02, but this album still towers above its peers. His name was already synonymous for a certain seam of quality when it dropped, but this was his chance to shine. It had a few memorable vocal moments, certainly – Blueprint and Copywrite both handle themselves well – but this was a record that shone on its instrumental cuts. Opener ‘The Horror’ is all you need to hear to get you started: RJ was welding together horror samples long before the entire scene was nodding to John Carpenter and Goblin.

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27. Various Artists
Project Blowed
(Project Blowed, 1995)

Focused around LA’s Good Life Cafe in South Central, Project Blowed was an open-mic night that quickly became a hub for the West Coast’s underground hip-hop movement in the ’90s. Overseen by rappers Aceyalone and Abstract Rude, it wasn’t long before the scene was set in stone on an influential compilation album, also titled Project Blowed. Here was a record that highlighted the difference between the East and West Coast underground movements without resorting to name-calling or shot firing; Project Blowed put artistry first and foremost, and the record stands a crucial document of the genesis of a scene that’s still very active.

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26. Godfather Don
Properties of Steel: The Hydra Records Singles
(Hydra Entertainment, 2010)

Don’s most essential release is a tie between the ‘Styles By The Gram’/’Properties Of Steel’ and ‘Piece Of The Action’/’Seeds Of Hate’ 12″s. This Hydra Entertainment comp has both, plus his third (an easy runner-up) gem of a single, and the oft-celebrated ‘Burn’. That stretch of ’97 to early ’98 material was easily his most potent, where he abandoned the playfulness previously interwoven throughout his demos (especially in the production) and went straight to the dark side.

Those joints were completely foaming at the mouth, both in mood and content, and while Don’s tracks had obviously elevated to “free pass to a neck brace” status, his wordplay and cadences jaggedly tore through each beat like trying to mummify a coil of barbed wire in Scotch tape. Dukes wanted you to know how hard he was on that paper chase – inspired enough to commit “illegal actions” and horrific ancient rituals alike. Think of this as the EP we would have loved to have seen drop in official form (tracks four to 10), plus a bonus EP of choice demos and loosies.

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25. Deltron 3030
Deltron 3030
(75 Ark, 2000)

There’s one damn good reason to listen to Deltron 3030 if you’ve somehow manage to avoid it up until now, and that’s the production. It was the brainchild of Californian beatmaker Dan the Automator, and along with Canadian turntablist Kid Koala and Oakland rapper Del tha Funkee Homosapien he managed to bolt together a sci-fi concept album that wasn’t dragged down by its conceit. Its widescreen scope is still impressive 15 years later, and while Del’s rhymes sound painfully old-fashioned at this point, we’re still not sure what Dan was smoking. Whatever it was, we’re interested.

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24. Aceyalone
A Book of Human Language
(Project Blowed, 1998)

At some point on a list like this, you inevitably need to touch on the whole ‘rap as poetry’ thing, so we might as well touch on it here where the allusion is actually apt. In the backpacker scene, especially on the West Coast, poetry slams and spoken word performances were a close cousin of rap open-mic nights. So it’s not really surprising that the best album from a luminary of one of the most famous and influential open-mics plays like a beatnik poetry reading in a smoky jazz café. Dig Acey up on a small stage (black turtleneck optional), breathlessly expounding streams of consciousness as Mumbles grooves on a piano somewhere just outside of the spotlight. His missives are heady and full of symbolism, each an intricate and literary exploration of his personal philosophy. You likely won’t understand them all, at least not after only one listen, but you never doubt that the man really does have something to say.

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23. Mos Def
Black On Both Sides
(Rawkus, 1999)

When you see Mos (sorry, Yasiin Bey) on TV these days its easy to forget that back in ’99 backpackers were frothing at the mouth for Black on Both Sides. At that point in time, the Brooklyn rapper had set the world on fire as one half of Black Star, and his solo turns (on Rawkus’s Soundbombing and Lyricist Lounge comps) had been savored like Beluga caviar. Thankfully the album didn’t disappoint, taking Mos into the stratosphere (‘Ms. Fat Booty’? Get outta here) without alienating his core audience, bringing his sober message to a new set of fans who maybe didn’t own the complete works of Organized Konfusion and a stack of Fondle ‘Em 12″s. Few indie hip-hop albums have so succinctly captured the world’s attention, and as we all know, Mos Def would go on to become a bona fide celeb, for better or worse.

