What does it actually take to stay relevant for four decades without losing your soul?
Before he was a hip-hop icon, LL Cool J was just a kid riding mini bikes and dreaming big. Decades later, he joins Trevor and Eugene to reflect on the wild journey—sharing unforgettable encounters with Quincy Jones and Michael Jackson, the family values that kept him grounded, and why true reinvention requires dropping your ego. Plus, LL breaks down why intuition is God’s voice, why cynicism is just cowardice in disguise, and how he turned his grandfather’s belief into his legendary debut album, Radio.
Oct 1
1 hr 58 min
What makes a joke work, and why are we so afraid to have real conversations? British comedian Jimmy Carr joins Trevor and Eugene to break down the mechanics of comedy, the rise of AI, and what we’re losing as human connection becomes harder to find. Jimmy shares how making his depressed mother laugh helped launch his career, what writing a book about the structure of jokes taught him about being funny, and why dark humor can help us confront the things that scare us most. It’s a funny, surprisingly vulnerable conversation about comedy, technology, and why making each other laugh may be one of the most human things we do.
Sep 24
2 hr 16 min
Colin Kaepernick tells the parts he's never told: what NFL owners said in the room, the offer made while he was being blackballed — and the Jay-Z call that never happened.
In this episode of What Now?, Colin sits with Trevor and Eugene for the full story: adopted into a white family in Turlock, the hair that became an identity, the backup who took a team to the Super Bowl in his 10th start — and the protest that cost him everything.
Sep 17
2 hr 23 min
Sizwe and Eugene are not letting Trevor get a hair transplant without a fight. What starts as a beard debate spirals into elbow grafts, foreskin logistics, and the exact wingspan-to-height ratio you'd need after leg-lengthening surgery. Trevor makes an unexpectedly convincing case for Elon Musk as pure talent wrapped in pure bamboozlement, and the three rank which movies actually change how you see the world -- plus Trevor's borderline-scientific approach to watching them on a plane. Then it turns real: xenophobia, why nuance doesn't sell, and who a mob actually protects when it picks a target.
Sep 10
1 hr 17 min
Why do your shoes always fly off in a car accident? Trevor, Eugene, and Khaya chase that question straight into Eugene’s own wild motorbike crash story, involving a T-bone, a second accident two days later, and somehow living to tell the tale. From there, the conversation takes its usual unexpected turns, from South African taxi stickers and quick funerals to a rumor involving Stevie Wonder and Nelson Mandela. And the guys take a moment to remember Dolly Parton, reflecting on the music, humor, and humanity that made her so beloved.
Sep 3
1 hr 39 min
Are you constantly overwhelmed by your to-do list? Obsessed with productivity hacks? Always feel like you’re falling behind? Trevor and Eugene sit down with author and journalist Oliver Burkeman to rethink our relationship with time, success, and control. They unpack why perfectionism can make us miserable, the surprising value of “good procrastination,” and why choosing what to fail at might actually be a good thing. Along the way, they explore the psychology behind our social media facades, how modern conveniences have made us less patient, and whether the secret to getting more out of life might be accepting that we can’t do everything.
Aug 27
1 hr 19 min
Does the language you speak shape how you see the world? Cognitive scientist Lera Boroditsky joins Trevor, Eugene, and Dave to explore how our native tongue can influence everything from our personalities to who we blame when things go wrong, and why bilingual people can feel different depending on which language they're speaking. They dive into cultures that navigate using north, south, east, and west instead of left and right, the relationship between language and thought, and why we're all susceptible to the illusion that we're better at communicating than we actually are. It’s a funny, mind-expanding conversation about how the words we use may shape far more of our world than we realize.
Aug 20
1 hr 48 min
Tracee Ellis Ross has spent a lifetime forging an independent identity. She regales Trevor and Eugene with stories of growing up in the embrace of her iconic mother, Diana Ross, building her own beauty empire with Pattern and starring on Broadway. Together, the three candidly dissect the societal pressures women face to be "chosen," the racial biases of '90s television, and how to reclaim your agency in work and love.
Packed to the brim with lessons on life, love, and picking the perfect heirloom tomato, this episode is a masterclass in belonging to yourself.
Aug 13
1 hr 38 min
Wil Sylvince is back, and the conversation goes exactly where you'd expect and nowhere you could predict. Trevor, Eugene, Dave, and Wil bounce from pop culture debates and comedy tangents to a candid conversation about the health journey that changed Wil's life. Along the way, they tackle everything from misheard Rihanna lyrics and the Michael Jackson biopic to awkward relationships, before settling the only debate that really matters: which Michael Jackson songs belong at the very top.
Aug 6
1 hr 53 min
Estee Adoram is a comedy legend. You've never seen her on a stage, but every comedian you love has had to earn her approval. This week, Trevor, Eugene, and Dave sit down with the legendary talent booker of New York City’s famous Comedy Cellar to talk about her four decades discovering comedic talent. Together, they discuss what it takes to spot greatness before anyone else, how the Cellar has maintained its singular reputation, the evolution of stand-up, the line between comedy and a soapbox, and which rising comedians have her attention today.
Jul 30
1 hr 56 min
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