Questlove’s first gig came at the age of 13, during a performance at Radio City Music Hall. That same year, Thompson was named the musical director for his father’s group, and he became determined to establish his own career in music.

His parents additionally fostered their son’s musical talents by enrolling him in the Philadelphia High School for Creative and Performing Arts in the mid 1980s. It was there that Thompson befriended classmate Tariq Trotter, an aspiring MC. Thompson, performing under the name "Questlove," and Trotter, taking on the moniker "Black Thought," began performing around Philadelphia as The Square Roots in 1987; unable to afford expensive DJ equipment, Trotter simply rhymed over Thompson's drumbeats.

The pair gradually moved from street performances to gigs at local clubs, earning them critical acclaim and underground credibility. Together, Questlove and Black Thought helped to develop a new musical movement, later recognized as neo-soul.

Today, Questlove is best known as the drummer and joint frontman (with Black Thought) for the Grammy Award-winning band The Roots, which is now the in-house band for Late Night with Jimmy Fallon. He has produced for artists including Elvis Costello, Common, D'Angelo, Jill Scott, Erykah Badu, Bilal, Jay-Z, Nikka Costa and more recently, Al Green, Amy Winehouse and John Legend. He is a member of the production teams the Soulquarians, The Randy Watson Experience, The Soultronics and The Grand Wizzards.

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