Taylor Peters (Matthew Broderick) is a television writer and producer working on a low-rated, little-respected half-hour sitcom. Once destined for bigger and better things, Taylor's compulsive gambling, recreational drug use and drinking all conspired to throw his career off the rails. After kicking the alcohol and drugs, he only has one more hurdle...the horses.

His beautiful twenty - year old niece Amanda (Brittany Snow) has her own habit to kick. Living in Las Vegas, working as a "dancer," her family has just discovered she is actually a prostitute, and they suspect hooking for drug money.

On their way home from an emergency family meeting, Taylor's wife Lorraine (Maura Tierney) finds recent racing stubs in Taylor's glove compartment. After years of standing by him, she leaves.

Taylor comes up with a plan: he'll win back his wife by doing the right thing. He'll go to Las Vegas, find Amanda, and deliver her to a rehabilitation center in Malibu. While he’s at it, he might even catch up with some old friends (like slimy casino host Steve Coogan). But besides that, it's strictly the business at hand—while he's there, he vows, he won't gamble a single cent, but things don't turn out quite as he'd planned.