In 1999, the Roots were in limbo. The Philadelphia hip-hop band had released three critically acclaimed albums but were still considered something of a novelty act, featuring a big guy with a big Afro on drums (?uestlove), a sharp but unshowy MC (Black Thought), two beatboxers (Rahzel and Scratch), and a stellar live show—all anomalies in the gilded age of Puff Daddy and the million-dollar sample clearance. The Roots had by this time amassed a faithful cult following, but none of it translated to mainstream success. They were selling more records and slowly moving beyond their dedicated base of jazz and traditional rap purists, but their career wasn’t headed anywhere in particular.
Reflecting these tensions, 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.