Roy Waller (NICOLAS CAGE) is a single, self-employed man who suffers from obsessive-compulsive disorder and agoraphobia. Nevertheless, and with the help of medication, he's been wildly successful at his job that just so happens to be conning people out of their money.
When a shortage of pills sends him off the deep end once again, his partner in crime, Frank (SAM ROCKWELL), suggest that he see a psychiatrist. Roy then reluctantly meets with Dr. Klein (BRUCE ALTMAN) who uncovers that Roy was once married and could very well be the father of a 14-year-old. Upon Roy's urging, Klein agrees to call the ex-wife and find out. He then gives Roy the news that schoolgirl Angela (ALISON LOHMAN) is indeed his daughter.
The two soon met, with Roy both scared and excited to meet her, while she seems to enjoy his various tics and neurotic behavior. It's not long before she convinces him to tell her what he does for a living and he's soon teaching her the tricks of his trade. That eventually involves them and Frank trying to dupe Chuck Frechette (BRUCE McGILL) in a currency exchange con.
Yet, with Roy's paternal instincts taking over, he soon begins to think about quitting, a thought that exposes him to far more trouble than he ever imagined.