“I want to note how important dreaming is. I absolutely grab people by the collar and insist, implore them: daydream moreSummer of Soul was the first time that I actually had a fantasy or dream for something, and it happened beyond my wildest imagination. I think dreams are important, and we need to dream more.”

-Questlove, episode 259 of Talk Easy with Sam Fragoso

This week we sit with legendary bandleader of The Roots, Questlove! On the heels of his directorial debut, Summer of Soul, 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 mail@talkeasypod.com.

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