Taylor Peters (Matthew Broderick) is a television writer and producer working on a low-rated, little-respected half-hour sitcom. Taylor was probably destined for better things, but his compulsive gambling, recreational drug use and drinking problem (now under control) all conspired to throw his career off the rails several years back. Now all he does is play the horses, but does his best to keep his wife Lorraine (Maura Tierney) in the dark about it.

Unexpectedly, Taylor and Lorraine are called to Lorraine's sister's house to deal with a family emergency: Taylor's twenty-year-old niece AmandaA (Brittany Snow) is living in Las Vegas where, it's been recently discovered, she's working as a prostitute. On their way home, Lorraine finds racing stubs in the glove compartment, and decides to leave Taylor. Lorraine decides not to come home.

Taylor comes up with a plan: he'll win back his wife's affections and trust by going to Las Vegas, finding Amanda and delivering her to rehab in Malibu. And while he's there, he vows, he won't gamble a cent. Alas, the best laid plans...