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22. Various Artists
Soundbombing 1
(Rawkus, 1999)

Soundbombing is the first of several wildly popular and influential compilations released by Rawkus, collecting their best and most interesting singles from the mid-late ’90s. Their picks did indeed prove to be winners; a good portion of the rappers and producers featured here would go on to become either cult favorites or outright stars. Later entries improved the formula by including a wider range of artists and more exclusives to supplement previously released material, but Vol. 1 still holds up as both a strong introduction to one of indie rap’s greatest labels and a great mixtape in its own right.

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21. El-P
Fantastic Damage
(Definitive Jux, 2002)

Fantastic Damage is the first solo full-length from ex-Company Flow member and Def Jux founder El-Producto, whose label was, at the time, gaining momentum with every release. Tracks like ‘DPA’ and ‘Simple’ and his production on Cannibal Ox’s The Cold Vein were hints of what El-P might be up to, but even with these advance warnings, Fantastic Damage still caught us by surprise, and somehow managed to make El’s previous projects seem easily digestible.

Building off the already unusual groundwork first laid down by Company Flow, the album took fans deeper into El’s mind. Clocking in at a lengthy 16 tracks, the first listen of Fantastic Damage seemed angled very intentionally to leave listeners baffled. It was an adventure from the jump, and surviving it required two bottles of water, two packs of cigarettes (one menthol, one non-menthol), an eighth of mushrooms, two Krylon cans and a $25 Def Jux trucker cap. It played like a puzzle – something you had to decipher if you were inclined to give it the necessary attention, and a trait that’s consistent in El-P’s music to this very day.

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20. Slum Village
Fan-Tas-Tic (Vol. 1)
(Donut Boy Recordings, 1997)

Recorded by then relatively unknown producer J Dilla (still called Jay Dee) in ’96, Fan-Tas-Tic (Vol. 1) was sold at shows in the Detroit area where it slowly but surely developed a cult following worldwide. By the time it managed a proper release, however, it was almost a decade old – SV had reworked the album for A&M Records, where it was set for release in 1998 but shelved when A&M was bought and dissolved into UMG. In the interim, Dilla’s star began to rise (his work for Common, Erykah Badu and Tribe Called Quest didn’t hurt) but although the record was picked up and released in 2000, it wasn’t until ’05 that we saw the album in its original form emerge.

Fan-Tas-Tic (Vol. 1) is still the pro choice, its ragged almost ad-libbed rhymes sitting perfectly over some of Dilla’s most beloved beats. While the re-tooled and widely loved Fantastic Vol.2 is undoubtedly a classic, there’s something magical about hearing these tracks in their original form. This was Dilla’s vision, and deserves its mythical cult status.

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19. Siah and Yeshua Dapo ED
Siah and Yeshua Dapo ED
(Fondle ‘Em, 1996)

While by ’96 it was clear that Bobbito Garcia (along with Stretch Armstrong) was the East Coast’s FM-dial gatekeeper for burgeoning rap talent of which to follow, it was through Fondle ‘Em Records that Bob was able to give these (mostly) new names a life outside of tape dubs. The fact that he co-hosted the tri-state’s most beloved underground radio show may have placed him at an unfair advantage in terms of inhabiting the top spot in most demo submission lists – no one complained, as the label’s output was nothing short of translating Bob’s meticulous ear for “beyond conventional” rap. Heads could enjoy vets of “89Tec9” (our nickname for NYC’s WKCR 89.9 FM) such as The Juggaknots, Godfather Don, The Arsonists, and Mr. Live, at a much higher playback quality, thanks to these vinyl-only releases.

Siah & Yeshua’s EP, the fifth record for Fondle ‘Em, was put out with similar regard, and to an increasingly warming reception (though, at the time, no one knew what they even looked like). The two weren’t exactly regulars to the radio show, but Thursday late-nighters were well familiar with tracks such as ‘The Visualz’, ‘Gravity’, and an 11-minute / 11-beat opus, ‘A Day Like Any Other’. Siah and Yesh exhibited a back-to-back chemistry which far surpassed most two-man teams of the day – only to be rivaled by Natural Elements’ L Swift and A Butta – especially when given 11-minutes to tell a story.

