A group of buddies make a bet that could save Michael Delaney’s (Jerry O’Connell) life. He owes a Vegas casino from a gambling spree and he needs the cash.

There is only one person standing in his way… Kyle (Jake Busey), a notorious womanizer and Michael’s competition to win the bet, the money and his life back. It seems hopeless, but Michael has a secret weapon… Natalie (Shannon Elizabeth).

Meet the Tomcats, a group of freewheeling, sex-fueled single buddies as they go up against each other in a betting pool that will leave the “last man standing” unmarried with the jackpot. The first victim, Steve (Horatio Sanz), succumbs to holy matrimony with the luscious Tricia (Jaime Pressly) in Las Vegas. Fast-forward seven years to today, when all of the Tomcats are now married and starting families with the exception of two confirmed bachelors…