Damon's an intelligent, well-spoken guy, as he demonstrates in many interviews (especially this one re: teachers). Naturally, he plays plenty of intelligent, well-spoken characters, as well as action heroes. So when he shows up leading a comedy it's always a nice surprise, but sometimes he really surprises, showing up in movies or on TV shows you had no idea would involve even a hint of Damon.
Even better than knowing Damon will pop up in a film is when you don't. Those awesome surprise cameo moments (usually comedic) that happen in movies that make you go "no way, was that?!" Yes it was. It was Matt Damon. And he was awesome. These are the very best Matt Damon cameo, so vote up your favorite (usually uncredited) appearance below.
This was in a time when Damon had both the Ocean's and Bourne franchises up and running. Basically, he was one of the movie stars. Him popping up in a teen sex comedy was already surprising, but that he was a nearly unrecognizable tattooed, pierced rocker stealing the hero's girlfriend made this cameo the high point of EuroTrip.
See which starlet almost had a cameo in Matt Damon's lovelife here.
#20 on The Best Party Movies
#35 on The Best College Movies Ever
#27 on The Best Movies for Partiessee more on EuroTrip
In this movie about stopping a movie from being made, Matt Damon and Ben Affleck play themselves...reprising their roles as Will Hunting and Chuckie Sullivan in Good Will Hunting 2: Hunting Season, a creatively bankrupt sequel to their Oscar-winning debut as screenwriters.
Also Rankedsee more on Jay and Silent Bob Strike Back
In a tiny cameo during Chasing Amy, Matt plays Executive #2, a thoroughly '90s cool guy who just doesn't really get it. Damon is friends with both writer-director Kevin Smith and (obviously) the star of the movie, Ben Affleck. Nice to see friends helping friends with movies.
Also Rankedsee more on Chasing Amy
20 people just voted on Entourage
In a running gag throughout the season 6 finale, real life movie star Matt Damon plays Matt Damon, lobbying to convince fictitious movie star Vincent Chase to donate to his charitable cause. "It's for the kids!" The episode actually ends with a weeping Damon.
#13 on The Best HBO Original Seriessee more on Entourage
One of several one-scene appearances in Kevin Smith movies, this uncredited cameo finds Matt Damon simultaneously idolizes and mocks his longtime BFF Ben Affleck.
Also Rankedsee more on Jersey Girl
Most of Finding Forrester is totally devoid of Damon, yet in the final minutes of this drama, the actor appears for a brief but important role that is, in some ways, the emotional lynchpin of the whole movie. This one feels Good Will Hunting director Gus Van Sant called his former leading man in to make sure a scene played just right.
#25 on The Best Movies About Books
#13 on The Best Basketball Moviessee more on Finding Forrester
Ocean's Eleven through Thirteen movies really brought their ridiculous cast together. Not only did Damon cameo in a movie directed by George Clooney, but he also appeared on The Bernie Mac Show, playing himself in a celebrity gold tournament.
#6 on The Best Black Sitcomssee more on The Bernie Mac Show
Another instance of the Ocean's gang sticking together. This time, on Don Cheadle's Showtime series House of Lies, Matt Damon plays a caricature of an egotistical version of himself.