Rachel Sterling in Tomcats (2001)

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Jerry O'Connell is a struggling cartoonist who really needs some moolah, and he just might get it if he can get his pal hitched in Tomcats (2001). Years ago, Jerry and seven buddies made a pact that whoever was the last to marry would get a big honking cash reward they all set aside; now he and Jake Busey are the only bachelors left of the bunch. Because Jake is a total pig, the chances of him getting hitched are nil, but Jerry decides to give it the old college try, because when it comes to money he's high and dry. When he sets up jerky Jake with the stunning Shannon Elizabeth, things seem to be going according to plan . . . until Jerry himself starts falling for Shannon (and, of course, her mammary glands).