Back in the day, hip-hop was an alternative to mainstream music and culture. But when, in the late ’80s, it became the mainstream, the more indie-minded innovators explored different paths — and created some of the genre’s finest albums.
— DE LA SOUL, 3 FEET HIGH AND RISING (1989) With their decidedly unmacho take on rap and open criticism of their tougher-than-leather peers, this Long Island trio blazed a trail for generations of rap dissenters.
— BEASTIE BOYS, PAUL’S BOUTIQUE (1989) After creating the frat-rap scene with 1986’s Licensed to Ill, the white boys in the hood stepped up with this masterpiece rich in layered samples, left-field references, and some of the most enduring lyrics in hip-hop history.
— DIGITAL UNDERGROUND, SEX PACKETS (1990) Two years before Dre looted Parliament Funkadelic on The Chronic and established the G-funk style, there came this trendsetting, funky, hysterical gem (featuring the debut of Tupac Shakur).
— A TRIBE CALLED QUEST, THE LOW END THEORY (1991) Arguably the best rap album ever, Low End fused jazz grooves with smooth, stark poetry and scaled new musical and lyrical heights that few hip-hoppers have ever matched.
— GANG STARR, DAILY OPERATION (1992) With DJ Premier’s mind-blowing sonic trickery and Guru’s irrepressible flow, Gang Starr were one of the brightest lights in the New York underground, creating innovative art out of urban grime.
— THE PHARCYDE, BIZARRE RIDE II THE PHARCYDE (1992) The Cali crew showed that West Coast MCs weren’t all thugs on this debut LP, with one of rap’s best love songs (”Passin’ Me By”) and the funniest dis track on wax (”Ya Mama”).
— DIGABLE PLANETS, REACHIN’ (A NEW REFUTATION OF TIME AND SPACE) (1993) Oozing jazzy cool, the mixed-gender collective added a sensitive, soft-spoken touch to Tribe’s ingenuity, creating an irresistible groove that united urban hipsters everywhere.
— DR. OCTAGON, DR. OCTAGONECOLOGYST (1996) From his days in Ultramagnetic MCs, Kool Keith was one of rap’s most innovative lyricists. As Dr. Octagon, with DJ Shadow, Q-Bert, and Dan the Automator on the decks, he dropped this brilliant offbeat manifesto.
— COMPANY FLOW, FUNCRUSHER PLUS (1997) With raw, dense beats and intense, dark lyrics, Flow were the perfect antidote to Puffy’s hip-pop parade and a launching pad for MC/producer El-P, who would go on to form indie-rap label Def Jux.
— BLACK STAR, MOS DEF & TALIB KWELI ARE BLACK STAR (1998) Multitalented rapper-actor Mos Def burst on the scene alongside equally talented MC/DJ Kweli on this passionate debut full of eloquent street poetry.
— THE ROOTS, THINGS FALL APART (1999) Building on Stetsasonic’s rap-band concept, the Roots ruled alt-rap once this breakthrough disc, their fourth, bubbled up to the mainstream.
— JURASSIC 5, QUALITY CONTROL (2000) After seven years in L.A.’s underground scene, J5 dropped this stellar debut, rich with old-school harmonies and samples.
— CANNIBAL OX, THE COLD VEIN (2001) Out of the ashes of Company Flow, Def Jux dropped several of the best rap releases of the last two years, including this El-P-produced masterwork.