This weekend marks 20 years since The Roots released their fourth album, Things Fall Apart. In celebrating the album’s 20th-anniversary, Questlove spoke with Urban Legends‘ Maxwell Dartey to break down Things Fall Apart, track-by-track. That oral history is a journey that takes place in Philly, New York City, and Detroit. The creation involves several studios and ties to other legendary Soulquarians albums made at the same time. Quest’s re-telling includes audio Easter Eggs, plenty of references to influences, and some news about J Dilla’s work with The Roots.

Approaching February 23, 1999, The Roots had enjoyed some high praise for their previous album, 1996’s Illadelph Halflife, and its breakthrough single, “What They Do.” Despite the accomplishments, the Philadelphia, Pennsylvania group was not satisfied with its position in Rap. The Roots’ band-leader, drummer, and producer Ahmir “Questlove” Thompson remembers, “We were kind of near the 400,000 [sales] mark, and we felt that ‘What They Do’ would have finally like brought us to platinum,” he remembers. “It didn’t happen, even though the video was loved. We decided that this next album was going to be a do-or-die moment.”

That pressure led the group, longtime affiliates, and a host of musicians into Quest’s living room to flesh out pre-production ideas. The Roots convinced their label to get two passenger vans, a ton of music equipment, and hire a chef from local Zanzibar Blue Jazz cafe. They wanted to lure in friends to jam through free meals and cool gear. Recalling those Friday night gatherings, Quest remembers, “Pretty much the entire Philadelphia music community turned out for free food and instruments. We pretty much conned everybody into jam sessions.” In the days that followed, Questlove, Tariq “Black Thought” Trotter, Leonard “Hub” Hubbard, Kamal Gray, Malik B, and a host of local musicians whipped up the sounds that would ultimately make up the band’s game-changing Things Fall Apart album. But that was only the beginning of a making-of story as epic as the resulting music.

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Diving into the album’s introductory track, “Act Won (Things Fall Apart),” Questlove explains how Chinua Achebe’s 1958 novel, Things Fall Apart, related to the group and, more specifically, MC Black Thought. “We were trying to figure out what to name the album, and Rich [Nichols] and I were sitting in the Sigma Sound reception area talking about Tariq’s rhyme style.” Nichols had mentored The Roots, managing and producing them before his 2014 passing. “Tariq was already set in his ways of being a lyricist’s lyricist and not necessarily a user-friendly lyricist, and Rich was like, ‘Tariq reminds me of that character in [the novel] Things Fall Apart.’ I went out to get the book and Rich explained to me that Tariq was basically a very skilled warrior lost on his own homeland.”

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Quest’ expounds on the connections between Black Thought and the story of “Okonkwo” in Achebe’s text. “We were the American Hip-Hop act that would play any and every festival, any and every show in Europe. We were willing to do the gigs [that] all the other acts weren’t willing to do. Like when Wu-Tang [Clan] messed up [on] the Rage Against The Machine Tour, ‘call The Roots.’ When Biggie and them won’t go to Finland, ‘call The Roots.’ We were always the dependable, will-show-up-and-do-the-gig-type group, and people appreciated us for that. The way that Rich saw Tariq was that he was a very skilled warrior who came back to his homeland only to realize that his traditions and ways have been ruined by settlers and missionaries—similar to the story of Things Fall Apart.” The title stuck, as Black Thought continues to prove his excellence to a cavalier mainstream 20 years later.

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Further in the oral history, Ahmir remembers Rich Nichols’ thoughts just before the release of the album, and his parting thoughts. “I’ll never forget [Rich’s] words. He was like, ‘Hip-Hop is celebrating winners right now. So if this keeps up, it’s only going to be about the winners.’ The last thing that Rich said to me, before he died in 2014, was, ‘My goal was never to take you guys or include you guys [in] the winning circle. I don’t want you guys to win. But I definitely want to guarantee that you’re gonna be the last people to lose.’”

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With a title in tow, sessions moved from Midtown Philadelphia’s Sigma, where David Bowie recorded much of Young Americans, to a New York City lair made famous by Jimi Hendrix. At Electric Lady Studios in Greenwich Village, The Roots collaborated with peers including D’Angelo, Mos Def, Common, Erykah Badu, and J Dilla (who then was still known to most as “Jay Dee”). Questlove recalls, “[J] Dilla was too brilliant for you to ever get jealous, or for you to feel a certain way. He was so brilliant that you knew he was God, and you just accepted it. [If] anyone else tried to flex on me, I’d start seething with jealousy, or feel competitive, or feel like ‘I could beat you!’ But Dilla was so brilliant that you couldn’t beat him, and you just accepted it.”