Production, by Jon Adler, dashed through various realms of jazz with emphasis on switch-ups and the same rhythmic flux which made us snap our necks to The Roots at the peak of their Organix / Do You Want More?!!!??! live era. This record broke not only new talent, but also new tastemaking ground for Fondle ‘Em, cementing their “instant buy” status for future releases to come.

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18. The Cenubites
The Cenubites
(Fondle ‘Em, 1995)

Clive Barker’s Cenobites were “extra-dimensional beings” who were wildly mutilated and did crazy shit. Bobbito Garcia’s Cenubites were rap legends Kool Keith and Godfather Don, both of whom definitely spent time in places other than Earth and most likely did crazy shit, too. Keith, as Rhythm X, counting from 1 to 14 because he could; Don losing his shit on his solo feature (heavy Monch ‘Thirteen’ vibes in the best way possible); dialogue from Johnny Got His Gun over off-kilter jazz drum spasms; ‘Lex Lugor’; yelling; and Fondle ‘Em Records’ label head, Bobbito, rapping as himself. File this under rap opera in the key of “rubber room on a Crazy Eddie blunt.”

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17. Aesop Rock
Labor Days
(Definitive Jux, 2001)

Labor Days, aka the album for which every journalist had to dig deep in the thesaurus to find alternatives to “dystopia.” It’s not far fetched to assume Aesop’s middle school English teacher was blazin’ hot; our guess is that his elaborate, original writing style developed in an effort to get her attention. Give a classroom a free-choice writing assignment, and the smart dollar says young Ian Bavitz’s paper would have been very different from those of his fellow students.

Glancing at Labor Days 14 years later, all the pop culture references and clever turns of phrase and wordplay tricks are finally understood and pleasant to listen to. We can’t wait until 2030 when Skelethon will be just as easy to grasp.

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16. Bigg Jus
Black Mamba Serums 2.0 (Promo)
(Big Dada, 2004)

This oddly specific choice – a promo edition of a reworked re-release of a lost cult item – actually represents a de facto box set of Jus’s best work. Both versions of Black Mamba Serums are included, and by extension this also covers the great Plantation Rhymes EP. So you get the bulk of Jus’s incredible work all in one shot: the heartbreaking and deeply personal tales of a youth escaping the nightmarish realities of his upbringing through graffiti; the heady politics; the super-scientific tongue-twisting braggadocio and odes to the B-boy ethos; the forward thinking production which still feels futuristic a decade later, etc. The only thing really missing is the absolutely necessary ‘You’ve Changed Remix’ of ‘Gafflin’ Whips’. Granted, not all of the material has aged well – certain moments feel painfully dated – but even so, Jus remains the pinnacle of what the more abstract side of the backpacker scene had to offer.

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15. Various Artists
Lyricist Lounge 2
(Rawkus, 2000)

Lyricist Lounge 2 is the second installment of the other compilation series by Rawkus, based on an infamous open mic night of the same name. It was met with mixed reactions upon release since it included a number of established and commercially successful artists; indeed the ‘underground’ tag becomes tenuous for an album that starts with a Biggie freestyle.

These objections made sense in the context of the times, but in retrospect they’re not very well justified. Yes, the compilation takes the spotlight from fledgling artists that could have been included instead of Nate Dogg and Redman and such, but none of the artists featured were far outside the scope of interest for the intended audience – there’s not a shiny suit in sight. Most importantly the music itself was very good – heads simply had to deal with the fact that a few of the songs were just a bit catchier than they were used to.

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14. Atmosphere
Lucy Ford EPs
(Rhymesayers, 2000)

We could have picked God Loves Ugly here, as it was Atmosphere’s most polished effort at the time and arguably their first step toward larger success, but this collection of EPs remains the one. These were the songs passed around by in-the-know rap friends, and the ones being performed at shows where El-P might be lurking in the back, perhaps waiting to jump on stage to do that one hidden track.

