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Questlove's parents enrolled him at the Philadelphia High School for the Creative and Performing Arts.
By the time he graduated, he had founded a band called The Square Roots (later dropping the word "square") with his friend Tariq Trotter (Black Thought).
In 2005, Questlove appeared along with such luminaries as Madonna, Iggy Pop, Bootsy Collins, and Little Richard in a television commercial for the Motorola ROKR phone.
Questlove also appears for a short clip in the 2005 film, The Longest Yard.
on a new version of "All My Rowdy Friends Are Coming Over Tonight" for the season premiere (and formal ESPN debut) of Monday Night Football.
With the exception of The Fugees and Jill Scott, Questlove served as the drummer at the 2004 Brooklyn street concert and was the musical director for the entire show.
Questlove was given an Esky for Best Scribe in Esquire magazine's 2006 Esky Music Awards in the April issue.
It was the last known slave ship to carry slaves to the United States.
Questlove is the only guest to have appeared on Gates's program to be descended from slaves known by name, ship, and where they came from in Africa.