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.

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.

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