Bronx rapper Kool Keith cut his teeth as part of influential ‘80s rap crew Ultramagnetic MCs before embarking on a solo career that birthed bizarro rap classics Dr. Octagonecologyst, Black Elvis/Lost in Space and many more. Laurent Fintoni meets up with the legendary lyricist to talk about 2000’s underrated Pimp To Eat, a collaborative album with Ice-T, Pimpin’ Rex and Marc Live.

The year was 2000 and rap was, for the first time, the biggest selling music in America. Among the hundreds of albums released that year was Analog Brothers’ Pimp To Eat: 16 tracks recorded in a week by five guys huddled inside a Beverly Hills studio which, from the outside, looked like a spaceship. They rapped about technology, sex, and hair styles over beats created with old drum machines and synthesisers. It was an analogue album at the cusp of the digital age, a demented blast from rap’s past in the face of its gold-toothed future. Like most things “Kool” Keith Thornton has been involved with throughout his tumultuous career, the Analog Brothers shouldn’t have happened – but it did.

Ice-T first met Pimpin’ Rex in the early ‘80s on the corner of Crenshaw and Slauson in South Central LA. Rex was selling homemade plant holders when Ice drove by in a red Porsche and recognised the hustle. The pair bonded over music and breakdancing. In 1988, Rex sang the hook to Ice-T’s ‘I’m Your Pusher’ and then helped with production for Body Count, Ice’s heavy metal detour.

Meanwhile Keith, who’d met Ice during rap’s ‘80s boom, left New York for LA in the early ‘90s. He was soon followed by his cousin Marc Live, then a member of Raw Breed. There they met Rex, who’d been collecting music equipment in his garage studio since 1977. As for the fifth member of the group, Black Silver, an upcoming rapper and friend of the other members – he was in the right place at the right time.

One day, Rex and Keith called up Ice to tell him they had a concept: the Analog Brothers. Also, they needed to use his studio. The five named themselves after vintage equipment — Rex Roland, Keith Korg, Ice Oscillator, Marc Moog, Silver Synth — and got very high. The album came out, people scratched their heads, the brothers performed one live show, and then they were gone.

Analog Brothers Kool Keith

“You don’t have to follow the same formula as everybody. Just be weird” Kool Keith

Pimp To Eat was reissued by Mello Music Group earlier this year and so on a hot June day I find myself on the corner of Gerard and East 161 in the Bronx outside the Crown Diner. The disheveled restaurant stands in the shadow of Yankee Stadium, two flags above its entrance — one American, one Greek, both trashed — hanging limp in the heat. Inside, past the donut counter, Keith is sitting at a booth by the open kitchen, halfway through a lunch of fried chicken. He’s clad in various shades of blue — navy blue denim cap, arctic blue T-shirt with colored stripes, washed out jeans, white sneakers. Next to him is Sharon, introduced as his girlfriend, in an emerald green dress and with long curly hair that unfurls down past her shoulders. I greet them, slide into the booth, order a coffee, and press record. The Analog Brothers was a collaborative album, but Keith remains the most fascinating character involved – so if you’re going to write about it, you might as well speak to Keith.

According to Discogs, Kool Keith has released 31 albums since his official 1997 solo debut Sex Style, not including aliases such as Dr. Dooom and Dr. Octagon for which he is still best known. On 2012’s Love And Danger Keith recorded a song called ‘Goodbye Rap’ and, having survived two generations of hip-hop but staggered through the current decade, there was talk of his retirement. Since then, however, he’s released two more albums and a string of one-off tracks. Looking at him across the table – big pockets under his eyes, face slightly puffy – Keith looks old, the embodiment of legacy. I ask who brought the Analog Brothers together and for a split second he’s not sure what I’m talking about.

“It happened through Rex, the project kinda came together overnight. Rex did most of the production and we rapped,” he remembers. “It was a big analog sound. Old sound but brand new octaves. Old sounds converted into rap form.” Keith talks like he raps, and raps like he talks, his pauses feel like rhythmic punctuations and the ends of his sentences like punchlines. He asks Sharon to get him a bottle of mango and passionfruit juice from the car and, on her return, pours it over an ice-filled styrofoam cup.

