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).