Otis “Madlib” Jackson is one of hip-hop’s true eccentrics. The Oxnard-raised, L.A.-based producer rarely gives interviews, and he cultivates an enigmatic presence enhanced by his formidable catalog. 

Over the past two decades, he has released so many albums, vinyl-only 12-inches and mixtapes, and adopted so many pseudonyms that even dedicated fans have trouble keeping up. While he may not have the same pop reputation as peers like Kanye West and Pharrell Williams, he is widely considered one of the best producers of his era. 

Madlib led a generation that disappeared down the rabbit hole of crate digging for rare grooves

That reputation is largely due to Madlib’s talent as a self-described “loop digga.” He has a style that’s deceptively simple, yet hard to duplicate: He makes beats out of samples from rare vinyl, and locates the choicest seconds-long lick in a given song. However, he creates his tracks with an askew personality that sounds like nobody else.

On Lootpack’s only full-length album, 1999’s Soundpieces Da Antidote!, he manipulated his voice so it sounded as if he had swallowed a canister of helium, and renamed himself Quasimoto. For a time, listeners didn’t know that Quasimoto was actually by Madlib. His trick was apparent by 2000 and Quasimoto’s The Unseen.

Yet that wondrously strange album had more going for it than vocal tics. He sampled from ‘60s jazz performers such as Sun Ra and Weldon Irvine and instead of crafting hard-hitting boom-bap drums like, say, Pete Rock, he arranged his drum patterns into a leisurely tempo that accentuated the weirdness of the jazz melodies he used. One of his masterstrokes is “Come On Feet,” which is essentially a cover version of Melvin van Peebles’ “Come on Feet” (from Sweet Sweetback’s Baadasssss Song: An Opera). Madlib blends together his unaltered voice with his helium-filled Quasimoto alias into a kind of bizarre duet, and then interrupts both with van Peebles’ manic, gasping vocal. The trio of voices unfurl over a lengthy loop of composer Alain Goraguer’s work on the science-fiction animation Fantastic Planet, and halting drums lifted from Little Feat’s “Fool Yourself.”

Throughout his career, Madlib has balanced occasional buoys into the mainstream spotlight with experimental work

Madlib led a generation — others include Cut Chemist and Madlib’s brother Michael “Oh No” Jackson — that disappeared down the rabbit hole of crate digging for rare grooves. When he emerged in the late ‘90s, most rap producers stuck to mining classic soul, funk and boogie-oriented rock. But as their palettes grew sophisticated, they begun championing more exotic finds such as ‘60s and ‘70s psychedelic music from India, Nigeria, and Brazil along with  “library music,” incidental music recorded for use in TV commercials and film soundtracks.

Madlib lies in the sweet spot between rap genius and quirky musical anomaly

Under the pseudonym of the Beat Konducta, Madlib recorded a series of instrumental suites like Beat Konducta in Africa and Beat Konducta in India and his 2011 underground hit with Freddie Gibbs, “Thuggin’,” is based around a sample of an obscure British library recording.

Throughout his career, Madlib has balanced occasional buoys into the mainstream spotlight with experimental work. He has produced tracks for Erykah Badu and Talib Kweli, and his 2014 full-length with Gibbs, Piñata, made a surprising debut on the Billboard Top 40 album chart. Earlier this year, Kanye West lit up social media when he released “No More Parties in L.A.,” where he rapped alongside Kendrick Lamar on a Madlib beat.

Yet Madlib’s fans inevitably gravitate to the weirder stuff. On jazz side projects such as Yesterdays New Quintet, he plays all the instruments himself, and then samples those instruments so that they resemble a tonal free-jazz stew. And his techniques have occasionally turned brain-fried.

For Madvillain, which he formed with the equally elusive MF Doom, Madlib concocted a blitzkrieg of comedy routines, spoken-word joints, and private press jazz and funk. Released in 2004, Madvillainyis considered one of the best albums of the 2000s, and serves as further proof of how Madlib lies in the sweet spot between rap genius and quirky musical anomaly.