​Photo illustration by Jefferson Harris for Okayplayer.
Photo illustration by Jefferson Harris for Okayplayer.

Rediscovered: The Roots, 'Things Fall Apart'

Okayplayer takes a look back at the pivotal album that saved The Roots from obscurity and helped make them a household name.

February 2025 marks 26 years since the release of The Roots’ 1999 studio album, Things Fall Apart. That year also saw the launch of Okayplayer.com. Initially conceived as an online home for The Roots, Okayplayer quickly grew into a haven for a community of fans, musicians and budding journalists who’d coalesced around the band.

Never fitting in comfortably with the overarching sound and image of mainstream rap, during this time, The Roots found themselves in a contradictory position as a band. As critical darlings whose albums under-performed commercially when measured by the platinum and gold standards of the day, The Roots’ early years were marked by the looming threat that if they couldn’t sell records, they might not survive as a band. 1999 would prove to be a landmark year for The Roots as both the creation of Things Fall Apart and the launch of Okayplayer had major implications for the band’s identity and future.

It’s fitting that the group named their breakout album after Chinua Achibe’s 1958 novel, Things Fall Apart. Much like Achibe’s exploration of Nigeria under the yoke of British control in the 1890s, Things Fall Apart, the album asks important questions about the nature of community and culture. What happens when a community or a culture is threatened by outside, alien forces? Why do the victims of those incursions so often turn their trauma into pathology? How can a strong and functioning sense of community protect against encroachment and oppression? Obviously, there are no sure answers to any of these questions, but what we are left with is a snapshot of a band and a culture in transition. Chinua Achibe’s novel demanded that its protagonists hold onto their cultural customs in the wake of the arrival of Europeans who sought to destroy them, Things Fall Apart raises a similar call to hip-hop culture. As with any art form that comes into contact with capitalism, hip-hop in 1999 found itself being pulled by the opposing forces of creativity and profit. In the wake of rap music’s emergence as a commercial force, it further distanced itself from the culture that produced it.


Despite their present standing as one of hip-hop’s most beloved legacy acts, The Roots have always been an anomaly in the genre. By the time the band’s founders, drummer Ahmir “Questlove” Thompson and rapper Tariq “Black Thought” Trotter met at Philadelphia School for Creative and Performing Arts in 1987, the very idea of a live hip-hop band was a novelty. While The Roots — who were going by the name “Black to the Future” at the time — would go on to become hip-hop’s most significant live band, they were not its first. Contrary to popular myths about early hip-hop emerging as a result of a lack of musical training and education among the inner-city youth, live instrumentation has been a part of the music since the first rap records were made. In 1979 the first wave of rap records like Sugarhill Gang’s “Rapper’s Delight,” Lady B’s “To The Beat Y’all,” and Spoonie Gee’s “Spoonin Rap” and more were made by using live bands to recreate grooves similar to the records that the DJs were playing at the hip-hop jams.

The difference between these bands and The Roots is that these bands were made up of musicians who’d been recruited by the label to do session work. The Roots were a self-contained ensemble who wrote their own material in the studio and built their reputation on the road. As the ‘80s gave way to the ‘90s, hip-hop production was dominated by gritty, sample-based production crafted on machines like the EMU SP1200, and AKAI’s S-950 and MPCs series. On stage, the turntable still reigned supreme with the majority of live rap performances consisting of an MC or group rocking with a DJ playing instrumental versions of their songs. With the exception of Brooklyn-born sextet, Stetsasonic — who released their final album Blood Sweat & No Tears in 1991, nearly four years before The Roots’ major label debut — The Roots seemed to be constantly swimming against hip-hop prevailing sound and aesthetic.