By this point Slug was already a seasoned rapper and fully developed in his poetic everyman persona, but still enough of a youthful, boozy miscreant for us to identify with. The more mature God Loves Ugly didn’t constitute a fall off, but you could feel something changing in the air. It sounded like soul searching was eclipsing the blunt smoking; a good direction for their career but not for our tastes. Indeed, from there on Atmosphere would go on to become an indie rap juggernaut, and the token approved rap act for some who weren’t fans of the genre at all. Their success was well earned, but it was outside of the scene as we knew it. Or perhaps just outside of the scene as we wanted it to be.

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13. The Coup
Steal This Album
(Dogday Records, 1998)

While plenty of rap zeroed in on the struggle of poverty, few rappers managed to illustrate it better than Boots Riley of legendarily under-appreciated Oakland outfit The Coup. Rather than counter these struggles with money hungry braggadocio, Riley offered a staunch anti-capitalist message that’s exhibited best by the album’s title. It was a reference to anti-corporate writer Abbie Hoffman’s Steal This Book, and Riley wasn’t making a throwaway reference – his aggressive flow was targeted at the people who were making money in the chain, and he wasn’t afraid to lose listeners in the process. There are plenty of records that dwell on politics in this list, but few rappers handle their message so thoughtfully as Boots Riley. Steal This Album should be on the required listening list for any musician desperate to challenge the system, and it’s never been more relevant than it is in 2015.

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12. Dr. Octagon
Dr. Octagonecologyst
(Mo Wax, 1996)

There are a fair few Kool Keith appearances on this list, but few of his projects have achieved as universal acclaim as Dr. Octagonecologyst. The album was created after Keith circulated a couple of self-produced tracks that reached the ears of Dan the Automator. With help from regular Keith collaborator KutMasta Kurt and turntablist DJ Q-Bert, the duo put together an album that challenged listeners’ perceptions of rap and garnered Keith unprecedented success. With standouts like ‘Blue Flowers’ and ‘3000’ carrying the sound way beyond the usual indie rap rags, Keith quickly tired of the new attention and killed off the character (see entry #44) with his new, harder-edged alias Dr. Dooom in 1999. However, didn’t stop him from resurrecting Dr. Octagon (without the involvement of Dan the Automator, Q-Bert or KutMasta Kurt) in ’06 for the awkward The Return of Dr. Octagon.

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11. Black Star
Mos Def & Talib Kweli Are Black Star
(Rawkus, 1998)

The union of two of underground rap’s finest emcees was exactly as incendiary and brilliant as it should have been. Black Star was labelled as “conscious rap,” but we’d doubt that Mos Def and Talib Kweli would have totally embraced that definition. That would infer that rap music that wasn’t so concerned with Black Star’s overt political stance was unconscious (read: dumb), and to interpret Black Star as such would be to entirely miss their message.

Mos Def and Talib Kweli were educated Brooklynites, and were unafraid to write rhymes that dwelled on the problems endemic in society – particularly white America’s blinkered view of a black community that was as diverse and indescribable as any other. Pride and celebration of blackness was nothing new to the black Brooklyn intelligentsia, but to the legion of white fans who swarmed to buy Mos Def & Talib Kweli Are Black Star (BLACK STAR – it’s in the goddamn name) it was a message they not only needed to hear but to understand. This wasn’t just a collision of classic Rawkus-era beats and so-called “conscious” rhymes, it was a demand for change, and in 1998 that was exactly what we needed.

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10. DJ Shadow
(Mo Wax, 1996)

The sticker on the front of Endtroducing read “DJ Shadow is the Jimi Hendrix or Jimmy Page of the sampler.” This rockist propaganda helped sell an album steeped in hip-hop tradition to a generation of young indie-loving fans, who suddenly had their ears opened to a sound that beforehand had maybe been walled off by divisive rappers or difficult politics. These were the sort of internet forum-savvy fans who’d never listen to Jay-Z but wouldn’t have a problem with the instrumentals. This was never Shadow’s intention – he cut his teeth penning beats for his Solesides crew – but it undoubtedly happened, and inadvertently helped establish a gulf between listeners that’s never really dissipated.

Thankfully, the album itself is good enough to outshine its legacy. Shadow’s skills here remain unmatched, and he achieves the near-impossible in producing an all-instrumental record that’s gripping from beginning to bitter end. A collage of jazz, early electronics, film samples (repeated chops from John Carpenter’s Prince of Darkness are used to tie the record together) and truly massive drums, it’s so damn good you almost forget its sources. If you only listen to one instrumental hip-hop album, it should be Endtroducing.

