How Questlove Became the Defining Drummer of His Generation

Questlove / Illustration by Jon Stich

The following is an excerpt from the book Backbeats: A History of Rock and Roll in Fifteen Drummers, released on November 11th.

The 41st Grammy Awards were held on February 24, 1999, and the event was suitably colossal. Shania Twain, celebrating her world-bestriding album Come on Over, performed “Man! I Feel Like a Woman,” while Céline Dion won Record of the Year for the perma-hit “My Heart Will Go On.” Alanis Morissette and almighty Madonna sang onstage and left with hardware that night, in an event that was inevitably touted as the “Year of the Woman.” But none of these icons were as feted as Lauryn Hill, whose debut solo record became the first hip-hop Album of the Year winner, one of five golden phonographs that Hill took home, tying the record for a woman at the time. The Miseducation of Lauryn Hill was already a critical and commercial sensation. Now the Recording Academy said it was equal to prime Stevie Wonder too. Hill was 23 years old.

She spent nearly enough time onstage that night, speaking and performing, to fill a sitcom-length bit of television by herself, and in the dozens of names that Lauryn Hill listed and thanked, one casual mention, “Ahmir,” was easy enough to miss. But Ahmir was certainly watching that broadcast, keenly aware of the significance of this moment for hip-hop and for pop music history. He was also feeling uneasy and anxious, though that wasn’t strange for him.

Ahmir Thompson is better known as Questlove (at the time, “?uestlove”), drummer and figurehead for the Roots, who were then an ascendant Philadelphia hip-hop group known for their live instrumentation. Their musicianship was beyond question, and any young American who regularly saw music outdoors at the time surely caught a Roots gig or two at least (guilty). The group knew Lauryn Hill from years as co-headliners, tour mates, and friendly competitors with her group, the Fugees. But unlike that trio’s, the Roots’ first three albums didn’t sell terribly well, so the stakes were high, at least in Questlove’s hyperactive, hypercritical mind, for their fourth, Things Fall Apart, which went on sale the same week as those Grammy Awards.

The mention by Lauryn Hill that night must have been an anointing, because Things Fall Apart finally got the Roots an undeniable hit song, the slinky “You Got Me,” featuring Erykah Badu singing the chorus hook. (It won a Grammy the following year.) Questlove was always restrained on record, keeping his snare and hi-hats pinched to mimic clipped drum-machine tones, but he stretched out and played a skittering solo across the extended “You Got Me” outro on the album version. Did I mention that he wore his hair in a huge Afro and cast a longer, wider shadow than his bandmates? That he wrote the extensive liner notes for every Roots album? In all respects — visually, musically, intellectually — Questlove was the spokesman and stand-in for the Roots as they entered a new era of success, on their own terms.

And Things Fall Apart was just one of the projects that he had spent the previous few years bringing to fruition. They rolled out continuously as the 20th century transitioned into the 21st, one artful, critically acclaimed rap or soul album after another: the poet-singer Jill Scott’s debut, Common’s Like Water for Chocolate, Erykah Badu’s Mama’s Gun, D’Angelo’s Voodoo — a run capped off by an invitation from Jay-Z, the Roots’ theoretical antithesis as a mega-corporate mainstream pop-rapper, to back him on his 2001 MTV Unplugged performance and album.

In a previous generation, a guy who kept that busy playing drums in recording studios would be strictly a drummer — famed players like Steve Gadd and Jim Keltner took session work and earned their paychecks by knowing how to complement a song and nail a take. But Questlove grew up and started making music in the hip-hop era, when “beat-making” was the key skill, one practiced by producers with samplers and synthetic instruments, not sticks. He was always more involved and enmeshed in his friends’ records than a typical session player. Their music was collectively tagged “neo-soul,” for their obvious debt to classic geniuses from Curtis Mayfield to Prince and their comfort with the production styles and techniques of their ’80s and ’90s heroes, and Questlove was the translator of those very different rhythmic eras, the person who embodied a new kind of balance between organic and mechanized musicianship. He could play classic rap beats on his kit, lead an hours-long jam session, and capably sample his playing and others’.

A quarter century on, you can find this combination of talents in many younger drummers across genres, from pop to experimental jazz. And the most amazing thing about Questlove’s career is that his own achievements since have nearly dwarfed this accomplishment. An in-demand DJ, bandleader for The Tonight Show, Oscar-winning documentarian, podcaster, prolific author of memoir, history, and cookbooks — even more than Dave Grohl, his punk-rock equivalent in many ways, Questlove is a multimedia industry unto himself now. But drums remain at the center of his identity, and he is certainly the most well-known and influential player to carry the instrument across the arbitrary but significant-feeling line between the centuries. He was just Ahmir on that historic night in early 1999, a small piece of a compatriot’s enormous moment, but Questlove would never be so anonymous again.