“My nightlife in LA was commercial, but my daytime was underground” Kool Keith

Keith’s a man of dualities: late ‘80s hardcore rapper and ‘90s poster boy for out-there lyricism; self-proclaimed inventor of ‘horrorcore’ (Gravediggaz might have something to say about that) and ‘pornocore’ (no doubts there); and an artist who bypassed a deep fracture between East and West Coast rap by beginning his career in NYC as part of Ultramagnetic MCs before going solo after moving to Los Angeles. His early solo material and aliases were recorded and invented in the decade he spent in southern California, beginning sometime in the early-to-mid ‘90s.

“LA was more open minded musically and creatively,” he says, sipping on his juice. “I felt less complete after my break with Ultramagnetic, I wanted to do other music. I got signed to Capitol and they gave me $500,000 to move to LA.” At first Keith lived in a two-bedroom apartment in Beverly Hills with his then-producer “Kut Masta” Kurt Matlin, who produced the original Dr. Octagon demo, mixed Pimp To Eat, and worked with Keith for most of the following decade. TR Love from Ultramagnetic, Brooklyn’s Sir Menelik, and Marc Live and his Raw Breed group slept on the floor.

Keith likes to talk about the LA days. To hear him tell it, he was living the dream: a Bronx kid with a half-million dollar deal and the City of Angels as his playground. He’d take out $3,000 a day, buy Versace shirts, catch up with his old friend Ice, indulge his porno interests, and party in nightclubs with Shaquille O’Neal and the Chicago Bulls. “It felt like I’d graduated,” he says, happy. “I’d won my championship. Scottie Pippen is next to me buying a tequila sunrise. Together. I felt complete for a second.” For all his talk of ignoring the realities of “the underground struggle” at the time, including requests to come down to the Project Blowed freestyle sessions, Keith’s days were filled with recording what would become underground rap classics. He admits it. “My nightlife was commercial, but my daytime was underground.”

At this point the conversation begins to zig-zag erratically through his memories: the time he was spotted in Roscoe’s House of Chicken and Waffles by Orlando Anderson, the late Crip involved in the investigation of Tupac’s murder, and Empire actress Taraji P. Henson who revealed their love of his solo work; signing to Columbia; when Puffy called to get him off his deal for a “rock band alternative” project with Busta Rhymes; the billboard of his face on Sunset Boulevard. What was the billboard for? “Just a picture of me, something famous,” he replies casually. “That’s what I did everyday. I felt faraway and famous.”

After Dr. Octagon came out in 1996, Keith was a paragon of indie rap dreaming of celebrity status. The majors didn’t know what to do with him but wouldn’t release him from his contract, so he created new aliases, signing deals left and right. “[The major labels] wanted to do something opposite of me, like clothes I’d never wear,” he says, still exasperated at the idea. Clothes matter to Keith. “You see me coming into the office with Macy’s bags but you gonna make me wear a robot suit?” Sharon, who was paying attention at first, has checked out and is staring deep into her phone.

Analog Brothers Kool Keith

For all the dreams of fame Keith might have harboured, Analog Brothers was yet another DIY effort. The album was named Pimp To Eat because they were, according to Ice-T, “On some pimp shit and the ultimate pimping is just pimping ‘cos you hungry.” The original cover was improvised after the group walked into a supermarket and began grabbing various items from the shelves — boxes of cereal, rice, a bag of oranges — before posing as if caught mid-shoplifting. The final touch was a Photoshopped picture of space at the end of the aisle. They wore pimp costumes, if pimps were dressed up by a five-year old or a very stoned adult: aviator jackets, red fur coats, black cowboy hats, and orange hair rollers. Costumes had always been one of Keith’s specialities. “When I left NYC, I left every rapper just trying to look like a rapper instead of an entertainer,” he says. “I bought a lot of punk records as a kid. I bought funk shit, Ohio Players, Slave, Cameo. I didn’t buy covers with rappers on them. I bought a lot of covers with creative clothing on them. So that rubbed off on me too.”

