Uploaded June 2026 | Updated September 2026, 1 day ago
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 the unforgettable Ginger Baker milk-and-ulcers story. Christopher Cross is currently on tour [christophercross.com/]
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #ChristopherCross
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 the unforgettable Ginger Baker milk-and-ulcers story. Christopher Cross is currently on tour [christophercross.com/]
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #ChristopherCross
![DJ Cash Money Backstage At The Roots Picnic | Questlove Show
The LEGENDARY DJ Cash Money joins Questlove live from the 2026 Roots Picnic at Philadelphia’s historic Belmont Plateau for a mini masterclass on the city’s turntablism legacy. A renowned turntable wizard, collector, and beacon of Philly Hip-Hop history, Cash traces the city’s evolution from Grandmaster Nell and Cosmic Kev at Hotel Philadelphia to the birth of the Transformer scratch at Central High—breaking down how Philly quietly rewrote the rules of the DJ.
Cash [https://www.instagram.com/therealdjcashmoney/?hl=en] also traces his own evolution from house party selector to technical innovator, inspired by Latin Rascals edits, Gemini mixers, and his own dancer’s sense of rhythm. Along the way, he reveals the wild story behind his “Pump Me Up” routine, which later found its way into Public Enemy’s “Fight the Power” and the Def Comedy Jam theme.
This mini-episode is merely an appetizer for a much bigger discussion to come.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #MaseoofDeLaSoul #VincentMason DJ Cash Money Backstage At The Roots Picnic | Questlove Show](https://i.ytimg.com/vi/mkHUj5V4G4U/mqdefault.jpg)
![Brianna Wiests Cry Song | Questlove Show #shorts
Questlove welcomes bestselling author Brianna Wiest [https://shopcatalog.com/pages/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.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #YoutubePodcast #BriannaWiest Brianna Wiests Cry Song | Questlove Show #shorts](https://i.ytimg.com/vi/myimxkyyNTo/mqdefault.jpg)
![Thundercat on Grief, Mac Miller & Learning to Live in the Present | Questlove Show
The late Reggie Andrews was a Dazz Band affiliate who went on to change countless lives as a music teacher at Locke High School and founder of the Multi-School Jazz Band. Beyond mentoring artists like The Pharcyde and Tyrese Gibson, he shaped a generation of student musicians, including Kamasi Washington, Thundercat, Terrace Martin, and Ronald Bruner Jr. In this clip from The Questlove Show, Thundercat reflects on how Andrews—who died in 2008—transformed lives through mentorship that extended far beyond music and helped cultivate a new Los Angeles Jazz scene.
Thundercats latest album, Distracted [https://thundercat.lnk.to/distracted?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQPOTM2NjE5NzQzMzkyNDU5AAGnF6kOiyKRkGgz1XYTxoW5K1dwQelEMx2iGWcwbUUZi-bs8fhWvbc5MRnqULU_aem_wbuoF6sE8twSG-LkwWrXgA] is out now.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #Thundercat Thundercat on Grief, Mac Miller & Learning to Live in the Present | Questlove Show](https://i.ytimg.com/vi/nFphDTObkU0/mqdefault.jpg)

![Thundercats Obsession with Cartoons, Comics and Anime | Questlove Show #shorts
Thundercat joins Questlove for a wide-ranging, deeply personal conversation that traces his journey from Compton and church gigs to global stages with Flying Lotus, Mac Miller, and beyond. He breaks down the spiritual impact of MF DOOM, how mentors like Dazz Band affiliate Reggie Andrews and his musician parents shaped his ear. Thundercat reflects on surviving LA’s realities, finding creative family with Kamasi Washington and crew, and the role comics, anime, and Disneyland played in building his singular universe. He and Questlove compare Jazz upbringings, talk bass gods (Stanley vs. Jaco), grief and growth after losing collaborators, and the daily work of staying present in a chaotic world. Thundercats newest album, Distracted [https://thundercat.lnk.to/distracted?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQPOTM2NjE5NzQzMzkyNDU5AAGnBl7vlwzb-SkhPTj6L2vbmkDUvUEfWSAHMaQaD7nvMUdPUz26X_a_ID1DGNY_aem_3LU8AfrAG7zohBJeEXg75g], is out now.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #Thundercat Thundercats Obsession with Cartoons, Comics and Anime | Questlove Show #shorts](https://i.ytimg.com/vi/oGZZPsCUT4c/mqdefault.jpg)
![The First Record Joe Kay Bought | Questlove Show
Questlove sits down with Soulection [https://www.soulection.com/] founder Joe Kay live backstage at the 2026 Roots Picnic in Philadelphia. The conversation traces the origins of a global movement that grew from zip files and SoundCloud posts into a worldwide community. Joe reflects on his earliest musical memories—from family deep cuts and white-label promos to discovering J Dilla—and how those influences helped shape the unmistakable Soulection sound.
