The Questlove Show

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 Michels 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.

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.

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.