The Underground Lounge Podcast brings in comedian and writer Sydney Castillo for an episode packed with laughs, real talk, and the kind of behind-the-scenes stories you won’t hear anywhere else.
From bombing on stage to writing for hit TV shows, Sydney breaks down the wild rollercoaster of comedy and entertainment. He shares how he navigated the Hollywood hustle, the reality of working in writers’ rooms, and the politics that come with making it in the business.
The conversation dives deep into what separates the greats from the rest, the moments that almost derailed his career, and the comedy gems he’s picked up along the way.
Of course, it wouldn’t be an Underground Lounge episode without a few hilarious detours. Sydney recalls some of his most ridiculous encounters, unexpected opportunities, and situations that made him question everything. Whether it’s the struggle of staying relevant, the pressure to always be funny, or the weirdest industry moments he’s experienced, Sydney keeps it 100.
This episode is a perfect mix of comedy, hustle, and Hollywood chaos. If you’ve ever wondered what really goes on behind the scenes of stand-up and TV writing, or if you just need a solid laugh—this one’s for you.
Tune in for nonstop entertainment and insight from one of the sharpest minds in the game!
Sydney Castillo: Originally raised in Fort Worth, Texas, Sydney Castillo is a former winner of TBS’ Funniest Wins and has appeared in 50 Shades of Black, FX’s The League, B.E.T.’s, Real Husband’s of Hollywood. He’s also produced for Bounce TV, B.E.T., and as of recent he wrote an episode and guest-starred on NBC’s sitcom, Marlon. Castillo wrote and appeared on Comedy Central’s Hood Adjacent and #TheRightTime w/ Bomani Jones, Performed stand-up on HBO”s All Def Comedy and Tru TV’s Laff Tracks.