Seemingly at odds with mainstream rap music, The Roots still found success in the early part of their career. Their albums were never big sellers but Do You Want More?!!!??! and 1996’s Illadelph Halflife received critical acclaim earning a four and four and a half mics in The Source magazine’s coveted five-mic review rating system. Outside of The Source, The Roots were generally perceived as critical darlings who had yet to hit upon a sound that would translate into commercial success. When Things Fall Apart was released on Feb. 23, 1999, hip-hop was enjoying a cozy, new relationship with corporate America. The genre had fully integrated itself into mainstream pop culture with artists like Jay-Z, DMX, Will Smith, Lauryn Hill and many more releasing massive sellers the years prior. In this era of the rap blockbuster, the pressure for major label hip-hop acts to strike gold — preferably platinum — on the charts had never been higher. As an outlier in rap, this pressure to sell records was even more pronounced when it came to Thompson, Trotter and The Roots. For rap acts, the unlikely feat of selling millions of records often came at the expense of their artistic vision and often required a “softening” of an artist’s sound or a compromise of their creative ambitions. As the last standing hip-hop band, who made music that did not readily fit into the sound that ruled commercial radio, The Roots were fighting a war on multiple fronts. At its core, Things Fall Apart tells us that The Roots were both anxious about their place in hip-hop as well as hip-hop’s place in mainstream culture.



"We had given most of our adult lives to that point to the band. What if success never came to us, or never came in the form we expected? — Ahmir “Questlove” Thompson from Mo’ Metta Blues: The World According to Questlove.


Spike Lee’s 1990 musical drama Mo’ Better Blues follows an emerging, contemporary jazz trumpeter and his struggle to uphold the integrity of the music in the face of exploitative club owners, interpersonal strife within his band and fickle audience tastes. Things Fall Apart opens with a sampled bit of dialogue from the film that speaks to the state of The Roots as a commercial and creative entity and their place within hip-hop. Bandmates Bleek Gilliam (played by Denzel Washington) and Shadow Henderson (played by Wesley Snipes) debate the nature of Black art and creativity in a world where serious Black art is undervalued, even by Black audiences.

“But we don’t even come to see our own, man… If we had to depend on Black people to eat, we’d starve to death,” Bleek deadpans coldly, while a collage of brief musical moments sampled from The Roots’ prior release appears and dissipates in spurts in the background.

Shadow counters Bleek’s assessment and makes the argument for a populist approach to art.

“Bullshit! It’s all bullshit. The people don’t come because you grandiose muthafuckas don’t play shit that they like. If you played the shit that they liked, then the people would come, simple as that!”

To settle this debate, The Roots turn to none other than Public Enemy’s media assassin, Harry Allen. In a clip taken from the 1996 NPR audio documentary Hip Hop 101: On The Road With The Roots, Allen offers a succinct diagnosis of the problem that ails Shadow and Bleek, The Roots and Black artists everywhere:

“Inevitably, hip-hop records are treated as though they are disposable. They’re not maximized as product … not to mention, as art.”

This dynamic dance between the group’s artistic vision and commercial ambitions is examined and explored throughout the album’s run time. Songs like the opener, “Table Of Contents”, “The Next Movement” and “Step Into the Realm” recall the bright, jazz-rap of Do You Want More?!!!??! and some of the darker, street-oriented album cuts from Illadelph Halflife. Veterans of both the stage and studio by this point, the group possessed the skill to revisit some of the musical terrain they had traveled in the past while experimenting with new sonic avenues.

The jaunty, jazz-guitar-driven standout, “Dynamite!” benefited from blistering guest verses from ELO The Cosmic Eye and a beat produced by J Dilla. “Dynamite!” marked one of the first times The Roots employed a track produced by someone outside of the band and its inner circle, proving that the band could find power by tapping into the broader community of musicians around them. Foreshadowing the collective approach that gave Things Fall Apart part of its core identity, Things Fall Apart’s greatest success came through collaboration and the unlikely union of the experimental and the accessible.

“You Got Me” was Things Fall Apart’s lead single and is to date, The Roots' biggest single. With an instrumental composed by keyboardist/producer, and former bandmember, Scott Storch, a chorus penned by the up-and-coming singer and poet, Jill Scott, and sung by “neo-soul” goddess Erykah Badu, “You Got Me” is a melancholic rap ballad about a romantic relationship in turmoil. Bittersweet and undeniably catchy, “You Got Me” made waves on the radio and served as a perfect setup for Things Fall Apart. Toward the end of the song, Questlove throws a curveball by playing a skittering, double-time drum beat, tipping his hat to the U.K. drum n’ bass sound that the band had been exposed to while living in London in the summer of 1994.