Born in 1971, he inherited music like a birthright. Questlove’s parents were a husband-and-wife duo who spent years in the industry, notably as a short-lived ’70s funk and soul band called Congress Alley, who recorded one album when Ahmir was just a baby that was sampled on Dr. Dre and Snoop Doggy Dogg’s “Nuthin’ but a ‘G’ Thang” when he was 21.

“I grew up on the road,” he wrote in his 2013 memoir, Mo’ Meta Blues. “I thought that living in a Howard Johnson’s was normal.” He picked up drumsticks for the first time as a toddler and learned that trade while watching hundreds of gigs from the side of the stage. He saw the final golden age of live-band R&B up close as it peaked, dwindled, and faded. Before he was even old enough for school, he was backstage one night when his father called him over to introduce Bernard “Pretty” Purdie, who had just spent three years as Aretha Franklin’s drummer. It was time for a lesson. Mr. Thompson wanted Ahmir to hear Purdie explain “how he keeps food on the table.”

“The two and the four,” said Purdie. Essential advice for any toddler.

His father’s strict religious belief meant that Ahmir had to hide the increasingly explicit pop albums of his adolescence, from Run-DMC to Prince. He was expected to go to a conservatory, not start a rap group with a classmate at his Philadelphia music school, as he did after meeting Tariq Trotter, who had a much tougher background and street-oriented focus. After taking the name Black Thought, Trotter became a stunningly agile wordsmith, whether writing or freestyling. In their earliest days, Ahmir’s role was simply to give him beats to follow.

This was the mid- to late 1980s, hip-hop’s first golden age. One rap album after another established new parameters for the music: Eric B. & Rakim’s Paid in Full and Boogie Down Productions’ By All Means Necessary for street-level storytelling and creative sampling; Public Enemy’s It Takes a Nation of Millions to Hold Us Back for sociopolitical and musical attack; De La Soul’s 3 Feet High and Rising and the Beast­ie Boys’ Paul’s Boutique for anything-goes, goofball utopianism. Just as important, at least as Questlove remembered it, was Stevie Wonder’s 1986 appearance on The Cosby Show, where he demonstrated the voice-capture technology in his Synclavier II, a state-of-the-art sampler and keyboard station. It was the first time that most people Questlove’s age saw the actual equipment in action instead of just hearing its output on records.

As the decade turned, the group with Trotter grew more ambitious as well, encompassing a second MC, a beatboxer, an electric bass, and a Fender Rhodes keyboard. In the early ’90s, rap groups were explicitly plumbing the connection between their music and jazz, notably on A Tribe Called Quest’s The Low End Theory from 1991. The Roots fit perfectly in this intellectualized tradition: They resembled Tribe more than the harder-edge gangster rap of the time, even if Dr. Dre was sampling Questlove’s parents. Nevertheless, no one would mistake Questlove’s drumming for a jazz player’s. The Roots were a hip-hop group, which meant his job was to re-create the effect of a sample-based rhythmic bed. The game was repetition, not improvisation. No big fills, and not even any distracting atmosphere in the drum sound. His job was to reverse-engineer a sampler, to play like a machine that was made to replicate a human timekeeper.

“Distortion to Static,” from their 1995 major-label debut album, Do You Want More?!!!??!, is a case in point. You wouldn’t know that Questlove’s kit has any toms at all. His snare cracks without any vibrations, and his bass drum is tuned low enough to feel speaker-bumping.

Instead of fills, he frequently drops out altogether with the bass, returning on a backbeat to emphasize one of Black Thought’s lines — a live band replicating the effect of a DJ’s fader.

The Roots were making a career out of that re-creative style. Their second “percussionist” was the master beatboxer Rahzel, who made unbelievably realistic scratches and other sound effects with his mouth. But the drummer heard something while touring Europe in late 1996 that reshaped his entire approach. It was just a few grainy clips of a new rap group from Detroit, left on his hotel answering machine by Q-Tip, the MC-maestro in A Tribe Called Quest. The group’s name was Slum Village, the producer was Jay Dee, and Questlove spent his per diem on international phone cards just so he could listen to the whole record. Those grainy, broken-up beats are what set Questlove on the path to Things Fall Apart and beyond. “It was my calling, it was Moses coming to the mountain,” he’d later say.

Keep in mind that by 1997, Questlove had heard enough music for 10 normal listeners’ lifetimes. If you discovered some hidden-gem soul single from the early ’70s, it was a certainty that he already knew it, who wrote it, and which studio it was recorded in. He may have even watched the group in person on a bill with his folks. Somehow, that person heard a few rap beats over the phone while traveling and felt convinced that Jay Dee was “someone to lead us out of the darkness, to take us across the desert.” What could that Detroit DJ have done to convince Questlove he was a messiah?

