Sunday, July 5, 2026

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

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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.

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Roger Friedman
Roger Friedman
Roger Friedman is the founder and editor-in-chief of Showbiz411. He wrote the FOX411 column on FoxNews.com from 1999 to 2009, where he covered Michael Jackson, and previously wrote the "Intelligencer" column at New York magazine in the mid-1990s, where he covered the O.J. Simpson trial. He also edited Fame magazine. His bylines have appeared in The New York Times, The Washington Post, the New York Daily News, the New York Post, Vogue, Details, and the Miami Herald. He is a voting member of the Critics Choice Awards (Film and Television branches), and his movie reviews are tracked by Rotten Tomatoes. With D.A. Pennebaker and Chris Hegedus, he co-produced the 2002 documentary "Only the Strong Survive," which screened at Directors' Fortnight at the Cannes Film Festival.

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