Complete cast breakdown of It's Florida, Man season 2: Who plays Who & where you’ve seen them before

A crazy, absurd, or surreal situation that could only (or stereotypically) happen in Florida has returned to the screen with It’s Florida, Man season 2. Consisting of just six episodes, the show will roll out new episodes weekly on every Friday. The first episode, "Speedy," was released on November 28, 2025, at 10 p.m. ET/7 p.m. PT on HBO and HBO Max.

Rather than a traditional serialized drama/comedy, the show works as an anthology-style/sketch-style series: each episode presents a self-contained story, a different scenario, and various characters rotating each episode, all revolving around that trademark “Florida weirdness.” The show will conclude its second season with its sixth and last episode on January 2, 2025. The series is created by Mark Herwick and Jeff Tomsic, with executive producers Danny McBride and Brandon James from Rough House Pictures.

The official synopsis of It’s Florida, Man season 2 reads: 

“From Rough House Pictures (HBO’s “Eastbound & Down” and “The Righteous Gemstones”) and Range Studios, this outrageous late-night comedy series brings to life unbelievable ripped-from-the-headlines tales of the Sunshine State – straight from the people who live there. Featuring candid accounts from everyday Floridians playfully recreated by a rotating cast of actors and comedians, this hilarious and irreverent series sheds light on the viral, wacky, and weird. With equal parts humor and heart, IT’S FLORIDA, MAN. is a love letter to the beaches, backwaters, and basements of a misunderstood yet magical state.”

The cast and comedians change for every episode, so there are no specific details about which actor will play which role. However, a list of confirmed guest stars to appear in It’s Florida, Man season 2 has been announced, and this article explores all about them.

Meet the cast of It’s Florida, Man season 2

According to reports by Warner Bros. Discovery (press release), in the first episode of It’s Florida, Man season 2, Shea Whigham, Johnny Pemberton, Bert Kreischer, Brian Sacca, Hassie Harrison, Joseph Rudda and Michael McDonald were confirmed to make their appearance. 

For episode 2: Adam DeVine, Nick Swardson, Chet Hanks, and Olivia Taylor Dudley.

For episode 3: Edi Patterson, Tiffany Haddish and Swoosie Kurtz.

For episode 4: Haley Joel Osment and Milan Carter.
 
For episode 5: Nick Thune, Johnny Knoxville and Ryan Mirvis.

For episode 6: Holmes, Joel Kim Booster, Frankie Quiñones, Ping Wu, Taika Waititi and Rita Ora.

Since their roles are likely on-off and differ across episodes, there is no credible database that enumerates all character names and matches them with actors.

Here’s a list of a few actors from It’s Florida, Man season 2, and where you must have seen them before

Adam DeVine has appeared in many comedy shows. He played Adam DeMamp in Workaholics, Andy in Modern Family, and also acted in musical films like Pitch Perfect and Pitch Perfect: Bumper in Berlin.

Tiffany Haddish is known for her voice role in The LEGO Movie 2 and has starred in Girls Trip, The Last O.G. and The Carmichael Show.

Haley Joel Osment is known for his roles in The Sixth Sense, A.I. Artificial Intelligence, and Pay It Forward. He was also previously seen as Forrest Jr. in Forrest Gump (the son at the end of the film), Tusk, Sex Ed and voiced Kash D. Langford on the Netflix series Jurassic World Camp Cretaceous (2021). 

Johnny Knoxville is the fearless prankster and stunt performer from the Jackass franchise. He has also acted in several films, including Bad Grandpa, The Ringer, The Dukes of Hazzard and Men in Black II.

Taika Waititi is an actor and director who has appeared in films like Jojo Rabbit, where he played an imaginary version of Hitler. Alongside acting, he has directed and written acclaimed films like Hunt for the Wilderpeople, What We Do in the Shadows and Jojo Rabbit.

Other confirmed guest actors in It’s Florida, Man season 2 are: 

Edi Patterson, Bert Kreischer, Nick Swardson, Shea Whigham, Rita Ora, Holmes, David Koechner, Joel Kim Booster, Chet Hanks, Milan Carter, Nick Thune, Swoozie Kurtz, Johnny Pemberton, Ryan Mirvis, Brian Sacca, Ping Wu, Olivia Taylor Dudley, Frankie Quiñones, Hassie Harrison, Joseph Ruud and Michael McDonald.