The intensive recording sessions for Pimp To Eat were, by all accounts, competitive. “You’d go in the booth while everybody was sat there writing their own lyrics,” says Rex, who sings on the album. “Black Silver [and I] locked in. He was a space kinda writer and I was flexible,” adds Keith by way of explaining the dynamics of a group imagined on the spot. “It was good for Ice, it made him go in a chamber he’d never been in. He even said it made him feel more interested in writing.” Discussing the rhyme style on the album, Keith says it was “ahead of its time. I don’t hear rappers still on that wavelength or cadences.” He complains that rappers are still obsessed with money, but that’s also what the Brothers talked about. Their style was based on the same boasts rap has always been built on and their subject matter ticked all the boxes — sex, fame, riches. And then they also just plain made shit up, adding a side of Y2K fever and technological lexicon for good measure.

On the subject of current rap, Keith is subdued but at least not as curmudgeonly as most rappers his age. He imitates Future’s rhyming cadence and mimics a chorus built for the club, chanting “throw the donuts up!” before making his point: “It’s better than hearing somebody get super lyrical.” He thinks Desiigner’s ‘Panda’ is a catchy song, too: “You walk around the house singing it to yourself.” Kids today are making new words up, just like the rappers they look up to. “[Desiigner’s] not pronouncing all the words – black X6 sounds like black excess, he’s saying it short, that’s the way to do it now. They don’t care. Youth catches that. It’s all kinds of wordplay. Rappers the only ones that can do intricate speak but uneducated, they let you get away with it.” After all, it’s not like rappers have never made words up. “Remember ‘fo sheezy’ and all that?” Keith asks, before bringing up a late-night conversation with Bay Area rapper E–40 that doubled as a lesson in new slang. “[E-40] was going somewhere and said, ‘watchu marinating to tonight?’ Marinating? ‘Yeah, we gon’ crackalate or something?’ I didn’t know what he was saying but I knew what he meant. It was fly. He had me.”

Analog Brothers Ice T

Rap is defined by the youth of its time but Keith remains defined by the strange glories of his fame-seeking past. What would it take for kids today to relate to his work? “Odd Future, Tyler and all that, they are saying just anything. I think I opened the doors for groups like that, rapping about all kinds of shit and making it sound totally ill.” Keith has tried to adapt in recent years, working with new beats and new talent including his nephew. “You gotta look at it like baseball,” Keith asserts, looking through the window and pointing at the street. “You can’t lock out the new hitters coming up today. You can’t be mad, you just gotta adapt.” And while the quality of this new material is definitely in the ear of the beholder, he’s at least keeping his mind open. “How you not gonna give that person a chance?” he asks rhetorically. “Somebody gave you one. That’s very crazy. A lot of people mad about how people rap. It makes me work harder, go write something crazier. You don’t have to follow the same formula as everybody, you can do all kinds of stuff. Jump on it. Just be weird. Just be wild.”

There is a generation gap in rap today that didn’t exist before. Artists like Keith, Ice, and Rex have careers stretching back four decades and the gap with the newcomers will continue to increase. All we can hope for is an understanding between both sides that their motivations are often the same – making money, having fun – and that they share more similarities than differences. “Back in the days you felt more popular ‘cos your hit record was all in the cars,” Keith says. “Now you go home and see your record in every computer. It’s in all the computers.”

“This album was created in the last days of analog when digital took over, so it is the story of an era,” Rex adds, punctuating his email with emoji from his smartphone. “It’s a reminder to the digital age of what was once a warm sound that hit the ears and vibrated the body in a different fashion.”

I ask Keith if he finds smartphones useful. He says he’s got to buy a new “digital one” before flipping the question around on me, appearing uncomfortable for the first time. He segues quickly. “Why won’t people carry a CD but they want a big ass record? That’s what kills me.” The juice in his cup is empty and the diner has started filling up with school kids looking for a sugary or fried rush. Keith seems to be dozing off. As we wrap up our conversation, we shake hands and Keith tells me he’s off to buy some jeans, a smile across his face. I stand up after him, pay for my coffee, and watch as the analog brother walks out into a digital world.

Laurent Fintoni is on Twitter.

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