Christopher Cross joins Questlove in Hollywood for a deep musician-to-musician conversation about songwriting, studio craftsmanship, and surviving meteoric success. Cross reveals the true origin of Arthur's Theme (Best That You Can Do) and the outlaw mythology behind Ride Like The Wind, while recalling experiences like seeing Jimi Hendrix live, opening for Led Zeppelin, and singing background vocals with Carl Wilson. He breaks down the making of his classic debut album, his obsession with Steely Dan–level precision, and why his later records still matter deeply to him and his core fans. Along the way, Cross shares rare stories about Brian Wilson, Joni Mitchell, Michael McDonald, and Jimmy Page — plus an unforgettable Ginger Baker milk-and-ulcers story.

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In a recent conversation with Padma Lakshmi, Questlove brought up the near-sacrilegious act of putting ketchup on a hot dog in Chicago. Chicago native Open Mike Eagle reacts — while admitting he may already be disqualified from the debate for entirely different reasons. The podcast affiliate (and recent guest) also speaks about the hometown food he gravitates towards, name-checking some purveyors. 

The mini episode conversation with Mike and show producer Cousin Jake also veers into touring life, road food, and experiences traveling through Europe.

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Angela Nissel joins Questlove for a deeply funny and moving conversation about growing up in Southwest Philly, breaking into television, and navigating grief after losing her mother—the subject of her new memoir, Good Grief, Pass The Bread, Mom Is Dead.

The longtime friends revisit their wild early days together, from telemarketing gigs and busted cars to building Okayplayer and discovering the early internet, while unpacking people-pleasing, therapy, and late-in-life self-discovery. Angela opens up about caregiving, moving her mother to Los Angeles, surviving Hollywood burnout, and rediscovering who she is beyond work—all with the sharp wit that helped shape shows like Scrubs and The Boondocks.

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In this Questlove Show mini-episode, Questlove revisits the making of Michael Jackson's HIStory with a previously unreleased encore segment from the Jimmy Jam & Terry Lewis interview. Ahmir unpacks the track’s orchestral scale, Boyz II Men vocals, and marathon mix sessions with fellow producers, breaking down why “HIStory” feels like MJ’s “Night of the Living Baseheads” moment.

From there, the conversation pivots to mailbag questions from podcast supporters about Jam & Lewis’ creative synergy, Prince deep cuts, and Questlove’s new Rolling Stone feature ranking 100 essential Prince songs.

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On this mini episode of The Questlove Show, Open Mike Eagle and Cousin Jake react to the recent two-hour interview between Ahmir and Posdnuos. In a mutual celebration of the Native Tongues movement, they highlight moments from the conversation involving De La Soul’s Turtles lawsuit, newly revealed details about subliminal lyrics, and the emotional weight of songs like “I Am I Be” and “Trying People,” connecting them to themes of vulnerability and longevity in Hip-Hop. Make sure you've heard the original April episode.

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Raheem DeVaughn joins Questlove to trace his journey from a Washington DC Go-Go kid to internationally known “Love King,” radio host, and independent R&B force. He breaks down the spiritual meaning of love, the art of the perfect slow-jam mixtape, and how Go-Go culture shaped his sound and hustle (including his current band). Raheem also tells stories about his father touring with Stevie Wonder, remaking a full, soon to release Marvin Gaye album with Kenny Dope, and building his career from Black Lily open mics to a Jive Records deal and beyond. He also explains how he inherited The Quiet Storm radio show, why direct-to-consumer is changing the game, and what it really takes to survive as an indie artist in today’s music industry.

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Questlove welcomes bestselling author Brianna Wiest (The Mountain Is You, 101 Essays That Will Change The Way You Think) for a vulnerable, funny, and wide‑ranging conversation about self‑sabotage, creativity, and learning to “just show up.” Brianna explains how she writes from her center, why nature and long drives unlock her best ideas, and how she separates the heart’s “what” from the mind’s “how.” Questlove shares how her work helped him see himself (and his obstacles) differently. Along the way, Brianna opens up about her childhood, her taste in music, and even making wedding cakes. This episode is a warm, insightful exploration of growth, bravery, and redefining success in the second act of life.

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Questlove reconnects with Open Mike Eagle, picking up a conversation that began on a 2025 episode of the show. As Mike reflects on his time with Project Blowed, the two artists-turned-podcast hosts dive into The Good Life Cafe and its influence on the West Coast Underground Hip-Hop scene, as well as touring on the left side of the country.

This mini-episode is entertaining and insightful—and leaves plenty more of Mike’s story still to be told.

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Posdnuos of De La Soul sits down with Questlove for a long-awaited conversation fans have been asking for. Ahmir digs into the group's catalog with fan-driven questions, while Plug 1 shares stories from the studio, reveals which classic tracks were originally intended for other artists, and reflects on the legacy of his brother, Dave aka Trugoy the Dove. The discussion celebrates one of Hip-Hop's most influential groups—and their lasting impact on The Roots. With last year's Cabin In The Sky album still in constant rotation, this is an episode fans won't want to miss. Catch De La Soul at May's Roots Picnic in Philadelphia.

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This segment from the Questlove Show was so powerful, we had to share it on its own.

Georgia Anne Muldrow breaks down the deeply personal origins of her “Stay Woke” lyric from Erykah Badu’s “Master Teacher Medley" over 18 years ago, and reflects on how its meaning has evolved—and been distorted—over time.

Questlove and special guest Open Mike Eagle share their reactions to her story. Please make sure you've heard the nearly two hour conversation between Georgia and Ahmir that published earlier this week.

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