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 … Jerry O'Connell, Shannon Elizabeth, Jake Busey, Horatio Sanz, Bernie Casey, Jaime Pressly, David Ogden Stiers Added on Netflix 2022-11-02. Youtube Trailer