This romantic comedy in the vein of
There's Something About Mary and
American Pie concerns the story of Michael Delaney (
Jerry O'Connell), a struggling cartoonist who makes a bet with seven buddies over who will be the last to marry. Several years later, the pot has boiled down to two: Michael, who is battling gambling debts in Las Vegas, and diehard bachelor Kyle Bremmer (
Jake Busey), who is a self-proclaimed ladies' man. Michael tries to get Kyle to wed within 30 days in order to rescue himself from financial turmoil. When Natalie (
Shannon Elizabeth) enters the picture as Kyle's new intended bride (as set up by Michael), she and Michael end up falling for one another, setting up a competition for her affections by the two men. Tomcats is the feature directorial debut for screenwriter Gregory Poirier. ~ Jason Clark, All Movie Guide