Roy Waller, portrayed by Nicolas Cage, is a seasoned con artist living in Los Angeles, California, who grapples with debilitating Tourette syndrome and obsessive-compulsive disorder. His compulsive need to manipulate every locking mechanism three times before opening it is just one facet of his life. Together with his partner Frank Mercer, played by Sam Rockwell, Roy runs a phony lottery scheme, selling overpriced water filtration systems—a strategy that sees them persuading customers to treat these costs as tax write-offs linked to extravagant prizes like a Chevy Blazer, a diamond necklace, or even a trip to Paris.
In their elaborate ruse, Roy and Frank masquerade as Federal agents, meeting their victims under the guise of investigating fraud. They obtain written consent to access the victims' bank accounts, ultimately siphoning the funds they discover. This fraudulent enterprise has netted Roy over one million dollars. Burdened by mental health issues including agoraphobia, mysophobia, and a relentless tic disorder that causes him to shout "Pygmies!" whenever startled, it's clear that Roy is a man at war with himself. He is particularly averse to what he calls Long Cons, which require extensive planning and intrigue.
The story takes a turn when Roy accidentally discards his medication down the sink. In a frantic search for stability, he learns his doctor, Mancuso, has fled town, prompting a chaotic cleaning spree that lasts until dawn. Following a crushing panic attack, Frank recommends Roy see psychiatrist Dr. Harris Klein (Bruce Altman). Seeking medication, Roy isn’t eager for therapy but is compelled to delve into his past relationships, primarily reflecting on his ex-wife, Heather (Melora Walters), who was pregnant during their divorce—a personal connection he hasn’t revisited in more than a decade.
After a therapy session, Klein reaches out to Heather, revealing that Roy has a 14-year-old daughter named Angela, brought to life by Alison Lohman. However, Heather is unwilling to communicate with Roy. When he and Angela finally meet, she questions him about his life, harboring suspicions about his criminal background. Their interaction introduces a youthful vigor into Roy’s life, prompting him to join Frank in planning a new long-term con targeting an arrogant businessman named Chuck Frechette (Bruce McGill).
As their con unfolds, Angela unexpectedly arrives at Roy's home seeking refuge after a dispute with her mother. This visit compels Roy to confront his life choices during therapy. He develops a platonic bond with Kathy, a grocery checkout clerk, which Angela notices. Meanwhile, Roy and Frank’s gamble on Chuck intensifies, as they pitch a dubious currency exchange scheme that ensnares Chuck’s interest and promise of profit.
However, as their con progresses, Angela's actions lead to explosive revelations, just as Roy reluctantly teaches her the art of deception. Tensions mount when Frank alerts them that Chuck is changing flight plans, prompting an improvised alliance with Angela’s role in the con. Yet, things spiral out of control when Angela's late return home ignites a conflict. After confessing his con artist identity, Roy finds himself engulfed in a series of events that culminate in a showdown where Angela takes drastic action to protect them.
Faced with the repercussions of their actions, Roy wakes up in a hospital, discovering that both Frank and Angela have vanished, leaving him disoriented and betrayed. Realizing he has been played, Roy unravels a shocking truth—the girl he thought was his daughter was nothing but a pawn in Frank's elaborate scheme. As he confronts Heather, he learns the tragic reality of their child—she had suffered a miscarriage years prior.
A year later, Roy has seemingly turned over a new leaf as a humble salesman. Fate intervenes when Angela and her boyfriend walk into his workplace, bringing a mix of emotions. While he confronts her about her connections with Frank, he ultimately chooses to forgive, acknowledging that embracing honesty has brought him more happiness. In an unexpected twist, Angela reveals she was never in on the con but promises she doesn't seek further entanglements, parting ways just as Roy heads home to his pregnant wife, Kathy, symbolizing the cyclical nature of life and redemption.
