Pivots define Lady Wray's career. As Nicole Wray, the Virginia native struck gold with the hit "Make It Hot" in the late 1990s alongside Missy Elliott and Timbaland. In the 2000s, she patiently waited her turn with the Roc-A-Fella family, only to witness the death of a dynasty. However, in the last decade, Lady Wray has found a new runway and is making the best music of her career alongside Leon Michaels and the Big Crown family. In a conversation with Questlove, Lady Wray revisits her journey. She speaks about her pivots and transformation into an introspective songwriter, how the Black Keys helped her channel a new groove, and her joyful performance on Cover Girl.

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Hip hop icon and R&B hitmaker, Jermaine Dupri, tells 30 years of industry tales from Fresh Fest days to career-reviving remixes.

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In this special, live-recorded conversation, Questlove sits down with bestselling author and podcast host Malcolm Gladwell at the iHeart Cafe in Cannes, France. The two old friends embark on a wide-ranging, insightful, and humorous discussion that covers everything from Malcolm’s childhood musical experiences, his theory of creativity and genius, and failing as a pathway to success. Through stories of growing up in a multicultural household, creative serendipity, and collaborative critique, Malcolm and Questlove explore how formative experiences shape both art and perspective. They also reflect on the legacy of critical thinking, the modern media landscape, and the impact of AI on truth and storytelling.

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The legendary Queen of Percussion Sheila E. talks about the secrets of her craft, sneaking her brother into Marvin Gaye's band, having Michael Jackson on speed dial and lessons learned from working with Prince.

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Comedian, author, and fellow podcast host Chelsea Handler joins Questlove for a candid, laugh-filled conversation about her unconventional daily routines, family stories, her love of travel, and the art of living in the moment. Chelsea opens up about finding humor in chaos, navigating relationships, embracing failure, and the importance of taking extended vacations. She shares wisdom, wit, and unforgettable personal anecdotes throughout the episode. Don’t miss this inspiring episode packed with laughs and wisdom. Chelsea's High & Mighty Tour will run throughout early 2026.

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Some might say she’s just an actress but Gabrielle Union has really managed to do it all. She gets real with Team Supreme about Being Mary Jane and a sexual assault activist, the star of Bring It On and a new author—not to mention a new mom!

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The Questlove Show sits down with acclaimed cinematographer Autumn Durald Arkapaw for an in-depth conversation on filmmaking, visual storytelling, and creative purpose. Autumn traces her path from photography to shaping films like Sinners, Black Panther: Wakanda Forever, and The Last Showgirl, while reflecting on how family, heritage, and collaborations with Ryan Coogler and Spike Jonze have influenced her style. She breaks down the importance of trust on set, building meaningful partnerships, and inspiring the next generation. Go behind the camera with one of today’s most visionary creators.

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Hall of Fame guitarist, singer and songwriter Steve Miller joins Questlove Supreme to talk about the early lessons he learned from Les Paul and T Bone Walker, sitting in on an impromptu recording session with The Beatles and performing with greats like Chuck Berry, Sly Stone, and more. This episode first ran in January of 2018.

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