Tomcats (2001)

Name: Tomcats
Genre: Comedy, Romance
Released: 2001-03-30
Duration: 95 min
Cast: Jerry O'Connell, Shannon Elizabeth, Jake Busey, Horatio Sanz, Bernie Casey

The Last Man Standing Gets The Kitty.

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!