Tomcats

Tomcats is a 2001 film about a group of friends who make a bet that will award the man who remains a bachelor the longest a lot of money. The film stars Jerry O’Connell, Shannon Elizabeth, Jake Busey, Horatio Sanz and Jaime Pressly.

Jerry O’Connell plays Michael Delaney, a cartoonist who is deeply in debt because of gambling. Jake Busey and Horatio Sanz play Kyle Brenner and Steve. Steve is married to Tricia, who is played by Jaime Pressly, while Michael and Kyle are the only two friends who are still bachelors. Steve seems to have a happy marriage, while at the same time he wonders about his wife.

Michael and Kyle are womanizers. Michael’s plan to get out of debt involves trying to get Kyle married so that he can win the money from the bet. Michael finds a woman from Kyle’s past who he thinks Kyle may still have feelings for. Michael finds the woman, played by Shannon Elizabeth, and talks to her about his plan. They make a deal and she agrees to help him. Probably one of the biggest problems with his plan is that he falls in love with Natalie. Many comic situations occur after Michael realizes his feelings for Natalie.