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09. D.I.T.C.
‘Day One’
(D.I.T.C. Records, 1997)

Between figuring out the “Amsterdam code”*, this joint and the ‘Internationally Known/The Enemy’ 12”, D.I.T.C. kinda smashed ’97. While ‘The Enemy’ shouldn’t be ignored (it’s one of the greatest anti-police records, features one of Big L’s best verses, and one of the most sinister beats DJ Premier has ever laid to wax), this posse cut was the one you just could not escape, whether at the Wetlands on a Tuesday night or as Funk Flex’s “left field selection” (for the real heads) at whatever bottle swingin’ club he was playing at the time.

*Those Netherlanders really loved their rugged New York hip-hop, plus weed was very legal – D.I.T.C. practically had second homes over there.

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08. Various Artists
Soundbombing 2
(Rawkus, 1999)

The second volume of Rawkus’s Soundbombing series is a great collection of songs with impeccable underground cred – the tracklist is just huge. Pharoahe Monch’s ‘Mayor’ is on here and it may be his best solo song; pre-fame Eminem is on here being weird before he got rich off it; ‘Patriotism’ is on here, marking an invisible line in the sand between old Company Flow and El-P’s later solo endeavors; Common is on here, not yet sucking; and ‘Medina Green’ is one of the best songs Mos ever guested on. Those are just the big highlights – there are also smaller gems like Diamond’s incredible ‘When It Pours It Rains’, which really makes the most of two minutes.

More than just entertainment, it was a lesson in the art and science of putting together mixtapes, a platonic ideal of how to compile and combine random rap songs into a cohesive whole. That may sound hyperbolic, but this really is the best and most definitive compilation of the era.

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07. East Flatbush Project
‘Tried By 12’
(10/30 Uproar Records, 1996)

It’s the beat from 1996 that everyone knows – all it took was a koto sample and an Al Green drum loop. Really, everyone knows this beat – if you’ve never heard a rap song in your life, you hum the ‘Tried By 12’ melody whilst doing your laundry. This beat is supposedly being made into a vaccine to fight crippling food allergies. Beluga whales learn how to swim by communicating this beat as sonar to one another. If only you could go platinum by the number of times your instrumental was used for freestyles, live shows, dance battles, Japan (just Japan), etc.

The crazy shit was, most people didn’t know that a vocal even existed (which kinda sucks, cause it was a fucking great song, and video. Also: FUCK (clap) ALL (clap) THOSE (clap) REMIXES.

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06. MF Doom
Operation: Doomsday
(Fondle ‘Em, 1999)

Contrary to popular belief, especially pre-Y2K, Doomsday could not have been predicted. There were just too many factors working against the chance of having any one date on which everything would go simultaneously awry. How exactly was Doomsday to play out, really? Plague? Nuclear meltdown? A super meteor colliding with the Earth resulting in one huge planet enveloping explosion? Zombies riding on dinosaurs? World War 3? The point is that any outlying catastrophic event waiting to happen takes time to gradually work out the world-killing results/effects.

MF Doom took on this element of unpredictability and concept of time gradience when he weaved together Operation: Doomsday – his first, and finest, solo album. Everything here was “man in a box” level anti-protocol, anti-industry, and anti-society. The way in which Doomsday was produced was completely fucked: from mostly sampling less-coveted, for the time, ’80s funk (plus Steely Dan, Isaac Hayes, Scooby-Doo, and The Beatles), right down to combining said samples with drum loops from hip-hop classics with random live-triggered fills and snare hits for more off-kilter spice. Everything sounded like it was stripped right out the tapedeck of a dusty 4-track recorder. Doom, himself, slurred off every verse with an aged alcoholic’s tongue, yet managed to deliver every bar to maximum punchy effect.

