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The Roots opened their fourth studio album, Things Fall Apart, with dialogue from a scene from Spike Lee’s 1990 film, Mo’ Better Blues, in which characters Bleek Gilliam and Shadow Henderson—played by Denzel Washington and Wesley Snipes, respectively—debate the state of jazz music. Gilliam doesn’t want to sacrifice his creative vision to pander to crowds, and he thinks black people should come to his shows simply because he’s making black art. “That’s bullshit,” Henderson quips. “The people don’t come because you grandiose motherfuckers don’t play shit that they like.” The clip seemed to acknowledge the Roots’ reputation: They were too smart for their own good, too self-aware, and they were getting in their own way. It was as if, from the very beginning, the band sought to be misunderstood, to find somewhere to hide from the mainstream.

As unique as the Roots were—they were a hip-hop band, after all—their music still had traces of what was popular at the time. Their 1995 album Do You Want More?!!!??! featured the sort of laid-back jazz feel that Digable Planets had perfected the year before on Blowout Comb. The Roots’ follow-up, 1996’s I**lladelph Halflife, was more aggressive and confrontational, taking lyrical and sonic cues from the Wu-Tang Clan. But the group was searching for something different. Before the release of Things Fall Apart, they had positioned themselves as a sort of remedy for the excesses of Bad Boy’s empire, which in those days became an all-too-easy target for the backpacker set. In their satirical 1996 video for “What They Do,” the Roots mocked the sort of rap video stereotypes popularized by director Hype Williams, thumbing their collective nose at champagne bottles and mansion parties. Acts like the Roots wanted to give listeners the “real shit,” but while they and others criticized Bad Boy’s gravitational pull, their art-rap aesthetic was its own form of marketing. They just hadn’t figured out what they were selling. While the Roots thought of themselves as the anti-establishment alongside acts like OutKast and the Fugees, those groups sold millions of records when the Roots were struggling to go gold. - Pitchfork