For the latest episode of When I Was 17, MTV reached out to ?uestlove to gain more insight into his “roots” as a Philadelphia high school student in 1988-89. After admitting that he was a “band geek,” talking about his role as the lunchtime beat provider and touching on his hippie sense of style that had everyone looking at him,
?uest explains how a Levi’s commercial provided the inspiration responsible for creating his Grammy Award-winning hip-hop band, The Roots. In addition, he relives the disappointing prom night he had with his dream date—who would also go on to be famous—and a talent show in which he and his musical cohort Tariq “Black Thought” Trotter almost beat out one of the biggest R&B groups of all time. The other two celebrities featured in this episode are up-and-coming pop singer-songwriter Christina Perri and the oldest daughter of the Rev Run household, Vanessa Simmons. Watch the video above to take an insightful look back into the earlier years of all three lives.