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.

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.

By 1997, before the sessions for Things Fall Apart began, drummer and bandleader ?uestlove was exploring new opportunities beyond the Roots. He was more concerned with recording D’Angelo’s Voodoo and Common’s Like Water for Chocolate than he was with his own group. It wasn’t that he wanted to leave the Roots, but still, his outside projects created resentment amongst band members who questioned his focus. “In my head at that time, the notion of a Roots album was a distant third,” ?uest wrote in his 2013 memoir, Mo’ Meta Blues. He was spending time with Voodoo engineer Russell Elevado, learning new ways to manipulate sound to give his own music a more granular, less studied feel. He wanted to be a heralded producer like DJ Premier and J Dilla, but his band’s work felt remarkably clean—even sterile__—__in comparison. The best rap of that era had to feel at least a little gritty: Though the Notorious B.I.G. was signed to Bad Boy, his 1997 album Life After Death had plenty of dark, violent narratives. The Wu’s massive double album, Wu-Tang Forever, was full of woozy street bangers, courtesy of the group’s production team, with the RZA at the helm. Realizing he needed to improve as a producer, ?uest learned how to play drums “dirty,” taking Dilla’s lead and dragging his percussion just a bit to make the beat seem off-kilter.

The genesis of Things Fall Apart can be traced back to a hangout ?uest had with Premier, Dilla, and D’Angelo, where he played them a rough version of a Roots song called “Double Trouble” and got disinterested head-nods in return. Determined to bolster the track, ?uest recorded drums to two-inch tape, looped it back through the soundboard, and tweaked the EQ to give it a feeling of distance. “It was a turning point in my understanding of my own career,” ?uest wrote in his memoir. “I knew that the other guys respected me as a drummer… but I also wanted them to respect me as a producer and a songwriter.” In its finished form, “Double Trouble” is arguably the centerpiece of Things Fall Apart; rapper Black Thought finally had a hard-charging instrumental to match his verbal dexterity, and guest Mos Def matched him bar-for-bar.

Things Fall Apart is where the Roots figured out who they were—it wasn’t “just another Roots record,” and if the group was going to fail, they were going out their own way. “Table of Contents (Part 1)” illustrates their new willingness to take risks: The breakbeat is messy and the mix is intentionally pinched and lopsided, but the track’s feeling of chaos is an ideal table-setter, opening the record on a tense and uncertain note. On “Step Into the Realm,” the drum loop fades in and out, but the rhythmic instability makes the rappers’ audibly distorted vocals sound even more urgent. If the Roots’ first three albums mastered the meeting point between jazz and rap, this was the first time the band went psychedelic, opening up new possibilities sonically and lyrically.

D’Angelo’s 1995 album Brown Sugar and Erykah Badu’s Baduizm from 1997 were the blueprint for new-school soul music, and Things Fall Apart applied those ideas to hip-hop proper. In this aesthetic space, artists with different approaches could find new ways to be creative together, and a new movement was being born. “You Got Me,” the lead single from Things Fall Apart, found a crooning Badu next to rapper Eve from the Ruff Ryders over a lilting guitar figure and strings. The classic arrangement and eclectic mix of voices, paired with ?uestlove’s typically propulsive and cutting backbeat, sounded both old and new, looking backwards and forwards simultaneously. The Roots were pushing the limits of their sound, establishing a lane for D’Angelo, Common, and Badu to do the same. By building a musical community and mastering the art of collaboration, they figured out how to cross over and keep their soul intact.

Things Fall Apart was the Roots’ most successful record, and after years in the shadows, they were finally getting radio airplay and touring as headliners. The album went gold two months after its release and hit platinum in 2013. In addition to its commercial success, it served as a launching pad for new voices, like Roc-A-Fella rapper Beanie Sigel, who debuted as a guest artist on “Adrenaline!,” and Eve, whose “You Got Me” appearance was her most prominent feature at the time. The relatively unknown Jill Scott wrote the chorus for “You Got Me” and was slated to sing on the track until MCA Records pushed for a bigger name (Badu) to appear in her place; soon, Eve and Scott would release their own platinum-selling albums.

Despite being a breakthrough for their band and their scene, the Roots didn’t immediately build on Things Fall Apart’s success. Powered by D’Angelo’s sultry “Untitled (How Does It Feel)” video, Voodoo became a phenomenon, and ?uest spent most of 2000 on tour as the singer’s drummer. By the time the Roots re-grouped, ?uest’s closest peers were pushing their sounds to new places. D wanted to learn guitar; Common and Dilla wanted to experiment with electronic textures. The Roots responded by moving away from the movement they helped create; their follow-up record, Phrenology, was essentially the anti-Roots album, with a heavy emphasis on rock. And while it alienated the Roots’ core fanbase, Phrenology performed well, pushing the group further into crossover territory. The Roots became a more regular presence on TV and radio. Soon after, Rahzel and Malik B. left the group for good. In 2006, Dilla died at age 32 from complications of lupus, and the Roots’ album of that year, Game Theory, kicked off a series of releases with a darker tone, including 2008’s Rising Down, 2010’s How I Got Over, and 2011’s undun. Having secured a gig as Jimmy Fallon’s backing band—first on “Late Night,” then on “The Tonight Show”—the Roots finally and completely entered the mainstream. But they used the freedom to experiment and make the music they wanted.

Things go in cycles, and the approach the Roots pioneered came back around. In 2015, the “next movement” the Roots mentioned on Things Fall Apart seemed to arrive. Kendrick Lamar’s To Pimp a Butterfly—a densely lyrical and allegorical exploration of Blackness and struggle, set to a live-jazz soundtrack featuring dozens of collaborators—is hard to imagine without this album in its rearview. Artists like Robert Glasper, Thundercat, Terrace Martin, and Kamasi Washington channel the same creativity as the Roots, D’Angelo, and company, banding together to push rap, jazz, soul, and more into atmospheric new places. The spirit of Things Fall Apart is in the air.

Looking back on it now, this record feels like both a love letter and a fond farewell to the Roots’ early days, acknowledging that they needed to evolve to stay relevant. And some of the album’s continued relevance is painful. Its closing poem, “The Return to Innocence Lost,” details the fate of a young man seemingly doomed to fail since birth. He dies tragically, leaving nothing but thoughts of a life that could’ve been. Nowadays, black men are dying at the hands of police with alarming frequency, and we’re left to mourn the dead in hashtags and shared articles, wondering what’s next—or who’s next—in this seemingly endless war. Things Fall Apart imparts a similar tone, even if the band didn’t address those issues directly. The black and white cover art, taken in Bed-Stuy, Brooklyn in 1965, depicts a young black woman running from a waiting police officer, her face twisted in fear. The scene is sadly familiar 50 years later. As the Roots teetered between fame and purgatory, virtue and failure, Things Fall Apart captured the intensity of a group with everything to lose and the world to gain.