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It's too much to ask for a Freudian breakdown of the character's obvious neuroses - this is a National Lampoon film, after all - but I can't help thinking it would have been a comic goldmine.
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There's a briefly touched-upon subplot that makes a lame attempt to explain this clown's fear of the real world outside of school, but it's gone as soon as it crops up. Van Wilder's so enamored of his position as campus king of cool, however, that he's desperate to stay where he is. The meandering plot has Van Wilder cut off by dad Tim Matheson (Animal House's Otter) who feels that seven years of tuition payments is enough. It falls flat because it falls somewhere in the middle - unlike Van Wilder's beloved canine compadre, the film has no balls. It's not lewd enough to qualify as a gross-out comedy (although an endless shtick involving a bulldog with massive, pendulous testes is pretty godawful) and it's nowhere near as smart as Animal House - or even the underappreciated PCU. Reynolds is terrific, but he's trapped in a film that suffers from a massive identity crisis. Kilgore in Apocalypse Now, you just know this guy is going to walk away from life without a scratch on him. (Chase may still be alive, but the fluid comic timing that made his Gerald Ford pratfalls so memorable has been pushing up daisies for going on 20 years.) He's got that same goofball panache like Col. There are moments in Van Wilder - specifically the opening gag, in which Reynolds tries to comfort a depressed freshman about to end it all - in which Reynolds is clearly channeling the ghost of Seventies-era Chevy Chase. Reynolds is best known for his work on ABC's Two Guys and a Girl, and he uses the same easy smile and laconic grace here he's the anti-frat, a slick, know-it-all slacker with just enough good fortune to make the grade and keep out of the dean's way. As the titular college student drifting through his seventh collegiate year, he's the go-to party guy, the scammer, the BMOC with all the angles and the wherewithal to play them. It's a measure of Ryan Reynolds' not inconsiderable charm that this Animal House knockoff works as well as it does.