A Questlove timeline from the Roots to Questlove Supreme

By Scott T. Sterling
Photography by Mel D. Cole


In 1987, Ronald Reagan was the president of the United States, Full Metal Jacket was packing movie theaters across the country, and the streets pulsed with the sounds of Public Enemy, Eric B. and Rakim and, depending on where you lived, the Beastie Boys.

It was also the year that Ahmir “Questlove” Thompson and Tariq “Black Thought” Trotter met while attending the Philadelphia High School for the Creative and Performing Arts, starting a musical relationship that still stands almost 30 years later.

Initially dubbing their budding act as Radio Activity, a series of name changes resulted in the duo calling the group Square Roots, before finally settling on the Roots.

From those humble beginnings, the Roots have grown and evolved into hip-hop’s premier live band, and arguably it’s most recognizable: the outfit spends five nights a week as Jimmy Fallon’s house band on the legendary late-night TV series, The Tonight Show.

It’s been a long and winding road for Questlove, who over the years has revealed himself in many forms. Musician, author, historian, foodie, fan, comedian, college professor — the man wears a lot of hats atop his famous Afro.


This is the year that the Roots self-released Organix, the band’s full-length debut recorded live at a concert in Germany. A hot seller at live shows, it spurs a bidding war that finds the outfit signed to DGC Records.


Spending 1994 on the road and in the studio, the Roots emerged at the dawn of the new year with the band’s major label debut, Do You Want More?!!!??!.
Peaking at No. 22 on the Top R&B/Hip-Hop albums chart and No. 104 on the Billboard 200, the inspired full-length generated enough buzz to land the Roots on Lollapalooza’s second stage that summer.


The Roots build on their DGC debut with the expansive Illadelph Halflife, featuring cameos from the likes of Common, Q-Tip and D’Angelo across the album’s 20 tracks. In a pursuit of more radio play, particularly from New York DJ Funkmaster Flex, Questlove took label criticisms personally.
“Somebody said something real dismissive like, ‘Eh, it's probably hard for him to mix Roots music in with regular hip-hop.’ So then all eyes are pointed at me because I don't play with a metronome,” he recalled in a 2010 interview. “So during the whole making of Illadelph Halflife I was trying to sound as much like a drum machine as I could, basically freezing myself creatively for a year.”


This would be a banner period for the Soulquarians, a musical collective including the Roots, Erykah Badu, D’Angelo, Q-Tip and more. Setting up shop in New York’s legendary Electric Ladyland Studios, jam and recording sessions ensued that would result in a series of albums, including D’Angelo’s Voodoo, the Roots’ Things Fall Apart and Erykah Badu’s Mama’s Gun, among others.
“Every day was a new adventure,” Questlove remembered in an interview last year. “I didn’t want to miss any of the magic. Sometimes I would go home and then D’Angelo would call and play me something, and I would be seething with jealousy because I wasn’t there for the magic. I knew instantly that whatever album we were making was going to be a historical moment. I knew it instantly…I’ll say that activity at Electric Lady went full throttle in early 1998.”


The Roots would end the century with the release of the group’s breakout album, Things Fall Apart. Peaking at No. 4 on the Billboard 200, the album was nominated for Best Rap Album at the Grammys (the award would go to Eminem’s The Slim Shady LP). Their single “You Got Me,” featuring Erykah Badu, would take the Grammy for Best Rap Performance by a Duo or Group.
1999 would also see the Roots release a live album, The Roots Come Alive, recorded at various shows around the world.


The Roots appear in the Spike Lee-directed film, Bamboozled.
In the time following the release of the Roots’ Things Fall Apart, Questlove was involved in a plethora of recordings from a diverse range of artists, including N.E.R.D., Fiona Apple and Joshua Redman.
In 2001, Questlove was part of The Philadelphia Experiment, a collaborative album featuring an array of musicians from the city’s vast musical scene, including Christian McBride.


