The Man Who Would Be Edgar Pudwacker: Matt Damon’s 15 Funniest Appearances

On March 12th, Matt Damon and director Paul Greengrass will be together again in theaters for their latest action thriller, “Green Zone,” a film set in the chaotic early days of the Iraqi War when no one could be trusted and every decision could detonate unforeseen consequences. Damon and Greengrass have clearly proven that they’ve got chemistry, what with their work together on “The Bourne Supremacy” and “The Bourne Ultimatum,” and we’re obviously looking forward to checking it out, but…well, here’s the thing: Damon’s a great action hero, but he can be pretty hilarious, too, and “Green Zone” doesn’t exactly look like what you’d call a laff riot.

Green Zone - Matt Damon

To help cleanse your palate either before or after you’ve seen the film, however, we’ve compiled 15 of our favorite occasions when Matt Damon made with the funny. Your personal mileage may vary, but we’re guessing that, at the very least, you’ll get more laughs out of these clips than you will from “Green Zone.”

(Plus, don’t forget to head over to our “Green Zone” contest, where we’re giving away an Xbox 360!)

1. Glory Daze (1996): Okay, we’ll be honest with you: Damon’s barely in this film. It’s really a vehicle for his longtime buddy, Ben Affleck, who sports some seriously douche-tastic facial hair throughout the film. Although the remarkable number of recognizable faces to be found within the cast make it worth checking out (Sam Rockwell, Alyssa Milano, Matthew McConaughey, John Rhys-Davies, Kristin Bauer, French Stewart, Brendan Fraser, Leah Remini, Meredith Salinger, Mary Woronov, and Spaulding Gray all make appearances), the predominant reason we’ve included “Glory Daze” – which is, for the record, explores the hesitation all college graduates experience before entering the real world – is because no matter how many films he may eventually have to his credit, Matt Damon should never be allowed to escape the fact that, even though it was only for a few fleeting moments, he once played a character named Edward Pudwacker.

2. Dogma (1999): Kevin Smith movies aren’t generally where one goes to find eyebrow-raising theological discourse, but there are moments within this epic comedy that do indeed inspire such a reaction. Here, Damon – playing a fallen angel named Loki – proceeds to take a leisurely stroll through an airport and, in one brief conversation, casually destroy everything this poor nun has ever believed in. Why? “I just love to fuck with the clergy,” he says. “I love to keep those guys on their toes.”

3. Jay and Silent Bob Strike Back (2001): It’s not quite on the level of Buck Henry pitching a sequel to “The Graduate,” but watching Gus Van Sant counting his money as he makes “Good Will Hunting 2: Hunting Season” is still pretty funny.

4. Will and Grace (2002): This is the only inclusion on the list without a clip to accompany it, but we couldn’t very well ignore it. Damon plays Owen, who’s competing against Jack for a spot in the New York Gay Men’s Chorus…except that Owen isn’t gay. He just wants the all-expenses-paid trip to Europe for the summer. Jack’s onto his game, but to get Owen to confirm his heterosexuality, he turns to Grace. The episode is worth it just for Damon’s performance as he tries to figure out a way to get the best of both worlds. “Whoops, my hand seems to be traveling up your thigh towards your rockin’ ass,” he says to Grace. “But who cares, right? ‘Cause I’m gay. So it’s all right if I tell you you’re beautiful, throw you down on this couch, and make out with you fiercely, right?” Riiiiiiight.

5. Stuck On You (2003): For as funny as Damon can be, he’s generally pegged as an action guy nowadays, so it’s nice to be able to look back at his one full-fledged comedy once in awhile. “Stuck on You” may not be the Farrelly Brothers’ best work, but don’t tell me you weren’t at least a little bit curious when you first heard that they were going to be making a movie in which Matt Damon and Greg Kinnear play Siamese twins.

6. Eurotrip (2004): No, it’s not really Damon singing “Scotty Doesn’t Know” – it’s actually a song by the band Lustra, and you can find it on their 2006 album Left for Dead – but that doesn’t make the song’s lyrics any less funny.

7. Jimmy Kimmel Live! (2006): Longtime viewers of this show may recall Kimmel’s recurring end-of-show apologies to Damon, who was – we were supposed to believe – forever scheduled to appear but always being bumped because they’d run out of time. In 2006, however, they finally managed to squeeze him in…almost.

8. The Late Show with David Letterman (2006): Not that it’s so hard to do a Matthew McConaughey impression – hell, even *I* do one – but Damon really nails it here, especially at the very end.

9. CBS News RAW (2008): In fairness, it’s possible that Democrats will find Damon’s comments about Sarah Palin funnier than Republicans will, but, c’mon, anyone can appreciate the humor in his description of her candidacy as being like a really bad Disney movie. “‘I’m just a hockey mom, I’m from Alaska,’ and she’s the President, and it’s, like, she’s facing down Vladimir Putin and using the folksy stuff she learned at the hockey rink!” I’d pay to see that film. Well, a matinee, anyway.

10. Jimmy Kimmel Live! (2008): You knew it was coming. In fact, you probably thought that’s what that last “Kimmel” clip was going to be. At last, here’s what you’ve all been waiting for…

11. Entourage (2009): See, this is what happens if you don’t stick around ’til after the closing credits: you miss awesome moments like this one.

12. The Late Show with David Letterman (2009): I question the veracity of this story, but I laughed at it, anyway.

13. Jimmy Kimmel Live! (2009): How about another round of applause for Jimmy Kimmel, ladies and gentlemen? The man never fails to bring out the funny in Damon, and this behind-the-scenes look at the making of “The Informant!” keeps their collaborative winning streak going.


14. National Lampoon’s The Zaz (2009): National Lampoon hasn’t automatically equaled “funny” in a very long time, with their straight-to-DVD “comedies” (I use the word very loosely) doing no end of damage to the reputation of the institution that gave us “Animal House” and “Vacation,” but I have to admit that the schtick of superfan Matt Zaller made me laugh, particularly the way he pays tribute to Damon in song.

15. Team America: World Police (2004): Although you probably noticed that the rest of our list is chronological, we saved this one for last because it’s the only one on our list that doesn’t actually involve Matt Damon personally, but it was too funny to leave off altogether. There seems to be some uncertainty about whether it was Trey Parker or Matt Stone who provided the voice of Damon’s marionette likeness in this cult classic, but given the limited dialogue, it hardly matters.


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