In this week’s episode, the crew sits down multi-talented actor and singer Trevor Jackson who opens up about the most personal chapter of his life, the creation of a deeply vulnerable breakup album written during a season of heartbreak, injury, and self-reflection. He talks about crafting the project while recovering from an Achilles tear, why the music poured out of him faster than ever, and how being forced to slow down reshaped him mentally and spiritually.

They get into his journey from tap dancing as a kid in Indiana to Broadway, early record deals, and eventually landing major film and TV roles. He shares the story behind his audition for one of his biggest movies, the long grind of acting, and how certain roles pushed him to grow in ways he wasn’t expecting.

The conversation takes its usual Underground Lounge detours, from sobriety challenges and self-discipline, to wild dating debates, to whether 30 days without sex is even realistic. There’s plenty of honest talk, plenty of jokes, and a real look at how men process heartbreak, growth, and the pressure to keep going.

The episode closes with dreams of future superhero roles, creative reinvention, and the importance of being ready when your moment comes. Authentic, funny, and unexpectedly deep, this one has everything.