The wildest stories from the Sunshine State are returning for another round. Season 2 of HBO’s “It’s Florida, Man” premieres on Friday, November 28, 2025. The six-episode season will air weekly on HBO and stream on HBO Max, taking viewers through the holiday season with a new batch of unbelievable true tales from Florida.
The show features real accounts from Floridians, which are then brought to life with comedic reenactments by a star-studded rotating cast. This season’s guest stars include Adam DeVine, Tiffany Haddish, Johnny Knoxville, and Taika Waititi, among many others. The series is a production from Rough House Pictures, the company behind HBO’s “Eastbound & Down” and “The Righteous Gemstones.”
Full Episode Release Schedule
HBO will release one new episode of “It’s Florida, Man” each Friday night. The season kicks off in late November and runs through the start of the new year. Here is the complete release schedule for Season 2.
- Episode 1: “Speedy” – Friday, November 28. A criminal determined to get his dog back plans to steal an entire casino boat. The episode features guest stars Shea Whigham, Johnny Pemberton, and Bert Kreischer.
- Episode 2: “Pizza Man” – Friday, December 5. After a night of partying, a man from Pensacola wakes up almost naked in a pizza restaurant. This story stars Adam DeVine, Nick Swardson, and Chet Hanks.
- Episode 3: “Cuckoo Girl” – Friday, December 12. A woman from Naples has a bad reaction to a new medication and ends up in trouble with the law. The episode features Edi Patterson and Tiffany Haddish.
- Episode 4: “Bigfoot” – Friday, December 19. A man from Sarasota ventures into the Everglades with a new friend to search for the elusive Skunk Ape, Florida’s version of Bigfoot. It stars Haley Joel Osment and Milan Carter.
- Episode 5: “Moonshine” – Friday, December 26. An opportunist trying to make money as a moonshiner stumbles into a turf war. This episode stars Nick Thune and Johnny Knoxville.
- Episode 6: “Crushed” – Friday, January 2. A sheltered teenager from Jacksonville travels to Orlando to meet her online goth prince and nearly becomes a cautionary tale. The finale features Joel Kim Booster, Taika Waititi, and Rita Ora.
About the Show and Its Cast
“It’s Florida, Man” is a late-night comedy series that celebrates the unique and often bizarre character of Florida. The show is described as “a love letter to the beaches, backwaters and basements of a misunderstood yet magical state.” Each episode presents candid interviews with real Floridians who lived through these extraordinary events, paired with playful recreations by a rotating ensemble of actors and comedians.
The charm of the series lies in its storytelling style, where the real people share their experiences with enough heart to remind you these are real events. The show’s producers have stated that the story selection process is long because they seek out people and stories that first make you think the person is insane, but by the end, make you question who the crazy one really is.
The list of guest stars for Season 2 is extensive. In addition to those already mentioned, the season will feature Edi Patterson, Haley Joel Osment, Bert Kreischer, Nick Swardson, Shea Whigham, Rita Ora, David Koechner, Chet Hanks, Milan Carter, Nick Thune, Swoozie Kurtz, and many more.
How to Watch
New episodes of “It’s Florida, Man” Season 2 will air on the HBO cable channel on Fridays at 10:00 p.m. ET/PT. Each new episode will also be available to stream on HBO Max on the same Friday evening it premieres on linear TV. Unlike binge-style releases, the show will follow a weekly rollout, with the season finale arriving on January 2, 2026.
Season 2 is created and executive produced by Mark Herwick for Range Studios and Jeff Tomsic, who also directs. Executive producers Danny McBride and Brandon James return for Rough House Pictures.
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