Tomcats 2001
Directed by Gregory Poirier | Starring: Jaime Pressly, Bill Maher, Jerry O'Connell, Jake Busey
College buddies chip in and promise that the group's last unmarried man will collect a cash pot. Seven years later, the kitty is worth $500,000 -- money Michael needs to pay a gambling debt. Problem is, the only other single guy is a hopeless womanizer!.