He and Questlove dig into the craft of DJing, from set architecture and “go-to” records to reading the room and balancing nostalgia with discovery. Joe also explains why he left Los Angeles for Miami in search of a new international energy. Along the way, they explore the role of curators as culture-shapers, the artists Soulection helped amplify—from Brent Faiyaz to Kaytranada—and what it takes to build a movement that still feels fresh 15 years in.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #Joe #JoeKay The First Record Joe Kay Bought | Questlove Show](https://i.ytimg.com/vi/p03xjTgDjIQ/mqdefault.jpg)
![Fab 5 Freddy on the Day MLK Was Killed | Questlove Show #shorts
Hip-hop visionary Fab 5 Freddy joins Questlove for a wide-ranging conversation tracing his journey from Bed-Stuys Hancock Street to the forefront of music, art, television, and culture. While discussing his memoir, Everybodys Fly [https://www.penguinrandomhouse.com/books/775871/everybodys-fly-by-fab-5-freddy-with-mark-rozzo/], Fab reflects on Brooklyns mobile disco scene, the origins of sound system culture, graffitis transformation of subway cars into rolling art galleries, and the experiences that helped shape Hip-Hops foundation. He also revisits the enduring legacy of Wild Style and Yo! MTV Raps, sharing stories about bringing rap to mainstream television, introducing N.W.A to a national audience, directing a classic Snoop Dogg video, and championing groundbreaking artists as an executive. Along the way, Fab shines a light on the unsung heroes of the graffiti movement, recalls encounters with figures ranging from Malcolm X and Thelonious Monk to Jean-Michel Basquiat and Keith Haring, and discusses how art, music, and advocacy continue to drive cultural change today.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #Fab5Freddy Fab 5 Freddy on the Day MLK Was Killed | Questlove Show #shorts](https://i.ytimg.com/vi/p3-g2ZPewrk/mqdefault.jpg)
![Eric Benet on the first wave of Neo Soul | Questlove Show #shorts
Questlove sits down with R&B icon Eric Benét for a deeply human, wildly musical conversation tracing the singer’s journey from Milwaukee family harmonies to gold plaques and Grammy nominations.
Benét opens up about early sonic imprints like Burt Bacharach, Dionne Warwick, and “Wichita Lineman,” his Alabama and Mobile roots, and how discovering Questlove’s own lineage story reshaped the way he thinks about ancestry, Haiti, and spirituality. The two dig into Prince vs. Michael Jackson, a legendary James Brown clip, and what it really meant to grow up in Milwaukee during the Jeffrey Dahmer years.
