Matt Damon’s cameo in Confessions of a Dangerous Mind is so blink-and-you’ll-miss-it you’ll still be saying “Wait, was that Brad Pitt?” before you go “Wait, was that also Matt Damon?!”. Damon and Pitt star in George Clooney’s directorial debut as two contestants on The Dating Game, which was basically a ‘70s version of Blind Date. As the camera pans across the pair slowly, pausing on each of them for a fraction of a second, it’s as if Clooney is winking at you through the camera, chuckling “Yeah, that’s who you think it is.” They don’t even have lines!
Why did he do this?: Simple—George Clooney. The pair had just worked together on Steven Soderbergh’s Ocean’s Eleven, kicking off a decades-long collaborative friendship that’s responsible for multiple films and the normalization of movie stars playing pranks on each other.
2. Deadpool 2 (2018)
Matt Damon’s cameo in Deadpool 2 isn’t blink-and-you’ll-miss-it—it’s stare-at-the-screen-the-whole-time-and-have-no-idea-you’re-watching-Matt-Damon. Even looking at the clip now, it’s hard to believe anyone cottoned on to the fact he was in the film at all. The scene introduces Josh Brolin’s villain Cable, who lands on Earth next to two hicks on the back of a pickup truck, having a conversation about toilet paper. Damon is in full hillbilly prosthetics, complete with long hair, beer belly, fake nose and trucker cap, and while he’s soon zapped to death, his Brendan-Fraser-in-The-Whale-worthy transformation is indelible.
Why did he do this?: Presumably as a favor to Deadpool director David Leitch, who worked with Damon on a couple of Bourne films in his former life as a stunt performer.
1. Eurotrip (2004)
In the canon of Matt Damon cameos, there’s no better, more baffling, more bewildering and more beautiful one than his random appearance in the train-based sex comedy Eurotrip. He drops in as the lead singer of a pop-punk band singing about all the ways he boned a girl behind her boyfriend’s back, and from the shaved head to the fake tattoos to the spiked labret chin piercing, it’s about as un-Damon as you can get. By this point he was already Academy Award winner Matt Damon, and you wouldn’t necessarily expect to run into him in a film that involves Xena Warrior Princess sodomizing someone in an Amsterdam sex club and fraternal twins making out. But you sit there and tell us that the way he commits to the lyric “I did her on his birthday” isn’t Oscar-worthy in itself.
Why did he do this?: He was just there. No, literally. He was in Prague filming The Brothers Grimm, and he was college buds with the writers of Eurotrip, who were also making their movie there. So he got the clippers out, and the rest is cinema history.
