When you think of Matt Damon, your mind likely jumps to Jason Bourne, the Oscar-winning drama of Good Will Hunting, or his recent turn in Oppenheimer. But long before he became an action icon, Damon delivered one of his most delightful performances on a sitcom—a guest spot on Will & Grace that remains a fan favorite and a masterclass in comedic timing.
In 2001, Damon was already a household name thanks to films like The Talented Mr. Ripley and Ocean's Eleven. But his appearance on the hit NBC sitcom, in the episode titled "A Chorus Lie," was a revelation. He played Owen, a straight man so desperate to join the Manhattan Gay Men's Chorus (and score a free trip to Europe) that he pretends to be gay, complete with a fake boyfriend named Ben—a wink to his real-life bestie Ben Affleck.
The episode flips the typical "outed" narrative on its head. Jack McFarland (Sean Hayes) suspects Owen is straight and tries to expose him, but when the truth comes out, the chorus director delivers a hilarious twist: they don't care. "We here at the Chorus have a policy of tolerance," he says, and Owen gets the spot. It's a clever role reversal that celebrates acceptance while poking fun at the absurdity of exclusion.
Damon's performance is pure gold. He commits fully to Owen's fake flamboyance, delivering lines like "All I wanted was to sing and be accepted and maybe dance a little, too" with a straight face that makes it even funnier. The episode, which aired during the show's fourth season, scored an 8.7 on IMDb and remains one of the series' most beloved installments.
This cameo wasn't just a one-off lark. Damon has made a habit of surprising audiences with unexpected appearances, from his brief but memorable turn in EuroTrip (singing "Scotty Doesn't Know") to his scene-stealing Loki in Thor: Ragnarok and his prosthetic-heavy role in Deadpool 2. He's also popped up in 30 Rock and recently made headlines for a walk-on in The Gilded Age.
According to Sean Hayes, the Will & Grace cameo came about after a casual softball game. "We were just playing and I was like, 'Did you want to do the show?' And he was like, 'Yeah, why not?'" Hayes recalled. "Literally it was that easy." Hayes also praised the episode's "smart twist" on the outing trope.
Damon's willingness to poke fun at himself has endeared him to audiences beyond his dramatic roles. Whether he's saving the world as Bourne or pretending to be gay for a singing gig, he brings a charm that's hard to resist. If you haven't seen "A Chorus Lie," it's streaming on Hulu—and it's proof that sometimes the best roles are the ones you least expect.
For more on the sitcoms that defined an era, check out our list of the best sitcoms of the last 30 years. And if you're a fan of Damon's comedic side, you'll want to keep an eye on his upcoming projects, including his new film with Chris Hemsworth.
