Oscar Sunday with Questlove
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To celebrate Oscar Sunday, we’re returning to our talk with legendary bandleader of The Roots and director of Summer of Soul, Questlove!

We discuss his winding road to making the documentary: from a trip to Japan (7:47) to a cold pitch backstage at The Tonight Show (9:22) to releasing the film last year (11:35). He also explains the cultural significance of the Harlem Cultural Festival of 1969 (14:58), the indescribable warmth of analogue sound (16:40), and why B.B. King’s Why I Sing the Blues endures (16:50).

Then, in the spirit of Summer of Soul, we dive into the musical past of Questlove: listening to Sly & the Family Stone in the bathtub at age six (18:20), Stevie Wonder and Curtis Mayfield at age 2, performing in a traveling band with his parents (23:00), before eventually creating The Roots (27:30).

With distance, Questlove reflects on the group’s European excursion (34:22), the infamous Philadelphia jam sessions that placed The Roots in a larger, cultural context (37:00), how his definition of success has evolved with age (40:40), and the profound final words of his manager Richard Nichols (43:37). To close, we sit with the words of Nina Simone (48:20) and how they’ve inspired Questlove to preserve and restore the history of Black music for future generations (51:32).