While telling that story, Damon revealed that Clooney even pranked his own father, who appears in The Monuments Men, by screening the film for him and adding "In loving memory of Nick Clooney" at the end, because it wouldn't come out for six months and "it's much cheaper to take it off than it is to put in on." Of course, the ultimate prank was just casting them in that 30% Tomatometer score turd of a movie in the first place.
Clooney has repeatedly talked about spending "years" taking out full-page ads of Damon in a green speedo (from Talented Mr. Ripley) with the message "For Your Consideration: Matt Damon for Sexiest Man Alive," making it look like Damon paid for them. Sadly, our long quest to find the legendary ad revealed that Clooney simply tried to take it, but Variety reportedly refused to run it. Still, Clooney told the story in the media so much that it amounted to the same thing, and Damon won in 2007. Perhaps the whole wardrobe stunt was simply Clooney's way to getting his friend's ego back in check after that.