The following year, he’d release a DJ mix, Questlove Presents: Babies Making Babies, with tracks from such artists as Heatwave, Minnie Ripperton and Roy Ayers. 2002 would also find Questlove making an appearance on Christina Aguilera’s Stripped album on the song "Loving Me 4 Me."
For the Roots, it was the year the group would release the album Phrenology, which would take two years to complete. With appearances from Nelly Furtado and Jill Scott, the band expanded its sounds even further, stepping confidently into the world of soulful rock with Cody ChestnuTT on “The Seed (2.0).
“We didn’t set out to make a dark album, we were just basing our stuff on our reality. This is where we are at the moment,” Questlove said of the record’s tone in a 2002 interview. “It’s not just a hip-hop album, which is why it doesn’t come off like that.”


Questlove was a busy man this year, with the Roots finishing and releasing the band’s sixth studio album, The Tipping Point.
It was also the year when he was Jay Z’s music supervisor for a concert at Madison Square Garden. Footage from that live band-driven show would make up a large part of the documentary, Fade to Black.

"People still don't know the infinite possibilities of a band," he said that year. "What's very unfortunate is the Roots are [one of] the only [groups] of black musicians on a major label. That could be seen as an honor, but it baffles me. I don't want to be a novelty. Twenty years ago, groups made records: the Commodores, War, Con Funk Shun, the J.B.'s, Brass Construction. Now if any band were to start, it'd be like, 'Man, they just biting the Roots.' And that's a problem.”


The Roots release the group’s first album on Def Jam Records, Game Theory, which Questlove categorized at the time as “our most serious record to date.” It would peak at No. 9 on the Billboard 200 and earn a Grammy nomination for Best Rap Album (the award would go to Ludacris for Release Therapy).
Questlove played a large role in the movie Dave Chappelle’s Block Party, serving as music director for the massive Brooklyn concert featured in the Michel Gondry-directed film.


The Roots returned this year with a new album, Rising Down, picking up on the socially relevant tone of Game Theory and adding some new dimensions, like the bonus cut -featuring Patrick Stump, “Birthday Girl.” The track comes with a provocative music video starring notorious former adult actress, Sasha Grey.

The Roots launch the band's own annual music festival, the Roots Picnic, in their hometown of Philadelphia. Over the years, the event allows them to jam with a wide range of artists, including Snoop Dogg, Nas, Esperanza Spalding, Usher, and many more.
Questlove and fellow member of the Roots, James Poyser, produce Al Green’s album, Lay It Down.


This was a watershed year for the Roots, as it’s when they were first tapped to serve as the house band on Late Night with Jimmy Fallon. Questlove and the band’s profiles would heighten considerably as a result.
"In the 25 years that the Roots have been together, nobody has disarmed us to that level that quickly, Questlove has said of the relationship with Fallon. “Jimmy just has that personality."


The Roots release How I Got Over, the band’s ninth studio album.
The group would also drop Dilla Joints, a mixtape tribute to late Detroit producer and Soulquarian, J Dilla. They would go on to team up with John Legend for a collaborative full-length, Wake Up! A collection of classic soul song covers, the album was inspired by the 2008 election of President Barack Obama.
Eagle-eyed fans can spot Questlove’s cameo in the 2010 video “Barbra Streisand” from dance music super-group, Duck Sauce.


The Roots embark on another collaborative album, this time with popular ‘70s soul singer Betty Wright, to produce the album Betty Wright: The Movie. The album’s lead single, “Grapes on a Vine,” features Lil Wayne.
Just one month later, the Roots would release concept album Undun, the band’s tenth studio effort.


Another year, another collaborative album from the Roots. With Elvis Costello at the helm, Wise Up Ghost was released on Blue Note Records in the fall. The collection was led by first single, "Walk Us Uptown."
The year would also see the release of Questlove’s memoir, Mo' Meta Blues: The World According to Questlove. In the fall of that year, Questlove releases yet another book: Soul Train: The Music, Dance, and Style of a Generation.