Another key element to “You Got Me”’s appeal was a guest verse from West Philly-born rapper, Eve (billed here as Eve of Destruction). Along with future stars, Bilal, India Arie, and Musiq Soulchild, Eve made her way into The Roots’ orbit by attending the now-storied jam sessions at Questlove’s house at 23rd and St. Albans Street in South Philly.


With the Things Fall Apart sessions underway and a teeming community of artists around them, an unlikely set of circumstances would bring gifted South Philly MC, Beanie Sigel into the fold to record his classic debut verse on the song “Adrenaline!” At age six, Trotter accidentally burned down his family’s house in Philly’s Mt. Airy section, forcing the Trotter clan to relocate to South Philly. There, Trotter and Sigel met during their elementary school years, became friends, and performed in a group together. In the summer of 1996, Beanie Sigel began working with MC/Producer, Shawn “Air Smooth” White of the group Divine Beings on a series of demo songs in hopes of securing a record deal. Not only did White provide Sigel with a space to record, he had a crucial connection with Sigel’s long-lost childhood friend, Black Thought. Thought had met White and the Divine Beings crew at the legendary Philly hip-hop showcase, Rap Underground North, and the two got close. When The Roots were recording Things Fall Apart, Black Thought was surprised to find out that his old friend Beanie Sigel was the brilliant new MC that White had been working with and raving about. With Black Thought, Beanie, Dice Raw and Malik B playing an increasingly intense game of lyrical one-upmanship, the song plays out like a four-way death match between a handful of the city’s most elite MCs. Peppered with guest performances from D’Angelo, The Jazzyfatnastees, Common, Ursula Rucker, Yasiin Bey, DJ Jazzy Jeff, and Lady B, Things Fall Apart’s tracklist reflects just how connected the anomalous band from Philly actually was.

It was the strength of the album’s collaborations and the band’s artistic community that drove it to achieve the commercial success that had eluded them up until that point. “You Got Me” went on to win a Grammy for Best Rap Performance by a Duo or Group and earned the band a gold plaque for 500,000 copies sold in April ‘99. On the eve of the album’s release, The Roots launched another project that would further build upon the community they’d marshaled for Things Fall Apart and change the landscape of internet culture. Okayplayer.com was designed by writer and Philly native, Angela Nissel. Thompson initially conceived of it as a website for The Roots, but Nissel and Roots member, Rahzel had a broader vision for the site as an online community for fans and artists. A few years prior, artists like the Beastie Boys and Oakland rap crew Hieroglyphics launched popular sites that allowed them to communicate directly with their fans. It was clear that the future of the music business would require artists to maintain a direct line of communication with fans via the Internet. The brilliance, humor, knowledge and hubris that users brought enlivened the Okayplayer message boards. This energy helped The Roots build on the community that they had cultivated throughout the making of Things Fall Apart and beyond.


Today, The Roots enjoy a rare status among hip-hop acts. Having navigated a veritable minefield of industrial and cultural shifts, The Roots are now a paragon of longevity in hip-hop. As the breakout release that proved that the band could tastefully dance between creativity and commercial appeal, Things Fall Apart helped make The Roots a viable entity. Nearly 2 years after Things Fall Apart’s release, the group served as the backing band for Jay-Z’s landmark MTV Unplugged album. By recreating the biggest hits by the biggest rapper in the world, The Roots not only displayed their versatility, they proved the accessibility of the sound that once made them outsiders. With over a dozen albums, tours, festivals, films, and their nightly gig supporting Jimmy Fallon on The Tonight Show, The Roots’ penetration into popular culture would’ve been impossible to predict back in 1999. The odds-defying feat that The Roots pulled off has not only served the band, it changed how Black hip-hop artists could exist in the music business. Looking back 26 years later, Black artists from Little Brother and Pink Siifu to Kendrick Lamar and Liv.e and countless others have directly benefitted from the musical space that The Roots carved out. Ultimately, things did not fall apart for The Roots. By sticking to their guns and nurturing a community around them, The Roots not only created a classic, they made it easier for all of the mavericks and outliers who came after them.