To answer that, history-conscious Questlove would likely go back to the outer boroughs of New York in the 1970s, when DJ Kool Herc, a Jamaican American man in the South Bronx, became the first party­maker to extend the drum breaks on existing records: Take two copies of James Brown’s “Give It Up or Turnit a Loose” or the Incredible Bongo Band’s “Apache,” put them on adjacent turntables, fade the volume from one to another as their drum breaks play on, and the groove can last as long as you want.

In the golden age when Questlove was in his late adolescence and making his first attempts at what became the Roots, sampling had evolved into an art form tailor-made for encyclopedists like him. The boast in the Bomb Squad’s productions for Public Enemy was their daring combination of a Malcolm X speech and a Slayer guitar on the same record, just like Prince Paul and De La Soul could mash up Otis Redding and Steely Dan and make it all sound like Schoolhouse Rock! Creative connections were the coin of the realm, and this period’s hip-hop artists were just as determined toward mind expansion as rock musicians were in the late 1960s. De La Soul even designed 3 Feet High and Rising in Day-Glo hippie chic.

By the ’90s, the best DJs could use drum machines to craft original beats as complex and affecting as any live drum track while still relentless and referential in the way that only mechanized rhythms and clever sampling can be. Dr. Dre’s The Chronic, which dominated the hip-hop landscape in 1992, was built on a backbone of ’70s drum breaks, especially Clyde Stubblefield’s “Funky Drummer” for James Brown and Bill Withers’s “Kissing My Love,” featuring the great James Gadson.

On another track from that year, Pete Rock & CL Smooth’s “They Reminisce Over You (T.R.O.Y.),” Rock took a stray line of saxophone improvisation from an obscure 1967 jazz record, then built a thumping electronic beat on the E-mu Systems SP-1200, a popular but relatively primitive drum machine. He didn’t just loop a single rhythm; he really played the scratchy bass drum sample (using his finger on the SP’s tiny pads) like a live part, almost improvisatory, throughout the whole track. For tracks like this and others, Pete Rock was a hero to anyone with a sampler or drum machine in this era, including Jay Dee.

And yet when Pete Rock first heard beats by the younger man, he of all people thought, “I am out of a job.”

The trick was Jay Dee’s timing. Rather than making use of the hyperexactness available from their equipment, Jay Dee purposefully shifted his bass a slight bit off from his drums or placed his samples just a hair behind where you’d think they would come in. He unlearned his machines’ perfection and made them feel wobblier, more emotive, more human than anyone had before. For anyone who knew the mechanics of making beats, his accomplishment was mind-blowing. This is why Questlove heard his work and thought Jay Dee, or J Dilla as he soon renamed himself for good, was a before-and-after figure like Jimi Hendrix or Charlie Parker. He reoriented the tools of hip-hop rhythm.

In the summer of 1997, Questlove made his first pilgrimage to Detroit, where he spent a few days with this reclusive mastermind. Dilla was meticulous in every aspect of his living conditions, from his clothes to his studio equipment. That’s how he was able to find this unprecedented level of rhythm-voice synthesis. Slum Village’s Fan-Tas-Tic Vol. 1, the record Questlove heard on his answering machine, was recorded a cappella first, with Dilla adding beats after the fact to match the cadences of his fellow rappers. Watching him work, Questlove saw how Dilla could find a usable sound anywhere, like the time he sampled the low humming feedback from a turn­table and used it as a bass drum tone.

“I went to Dilla University,” Questlove later said. Previously, he’d thought that being a professional musician was a matter of attaining “gospel chops,” the raw musical capability to play in a Black church. But now he wanted to sound like this tumbling, mixed-up funk that this fussy Detroiter specialized in. Questlove and his cohort showed that J Dilla’s influence extended to traditional instrumentalists as well. You could hear it on Things Fall Apart tracks like “Act Too (Love of My Life),” where the backbeat always seems to take just a second longer than it should to arrive. But he explored it most fully and fascinatingly in a record that Questlove has said was the high point of his entire career: D’Angelo’s Voodoo.

D’Angelo had already collaborated with Erykah Badu and Lauryn Hill, and his first album, Brown Sugar, fit squarely in their realm of restrained, hip-hop-inspired R&B. But D’Angelo’s seemingly effortless music took ages to gestate. By the time he met Questlove, years had passed since Brown Sugar, and like the drummer, he was less concerned about completing a new record than he was about finding a new way of communicating with music. He wanted to work with the same breadth of intent as Marvin Gaye or Prince, but in ways that felt modern, not retro. R&B music with J Dilla beats could be the essence he’d been searching for. But it would take a band that was good enough to “unlearn” proper musicianship in the way that Dilla made his machines do.