When Doomsday came out, it created somewhat of a divide amongst his followers. On one side, there were those who really liked what this new, Dr. Doom-referencing rapper was doing, musically. Then there was the other half who knew MF Doom was previously Zev Luv X of KMD (a guy who, seven years prior, made a song called ‘Peachfuzz’). Perhaps some of us were left wondering what had happened to create Doom – and was Dr. Malachi York with his backyard pyramid somehow involved? While KMD’s Black Bastards album, shelved by Elektra for its “controversial cover art,” shed a little more light on Doomsday‘s PTSD atmosphere, Doom was inadvertently schooling us to how much could happen in a year’s time. Shoot to three years short of a decade and you’re left with a man who has returned from the void, yet still remained completely off the grid, to unveil a masterpiece drenched in misanthropy and urban legend. It was thanks to Operation: Doomsday – and perhaps the three previous Fondle ‘Em singles leading up to the album, too – that MF Doom became an underground icon to actually achieve a level of real life comic book character worship.

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05. J Dilla
(Stones Throw, 2006)

This was our cut-off for the list, the last great and truly significant backpacker album and one that paradoxically added some nails to the scene’s coffin. By the time of Donuts’ release, the rigid exclusionary approach to rap that characterized much of the era’s later years was already becoming archaic, and those still clinging to it were rapidly falling out of step with the times.

The cult of so called ‘Dilla stans’ spawned by his final opus only worsened the general attitude toward the associated sub-genres of indie rap and hastened their decline from popularity and critical relevance. Simply put, somewhere around this time ‘backpacker’ started to become a derisive term. Fortunately that has nothing to do with the actual music on the album, which remains one of the greatest instrumental hip-hop records ever made.

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04. Company Flow
Funcrusher Plus
(Rawkus, 1997)

When tracing the origins of the backpacker movement, Company Flow’s music is akin to the cave painting from which sprang the entire history of art. In fact, when brushing the dust off Funcrusher Plus and reflecting upon its impact, it feels fitting that the cover art features primitive aliens standing by caves. If the totality of rap as we knew it in the mid/late-’90s was traveling on a ship in one direction, Company Flow were on a canoe, quickly paddling in the other. Upon pressing play, the album radiated a sound that either captured you with its originality or made you immediately reach for the stop button. Jam-packed with pop culture references and SAT words, Funcrusher Plus was likr the rush you get when attempting to focus on one single blade on a high-speed ceiling fan. It wasn’t getting jiggy, it was tagging trains. It didn’t pack Uzis in the army jacket lining, it was “fucking with your theology like Darwinism in the bible belt.”

Unfortunately for those captivated, unless your residence was in the Tri-State area, locating Funcrusher Plus was extremely difficult. Finding Company Flow’s music became a scavenger hunt. If you somehow happened to catch ‘8 Steps to Perfection’ or ‘The Fire in which you Burn Slow’ and they piqued your interest, you had to really dig hard to take the rest of that 18-song journey down the tongue twisting road to b-boy heaven.

Proclamations of independence on the CD artwork only accentuated the rebellious tone and made you want it that much more. Under the tutelage of the lyrics, the newly minted acolytes came to despise the corporate fat cats for withholding Company Flow from their local record stores. “Who else is making music like this?” the fans wondered, and who was trying to hide that information? Thankfully, CD burners and Napster were right around the corner, but for a while there it was rough going, like looking at crude stick figures and hoping that they would materialize into a colorful tableau.

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03. The Juggaknots
The Juggaknots
(Fondle ‘Em, 1996)

The calmly-spoken mantra of “Breeze Brewin is actually one of the best rappers of all time” is the fifth element of underground hip-hop.

Moments like his breathlessly-delivered analogy of writing and performing rap as a difficult childbirth on ‘Troubleman’ is pretty mind-blowing for lyrics nerds. But it’s not just Brewin’s unrivaled wordplay that makes The Juggaknots (often referred to as Clear Blue Skies) one of the most celebrated and perhaps even best release in the storied Fondle ‘Em catalog. Beyond the pyrotechnics is an aching humanity, and this is what really connects with the listener.