“I'm neurotic about it, but somehow, I managed to read my book,” he explained upon its release. “It's one thing when you write it and email stuff in and they send you the drafts back with corrections and all that stuff. But then I'm reading it and I'm almost at the end. For a few moments, I actually kinda read it third-person. I was like, ‘OK. This guy is interesting.’”


The Roots release the band’s second concept album in a row with their eleventh studio effort, …And Then You Shoot Your Cousin, featuring lead single, "When the People Cheer."
It’s also the year that Jimmy Fallon and the Roots were kicked up to legendary late-night franchise, The Tonight Show.


Questlove is tapped by Pandora to host Questlove Supreme, a three-hour weekly radio show.

In a universe that is littered with larger than life characters, there are few music industry icons that loom as large as Shep Gordon. The subject of actor Michael Myers’ 2014 documentary, Supermensch: The Legend of Shep Gordon, he joined Questlove to talk about his influential career. After being ordained by Jimi Hendrix to wade into the shark-infested waters of music management in the early ‘70s, Gordon would score his first client — then-emerging artist Alice Cooper, who he manages to this day.

Handling a panorama of A-list clients over the years, including Teddy Pendergrass, Anne Murray, Luther Vandross and Rick James, Gordon shared a wealth of incredible stories from the front lines of pop culture, where he existed until the day he abruptly decided to walk away, retire to Hawaii and cook for the likes of the Dali Lama.

Listen to Questlove Supreme live exclusively on Pandora Radio Wednesdays at 10:00 a.m. PST/1:00 p.m. EST


Make sure Gene Simmons has an adequate fruit salad waiting in his hotel room after a show. Never cancel a James Brown show, no matter how sick he is, unless he tells you to do so himself. These are just some of the intimate, behind the scenes stories legendary tour manager, Alan Leeds, shared on this week’s episode of Questlove Supreme.

Starting his music career interviewing James Brown for a college radio station, Leeds would go on to work for the hardest working man in show business for years. D’Angelo, Chris Rock, KISS — Leeds has worked closely with some of pop culture’s biggest icons during their most important moments.

Listen to Questlove Supreme live exclusively on Pandora Radio Wednesdays at 10:00 a.m. PST/1:00 p.m. EST


It was a landmark episode of Questlove Supreme this week as the entire crew made a pilgrimage to Minneapolis for exclusive interviews with Prince’s legendary band, the Revolution.

Wendy and Susannah Melvoin, Lisa Coleman, Brown Mark, Bobby Z., Matt Fink, Dez Dickerson and Andre Cymone were all present to share intimate, hilarious and often poignant stories of their time spent making music and indelible memories with the inimitable Prince Rogers Nelson.

The show is essential for true fans, packed with behind the scenes accounts of private and pivotal moments in Prince’s career, from the time he and the band were booed off the stage while opening for the Rolling Stones in Los Angeles to the inspiration for the song “Starfish and Coffee” — all from people who were there as they happened.

Listen to Questlove Supreme live exclusively on Pandora Radio Wednesdays at 10:00 a.m. PST/1:00 p.m. EST

Few people have had as intimate a relationship with hip-hop’s golden age as Dante Ross. As an integral force behind the scenes of such seminal artists as Queen Latifah and Digital Underground, Ross had a front row seat to the birth of hip-hop through it’s initial breakout as a lifestyle and culture phenomenon. As the esteemed guest on this week’s episode of Questlove Supreme on Pandora Radio, he shared a wealth of memories from his time spent at the vanguard of rap during some of its most important moments. Ross took listeners back to 1989, when he was present with De La Soul while they recorded their groundbreaking debut, 3 Feet High and Rising, through 2000 when he won a Grammy for his work on Santana’s Supernatural, and beyond.

Listen to Questlove Supreme live exclusively on Pandora Radio Wednesdays at 10:00 a.m. PST/1:00 p.m. EST

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