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At the time, Dilla witnessed Questlove working with D’Angelo on Voodoo cut, “The Root.” The Slum Village co-founder heard a riff by guitarist and bassist Charlie Hunter, who played both instruments at the same time. Fixated, Dilla went all the way back to Detroit to recreate the music for “The Root” in full. To Questlove’s shock and awe, Dilla did so to perfection, purely off of memory. To try and best Dilla’s mastery with the Hip-Hop competitive spirit, Questlove tried to attempt the same feat. The musician-turned-author remembers, “I [was] just trying to see if I [could] at least be as good as Dilla was and try to memorize that song. ‘Cause of course I’m playing on that song, so I should know how to do it. It was a colossal failure.”

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Dilla’s influence did not end there. In dissecting the backstory to the album’s second track, “Table Of Contents (Part 1 & 2),” Questlove reveals that the record was planned to be four parts instead of two, and with Dilla’s name on the bill. Additionally, he reveals that Dilla’s work will be found on The Roots’ long-awaited next album. Dilla, who died in 2006, is credited with producing “Dynamite!” on Things Fall Apart. Shortly after his passing, The Roots bookended Game Theory with collaborations they made with James Yancey.

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Elsewhere in the oral history, Quest’ remembers recording “You Got Me.” He recalls fighting to keep one of the song’s writers, Jill Scott, on the album version. “The problem with ‘You Got Me’ was the label was like, ‘Finally, you’re going to give us a song that’s going to help you hit one out the park. Strike one is we love the hook, but why don’t we get a real celebrity to sing it?’ They just looked at Jill, and said like, ‘there’s no way in hell you’re gonna tell me that this girl’s a star  She sings good, but let’s go with the sure-shot person. Let’s [redo it] with Erykah.’ Thanks, Captain Obvious. She’s red-hot right now. Let’s go with her.'”

Questlove reveals that the creative dispute led him to step away from the revisions. “I insisted like, ‘No man, Jill’s singing this sh*t.’ The label was like, ‘Nope; we want Erykah to do it.’ I was like ‘[Then] I’m not gonna supervise it,’ so [engineer] Bob [Power] was like, ‘Okay, I’ll fly down to Dallas and do it myself.’” The drummer also reveals that he added the Drum & Bass music near the close of the song to tie into the overseas popularity of the genre.

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The song earned The Roots a Grammy for “Best Performance By A Rap Duo Or Group” one year to the day after Things Fall Apart was released. However, the win was bittersweet.

Questlove recalls, “People always ask why I keep the Grammy in the bathroom. The short story is Moby kind of joked on the red carpet that he’s presenting the Rap award, and he loves Busta Rhymes so much that even if he loses he’s still gonna say [that] Busta Rhymes is the winner.” In the midst of his Play success, Moby showed his dismay at the podium when Busta and Janet Jackson’s “What’s It Gonna Be” did not win the category. Questlove and The Roots noticed. “The look of disappointment on [Moby’s] face when he wasn’t going to read it, that’s one thing, but he says, ‘And the winner is…’ and he takes his time opening the envelope, and he says very begrudgingly, ‘In theory… The Roots.’ When I watched it the next night, I asked my ex-girlfriend what does ‘in theory’ mean, and she explains it’s kind of like by technicality. ‘You’re the winner, but not the winner.’ What it did was it literally prevented [me] from really watching that ever again. So to this day, 20 years later, I’ve not watched my highlight reel. [Moby] only recently found out how much that sh*t hurt our feelings, and he feels horrible about it.”

Still, when Questlove’s company is using the commode, they can see The Roots’ first Grammy. They have since won two more related to their Wake Up! album with John Legend.

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Throughout the interview, Questlove divulges a ton of cool facts surrounding Things Fall Apart. It has now been five years since the Philadelphia squad released their last album, …And Then You Shoot Your Cousin. However, as discussed in the Urban Legends oral history, End Game is still happening.

Read Questlove’s entire oral history, song by song, here.

Fans of The Roots can find Black Thought’s reflection on J Dilla and other related videos at AFH TV. We are currently offering free 30-day trials.