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Tomcats (2001)
From Amazon:
One might reasonably expect Tomcats to be the Porky's of 2001: after all, it concerns a group of young, sexist morons and their fears and fantasies about young women. But Tomcats isn't quite as brain-dead as that, though it is phenomenally more neurotic. Jerry O'Connell plays one of two remaining bachelors within a group of wealthy pals who set aside a cash reward, years before, earmarked for the last among them to get married. O'Connell needs the money to pay off a gambling debt, but his problem is that the other bachelor is a horrendous pig (Jake Busey) unlikely ever to land a gal. A general mean-spiritedness flows...
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