26. OId School (2003)
Director: Todd Phillips
Writer: Todd Phillips and Scot Armstrong
Stars: Vince Vaughn, Luke Wilson, Will Ferrell, Jeremy Piven, Ellen Pompeo, Craig Kilborn, Leah Remini
Quotable: [After funneling a beer] "Fill it up again! Fill it up again! Once it hits your lips, it's so good!"
Fun Fact: The guy who played the father of Ferrell's character's wife is actually the Ferrells' real-life accountant.
If not for the unfortunate casting of Luke Wilson as the film's lead protagonist, Old School would rank much higher on this list. This is a celebration of great comedy, though, so let's ignore Wilson's dull ass for the time being, which isn't tough to do at all. Old School, Todd Phillips' best film, lets Vince Vaughn and Will Ferrell run wild as Wilson's more dynamic counterparts.
Away from his partner-in-laughs Adam McKay for a change, Ferrell scores the deepest chuckles, whether he's streaking while inebriated or shooting a tranquilizer dart into his neck. Old School solidified both him and Vaughn as two of this generation's comedy giants. As for Luke Wilson, he's just blessed by association.