Club Shay Shay - Miguel Part 1

Visit and use code SHANNON and get $50 in lineups when you play your first $5 lineup! Miguel kicking off global CAOS Tour in February 2026.

Tickets on sale at CAOS album out now Miguel — Grammy Award-winning singer, songwriter, and R&B visionary — joins for a rare, unfiltered conversation on his two-decade journey through music, love, and reinvention. From the early days of Sure Thing to the bold experimentation of his new album CAOS, Miguel opens up about art, heartbreak, and the pursuit of creative freedom.

He reflects on writing Sure Thing after a real-life breakup, how the label tried to give the song to Usher, and what it was like watching it explode again on TikTok over a decade later — charting higher than ever before. Miguel revisits how the industry once told him he was a “hard sell” as a half-Black, half-Mexican artist, and how he turned that rejection into timeless success.

The conversation dives into love, divorce, and letting go — from dating since age 19 to walking away from a marriage in his late 30s. Miguel shares the emotions behind Always Time, the pain of realizing love sometimes means release, and how that experience shaped his growth as a man and artist.

He opens up about what fatherhood means to him, why he protects his child’s privacy online, and whether he’d ever get married again. Miguel also breaks down New Martyrs (Ride 4 U) — a protest anthem rooted in compassion and frustration.

He discusses immigration, identity, and growing up in California as a proud Afro-Mexican, exploring how politics and humanity collide in his art. When asked about ICE and deportation, Miguel doesn’t hold back — reflecting on watching hardworking families get torn apart and what unity between Black and Mexican communities really looks like.

He shares stories of collaborating with some of music’s biggest names: Beyoncé, Alicia Keys, Kendrick Lamar, J. Cole, Travis Scott, and Mariah Carey.

From crafting “Rocket” with Beyoncé to recording in Jamaica with Alicia, Miguel reveals what it’s like creating alongside icons while staying grounded in his own vision. He even opens up about performing with Jamie Foxx, singing karaoke with Rihanna, and the energy of sharing stages with Drake and Future.

Miguel talks money, ownership, and the business side of music — from learning about publishing and royalties to why streaming both empowers and exploits artists. He shares his smartest financial lessons, the importance of owning your masters, and what he’d tell new artists navigating fame in the streaming era.

The conversation gets personal and philosophical too — touching on cancel culture, conspiracy theories, and his viral art stunt that left hooks pierced through his back. Miguel explains what drove him to take that risk, what it symbolized about pain and transcendence, and how he’s learned to embrace discomfort as part of his artistic evolution.

At 40, Miguel is stepping into a new chapter. He reflects on being a Scorpio, on patience, on finding peace, and on the balance between chaos and clarity that defines CAOS.

With honesty and humor, he toasts to love, fatherhood, and the next decade of fearless creation. See for privacy information.