Poor Matt Damon. Sure, the Oscar winner is one of the most successful actors around, having most recently starred in the Christopher Nolan awards juggernaut Oppenheimer. Conversely, he’s so often the butt of the joke when it comes to his old Ocean’s Eleven buddies George Clooney and Brad Pitt.
The dashing duo has been known to play pranks on the Good Will Hunting star throughout their decades-spanning friendship, especially the notoriously mischievous Clooney, who memorably photobombed his pal while they were promoting their 2017 film Suburbicon in Venice. He even penned a fake “pissed-off” letter from Damon and sent it to comedians Amy Poehler and Tina Fey in response to a joke they made at the Golden Globes.
During the promo tour for his latest directorial project, The Boys in the Boat, Clooney revealed another big prank that he and Pitt played on Damon. In an interview alongside Callum Turner, the subject of People Magazine’s “Sexiest Man Alive” came up—an honor that Clooney has received twice, in 1997 and 2009—which led the actor-director to tell BBC Radio 1‘s film critic Ali Plumb:
Did you know that we did that, Brad and I [campaigned for] Matt? We took out full-page ads in the trades with a picture of Matt Damon in the Speedo that he wore in The Talented Mr. Ripley and said ‘For your consideration for Sexiest Man Alive.’
Clooney chuckled heartily at the memory, but did note that their cheeky move totally worked, as Damon himself was dubbed the “Sexiest Man Alive” by the outlet in 2007. (And like his buddy George, Brad Pitt, too, is a two-time “Sexiest Man Alive” inductee, becoming the first man to earn the title twice in 2000.) Clooney continued:
He became Sexiest Man Alive! He won, yeah!
Callum Turner then tried to ask George Clooney about a prank that Brad Pitt had played against him, but the Ticket to Paradise star jokingly changed the subject with a pointed “Never mind!” We have to wonder if said prank was the same one that Damon said made Clooney the “maddest” he’d ever seen him, when Pitt had forged a letter from Clooney to the crew of Ocean’s 12 telling them to never look the Danny Ocean actor in the eye.
Though it’s usually Damon who’s the subject of Clooney’s practical jokes, the Air actor is seemingly a good sport about it and even was able to poke fun back at his Suburbicon director and his odd pooping habits during the Kennedy Center Honors in 2022:
It has been said that my friend George Clooney is the last of the true movie stars. So, I got to thinking about what exactly that meant. Of course, a number of past Kennedy Center honorees have certainly been movie stars in that classic sense, actors of class and sophistication. Cary Grant, Henry Fonda, Paul Newman, Gregory Peck. And then I think of George, a man who once defecated in Richard Kind’s kitty litter box as a joke. A man who once stole Bill Clinton’s stationery and wrote fake notes to actors about how much the president loved their movies.
We’re not sure when we’ll see fun-loving friends Matt Damon, George Clooney and Brad Pitt together onscreen again, but we’ll at least soon get a big screen reunion between the latter two. Pitt and Clooney will star together in the action-thriller called Wolfs, which comes out this September on the 2024 movie schedule. That means Damon has plenty of time to plan his pranking revenge!