The album often skews toward conceptual storytelling, but unlike the sci-fi adventures of their contemporaries, the concepts Juggaknots create are grounded and drawn from everyday life. It’s Brewin’s real life experiences of working with troubled teens, not the tongue-twisters, that make ‘Loosifa’ so vivid and poignant. ‘Romper Room’ is a meditation of ghetto childhoods gone wrong – a common rap topic that Brewin’ elevates by thanking his father for instructive ass-whoopings that helped him stay on the straight and narrow. The conversation between a racist father and his son on ‘Clear Blue Skies’ rings true not just for somebody who has shared a similar predicament, but to anybody born into an old-fashioned and close-minded family. There’s even an overreaching life-death cycle superimposed over the (original, not the later reissue) tracklist – it starts with the aforementioned birth allusion on ‘Troubleman’ and ends with the senseless death caused by a love triangle gone horribly wrong on closer ‘I’m Gonna Kill U’.

The Juggaknots left a piece of their heart on every track. That’s what makes the EP so special, and that’s what gives it resonance beyond the confines and trappings of the genre. As street level and NY-centric as it was in its specific content and language, indie hip-hop hardly had a moment that tied together more people across the board, no matter their background or music taste.

PS. The thing about Brewin being one of the best rappers of all time really is true. See ‘Generally’ for further evidence, it’s a song that is going to be studied by future historians as a premiere literary artifact of the early 21st century.

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02. Madvillain
(Stones Throw, 2004)

Madvillainy, or rather a splice of it where the early leaked versions ‘Figaro’ and ‘Money Folder’ are swapped for their respective official versions, has been the cause of plenty of debate while penning this list. There are those among us that believe it deserves the number one spot on this list, being arguably the signature moment from the signature rapper and signature producer of the entire movement.

In terms of rhyme and syllable structure, no one writes like Doom, and through brilliant sample chops (and herbal assistance from the stickiest of the icky), Madlib understood how to sonically complement the spirit of the character wearing the mask, a task no other producer (including Doom himself) has been able to match. Their chemistry makes Madvillainy something very different and very special. It’s the Michael Jordan right-to-left-hand switch layup of classic rap albums – Doom could have written those rhymes to the highlights from his Special Herbs instrumental series and it would have been a slam dunk; Madlib could have used those samples on a Quasimoto project (or any other Stones Throw album for that matter) and it would have been an easy score. Put those two veterans at respective peaks of their skill together, though, and the world gets to experience pure magic.

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01. Cannibal Ox
The Cold Vein
(Definitive Jux, 2001)

The Cold Vein is clearly number one” rolls off the tongue so easily in 2015, but things weren’t always so clear cut. Back in 2002, initial reception to its release was not as fawning as current attitudes might imply. At the time it was seen by many not as a singular entity but another big step in the ongoing ascendancy of the mighty Def Jux. El-P’s production garnered a large share of the praise, and fans trained to reward signifiers of profundity clamored for Vast Aire’s twisted impressionistic visions but rejected Vordul’s directness as simplistic. The overall consensus was undoubtedly very positive, but nobody was ready to put this thing on a pedestal quite yet.

Then the rest of the decade happened. A proper follow-up never materialized – instead we heard rumors of squabbles and creative differences and were hit with the bizarre Speakeroxx/The Ox Below CDR in ’04. Vast alienated his fans with a string of increasingly patchy releases, and while Vordul won a cult following with great solo work, he unfortunately succumbed to personal demons. Through it all people still wanted more Ox, and the mixture of tumult and uncertainty served to slowly inch the group’s debut towards a mythological status.

Ironically it was the rising retroactive distaste for the backpacker era and its denizens that finalized the album’s ascension. Negatively skewed memories rendered the early 2000s scene as the province of pasty suburban white boys spouting untenable stubborn ideologies via boring, self-indulgent screeds. With that derogatory (and wholly erroneous) point of view in mind, it’s only natural that two black Harlemites trading elaborate street scriptures over some of the era’s most progressive production became the beacon of everything redeeming about this period in the underground.

So does the album really deserve the praise and legendary status? Fuck yeah it does, even if it’s far from the only viable contender for this top spot. Vast’s contributions don’t sound as fresh as they did in ’01, but there’s no denying that his style was unique, and the imagery he created sticks to this day. Vordul’s verses have aged much better; in fact you might still be able to find things you missed in them on your first 200 or so listens. El-P’s production hasn’t dated at all, time just caught up with it. Abstracted from the surrounding circumstances it is still an amazing piece of rap music, and it really is the cream of what this era had to offer. Just don’t take that #1 spot for granted.

Read this next: The 100 Best Albums of the 1990s

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