Benét breaks down his path from band life to major labels, the making and shelving of Better and Better, how David Foster and Dean Parks helped shape Hurricane, and why songs like “Spend My Life With You” and “Sometimes I Cry” never get old on stage. Along the way, the longtime friends talk vocal maintenance, the emotional cost of fame, the rise of Neo-Soul, and what Benét would tell his 16-year-old self. Benéts latest single, Whos Gonna Save Us [https://beacons.ai/ericbenet?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAcGRvZgJleHRuA2FlbQIxMQBzcnRjBmFwcF9pZA85MzY2MTk3NDMzOTI0NTkAAadBTfG-O5rMyVsP-R36A-pStRo315SxYtHyEkkCmN8G13bzJvH5wCJLrwL7pQ_aem_SYobIKfO1tgZRk3TSONinA] is newly available now.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #EricBenét Eric Benet on the first wave of Neo Soul | Questlove Show #shorts](https://i.ytimg.com/vi/pQjbhEmZZn4/mqdefault.jpg)
![The Most Destructive Show Ever w Maseo from De La Soul | Questlove Show
De La Soul’s Maseo sits down with Questlove for an unfiltered deep dive into his Hip-Hop journey, his approach to deejaying, and the making of a true original. From volatile days in Brooklyn and Long Island to early block parties and the creation of classics like “Me Myself and I,” “Afro Connections,” and the epic “Cool Breeze on the Rocks” splice session, Mase breaks down the art, risk, and innovation behind De La’s catalog. He explains how a skipping record sparked a 20-minute freestyle, how an eight-second guitar pedal became his first sampler, and how the same laugh he was once teased about eventually became a defining element of Gorillaz’ “Feel Good Inc.” Plug 3 also opens up about the Nitro Tour, navigating music-industry politics, pioneering De La’s Kickstarter era, and processing the loss of Dave while keeping the group’s legacy alive. De La Souls Cabin In The Sky album [https://linktr.ee/wearedelasoul?utm_s...] is available now.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #MaseoofDeLaSoul #VincentMason The Most Destructive Show Ever w Maseo from De La Soul | Questlove Show](https://i.ytimg.com/vi/pSOX-W3YjO8/mqdefault.jpg)
![I NEVER Do Presets How Joe Kay Navigates a Quick DJ Set | Questlove Show
Questlove sits down with Soulection [https://www.soulection.com/] founder Joe Kay live backstage at the 2026 Roots Picnic in Philadelphia. The conversation traces the origins of a global movement that grew from zip files and SoundCloud posts into a worldwide community. Joe reflects on his earliest musical memories—from family deep cuts and white-label promos to discovering J Dilla—and how those influences helped shape the unmistakable Soulection sound.
He and Questlove dig into the craft of DJing, from set architecture and “go-to” records to reading the room and balancing nostalgia with discovery. Joe also explains why he left Los Angeles for Miami in search of a new international energy. Along the way, they explore the role of curators as culture-shapers, the artists Soulection helped amplify—from Brent Faiyaz to Kaytranada—and what it takes to build a movement that still feels fresh 15 years in.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #Joe #JoeKay I NEVER Do Presets How Joe Kay Navigates a Quick DJ Set | Questlove Show](https://i.ytimg.com/vi/pT_lYc6Rhe8/mqdefault.jpg)
![Vince Staples Idea of Perfect Happiness | The Questlove Show
Vince Staples sits down with Questlove for a rare, unflinching conversation about community, survival, and growing as an artist without losing yourself. Speaking about his latest album, Crybaby [https://bodega.lomavistarecordings.com/collections/vince-staples], Vince shares hard-earned truths and wisdom from his life, cutting through myth and memory with his trademark clarity and dark humor.
The two artists explore happiness, death, faith, hobbies, and the music industry’s shifting gaze on Black artists—while tracing Vince’s journey from riding the bus to Hollywood studios to becoming one of musics sharpest minds.
#TheQuestloveShow #Questlove #TheQuestloveShowPodcast #QuestloveShow #QuestloveSupreme #iHeartPodcasts #iHeart #Podcast #Podcasttolisten #VinceStaple Vince Staples Idea of Perfect Happiness | The Questlove Show](https://i.ytimg.com/vi/pfAm20YQ424/mqdefault.jpg)