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 (9:00) to a cold pitch backstage at The Tonight Show (10:30) to releasing the film last year (12:30). He also explains the cultural significance of the Harlem Cultural Festival of 1969 (15:39), the indescribable warmth of analogue sound (17:11), and why B.B. King's Why I Sing the Blues endures (18:03).

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 (19:56), Stevie Wonder and Curtis Mayfield at age 2, performing in a traveling band with his parents (23:35), before eventually creating The Roots (28:35).

With distance, Questlove reflects on the group's European excursion (34:34), the infamous Philadelphia jam sessions that placed The Roots in a larger, cultural context (39:30), how his definition of success has evolved with age (41:17), and the profound final words of his manager Richard Nichols (44:12). To close, we sit with the words of Nina Simone (48:43) and how they've inspired Questlove to preserve and restore the history of Black music for future generations (51:36).

To submit a question, comment, or reflection for our mailbag episode, write us at [email protected].

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

See omnystudio.com/listener for privacy information.