Questlove desperately wanted to play a role. At a Roots show with D’Angelo in the audience, the drummer subtly changed his playing style and quoted drum parts and fills from Prince records, which he knew would attract the singer’s attention. When they started socializing and visiting the studio together, the band filled out with keyboardist James Poyser from the Roots and British session bassist Pino Palladino. J Dilla was in the room most of the time as well, not as a contributor but as a kind of oracle.

The album sessions took years, developing through endless late-night jams at Electric Lady Studios, Hendrix’s Manhattan fortress. They were working out new grooves, like any band in search of a shared language, and their “North Stars” were Prince and J Dilla. Prince was of course a wizard with acoustic and electronic drums in any combination, but his steady robotic funk was the exact opposite of Dilla’s artful sloppiness, and D’Angelo wanted a live band that could play both. Questlove and Palladino worked hard to separate the bass and drums like Dilla could, which is harder than it sounds. Musicians typically look for a shared beat, not a means of lagging behind one another on purpose.

When Voodoo finally came out in early 2000, it was recognized as a major statement, won two Grammys, and turned D’Angelo into a star, especially after his nude appearance in the video for the incredible single “Untitled (How Does It Feel).” Questlove, always happy to explain his artistic intentions, wrote that the record was reflective of the group’s “love for the dead state of Black music, a love to show [their] idols how much they taught [them],” and listed Slum Village among their ancestors.

Voodoo was the first time that live musicians made use of J Dilla’s rhythmic innovations. There have been Dilla-inspired jazz groups and orchestral compositions since, but Questlove brought that approach furthest, all the way to the pop realm. After J Dilla died in 2006 of a rare blood disorder, at age 32, his legend only grew, and now Questlove carries his old friend’s legacy in multiple ways — as a constant presence in the books and films about him, and with his sticks.

The Roots’ masterpiece, at least in my eyes, is their 2002 album Phrenology, which covers a huge range of styles from hardcore punk to sound collages and club rap. Right before they released it, I saw them on that summer’s Smokin’ Grooves tour, between Outkast and Lauryn Hill, and they brought out the singer Cody ChesnuTT to play “The Seed (2.0),” which no one in the audience had heard before. I nearly levitated. On record, the song’s particular mix of strutting soul and hip-hop attitude remains the most vibrant, natural rap-rock hybrid I’ve ever heard. Questlove’s drums boom like Led Zeppelin’s John Bonham busting out of a broken boom box. It’s real chicken-grease rock and roll, and Black Thought’s propulsive cadences only heighten it.

That has been Questlove’s role in popular music ever since that moment of ascendancy alongside the Roots, D’Angelo, Common, J Dilla, and his other fellow travelers. He carries on a tradition of old-school showbiz musicianship while maintaining a contemporary sense of how music is actually made today, and the many possible ways it can be made. He coaxed Al Green back into the studio and produced the legend’s album Lay It Down in 2008, also playing drums.

“I told them to go … put all the hip-hop moves in there,” Green said at the time. “And the more they tried to play it hip-hop, the more they sounded like the first stuff [I’d] been cutting … in 1973, ’74, ’75.” An older artist works with Questlove to get a contemporary sound, but Questlove can’t help but play to the sound he knows from the past. The eternal search for that balance is what defines Questlove, no matter what medium he is working in.

When the Roots became the house band for Late Night with Jimmy Fallon and, later, The Tonight Show, they recorded their next few albums in their dressing room using home studio equipment. The show itself introduced them to a world of new collaborators, one of whom, Elvis Costello, felt instantly like a kindred spirit. No wonder: Like Questlove, Costello grew up the son of a professional musician (in London and Liverpool, not Philadelphia), seeing gigs up close before he could walk, and later became a scholar and performer of multiple musical traditions as well. They produced a full LP together, Wise Up Ghost, in 2013, a collaboration that no one would have expected from the Roots (or Costello) in their respective early careers.

The Roots are one of the last 20th-century rap groups left, but they’ve outlasted many rock bands of their vintage as well, which only underlines that classic hip-hop, like the rock and soul that literally provided so many of its rhythms, is throwback music now. There are still rock bands, of course, new ones all the time, but guitar-bass-drums is just one of many possible ways that a young person might think to make music today, and even if they choose it, a computer will likely be involved on some level too. Questlove set a precedent for how to navigate that relationship between old and new, real and synthetic. Any musician with a backbeat walks that same terrain now, carrying rock and roll, this immortal mutant genre, into the future it always finds.

Published as “Beat Poet” in the November 2025 issue of Philadelphia magazine.