Bachelor #2 in "Confessions of a Dangerous Mind," Miramax Films, 2002

"Confessions of a Dangerous Mind" (2002)

Of the three men George Clooney got to play bachelors on "The Dating Game" for his directorial debut, an adaptation of game show host Chuck Barris' autobiography, only one had not been picked as People Magazine's sexiest man alive. That would be J. Todd Anderson, a storyboard artist for the Coen brothers, who was recruited by Clooney to work behind the scenes until Clooney realized the portly Anderson would be a perfect fit to play the fussy bachelor #3 who wins the bachelorette's heart -- sight unseen -- over the likes of bachelor #1 (Brad Pitt) and bachelor #2 (Damon). As Clooney says during the DVD commentary, "The truth was, in order to ask J. Todd to play the part of the guy that would be laughed about if she ended up with him, I wanted to have two big studs in the other two roles."

Now a prescient precursor to Silverman's ode to cheating on Jimmy Kimmel, Damon's first display of his singing chops came as as Donny, the heavily pierced and tattooed lead singer of a punk band that welcomes the film's protagonist Scott into a party with "Scotty Doesn't Know," a bouncy song detailing the many times and ways he's defiled Scott's girlfriend Fiona. Damon is backed by the real-life band Lustra, comprised of some of his ex-roommates from Harvard, which is also where Damon met "Eurotrip"'s writer/directors Alec Berg, David Mandel and Jeff Schaffer before they were all bound for Hollywood. When the trio discovered that their comedy would be shooting in Prague at the same time as Damon was working nearby on "The Brothers Grimm," they called in a favor.

Continuing his streak of playing #2s, Damon reunited with his "Dogma" director Kevin Smith for a bit of déjà vu. Shortly before he became a household name with "Good Will Hunting," Damon took a minor role in "Chasing Amy" as "Shawn Oran - Executive #2," an MTV producer who tries to lure Holden and Banky (Ben Affleck and Jason Lee) to adapt their comic book for TV. In "Jersey Girl," Lee and Damon sit across from Affleck's Ollie Trinke as PR execs #1 and #2, respectively, who interview Trinke for a job. Smith laments on the DVD commentary, "You don't know how disheartening it is to be at a test screening and get cards back where like 'scene liked most: Jason Lee and Matt Damon' because you're like dude, they were in the movie for a minute."

Damon fulfilled a lifelong dream for Francis Ford Coppola, who admits in the film's DVD commentary that he always longed for a career where he could ask the stars of his bigger movies to show up for a smaller part in one of his personal films, à la Max von Sydow's role as a gas station attendant in Ingmar Bergman's "Wild Strawberries." When Coppola needed to cast the role of an American OSS officer who attempts to recruit Tim Roth's supernaturally gifted Dominic during World War II, he asked himself who would be "quintessentially American"? Soon after, he brought his star from "The Rainmaker" to Romania for a day's shoot. "I didn't want to make a big deal that it was Matt Damon," Coppola says. "But he was just so perfectly American, I couldn't resist."

[Photos: "The Majestic," Warner Bros. Pictures, 2001; "The Third Wheel," Miramax Films, 2002; "Euro Trip," DreamWorks Distribution, 2004; "Jersey Girl," Miramax Films, 2004; "Youth Without Youth," Sony Pictures Classics, 2007]

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Stephen Saito

I realize I’ve been remiss in not mentioning the one time Damon actually played himself in a movie in “Jay and Silent Bob Strike Back,” reprising his role as Will Hunting in “Good Will Hunting 2: Hunting Season,” the film within a film that Kevin Smith’s dynamic duo stumble upon while trespassing on the studio lot. Gus Van Sant literally sits back and counts his money as Damon and Ben Affleck replayed the famous “how ‘bout them apples” scene from the original “Hunting,” but ending with a shotgun rather than fisticuffs. Originally, the film’s plot actually hinged on Damon and Affleck, but their roles diminished as future drafts of the script came in (and as Smith admits on the DVD’s commentary, Damon’s increasingly busy schedule wouldn’t allow it). And despite the presence of Van Sant, Damon and Affleck, what really sells the scene is the return of Scott Winters, who plays the blond ponytailed villain in the Boston pub that once again pesters Damon about Vickers’ “Work in Essex County.” That, and watching Damon and Affleck going through acting exercises before the cameras roll. (The clip is here: http://www.youtube.com/watch?v=MZ70hbvaPdU)

Titus

What about Damon's cameo in Team America: World Police?

Adam

Most recently he has a quick cameo in Che (part 2). That was nice to see, and I think everyone else in the theater appreciated it- it's nice when lesser-known actors are able to get work, no matter how small.

Joe

My favorite Damon cameo was actually on an episode of Law and Order as himself.

The story revolved around a murder suspect who was a failed actor. To get him to crack, they show him the embarrassing dailies of a botched scene he was supposed to do with Matt Damon. While the footage was only of the suspect's coverage, you can hear Damon's voice feed him his line cues.

Sure enough, Damon was credited at the end and the episode is listed on his imdb page.

Ezradams

I think Matt Damon also was playing cards and is seen briefly in The Majestic just after his narration near the end of the film