Sunday, December 7, 2025

Thomas Middleditch Gets a Movie Role Right Up His Alley Six Years After Announcing He Was a “Swinger” and Pretty Much Losing His Career

Share

Remember the HBO series “Silicon Valley”?

Thomas Middleditch was one of the stars and looked like he’d cross over to bigger things.

But then he gave an interview to Playboy in 2019 announcing he and his wife were “swinging.”

In the interview, Middleditch said: “To be honest, swinging has saved our marriage. We have different speeds, and we argue over it constantly, but it’s better than feeling unheard and alone and that you have to scurry in the shadows. By the way, it’s now called being “part of the lifestyle.” The term swinging is old.”

He was almost immediately written out of a CBS series called “Plan B” and never heard from again. His wife divorced him and got $2.65 million in a settlement.

Since then, Middleditch has occasional one-offs on prime time, and even appeared in a short lived Broadway play.

Now Middleditch is swinging back into action, kind of, in a low rent sex comedy from success-challenged Vertical Pictures. It’s called “Messy,” and it’s about “a promiscuous love addict who moves to New York City following a tough breakup and sets out on a string of dates in the hopes of finding the right match.”

Sounds about right.

The star and director is Alexi Wasser, whose father the late Julian Wasser, was a famous Hollywood photographer of rock stars and artists. His legendary shot of writer Eve Babitz, naked, playing chess with artist Marcel Duchamp, is one for the records. Julian Wasser was also the photographer who shot pictures of Robert F. Kennedy moments before he was assassinated.

“Messy” also stars Jack Kilmer, Ruby McCollister, Adam Goldberg, Mario Cantone, Ione Skye and Merlot (not Chablis). It will start playing on video on demand and streaming services on Halloween.

PS Playboy has since deleted the full interview, but if you search around you can probably read the rest of.

Donate to Showbiz411.com

Showbiz411 is now in its 13th year of providing breaking and exclusive entertainment news. This is an independent site, unlike the many Hollywood trades that are owned by one company. To continue providing news that takes a fresh look at what's going on in movies, music, theater, etc, advertising is our basis. Reader donations would be greatly appreciated, too. They are just another facet of keeping fact based journalism alive.
Thank you


Roger Friedman
Roger Friedmanhttps://www.showbiz411.com
Roger Friedman began his Showbiz411 column in April 2009 after 10 years with Fox News, where he created the Fox411 column. His movie reviews are carried by Rotten Tomatoes, and he is a member of both the movie and TV branches of the Critics Choice Awards. His articles have appeared in dozens of publications over the years including New York Magazine, where he wrote the Intelligencer column in the mid 90s and covered the OJ Simpson trial, and Fox News (when it wasn't so crazy) where he covered Michael Jackson. He is also the writer and co-producer of "Only the Strong Survive," a selection of the Cannes, Sundance, and Telluride Film festivals, directed by DA Pennebaker and Chris Hegedus.

Read more

In Other News