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Cage plays Roy Waller, an obsessive-compulsive, agoraphobic, germaphobic con-artist residing in Los Angeles. His partner is Frank Mercer (Rockwell). The two operate a fake lottery, selling overpriced water filtration systems to unsuspecting customers; in the process, Roy has collected over one million dollars and has developed a crush on Kathy (Sheila Kelley), a cashier at a local supermarket. Roy was married long ago; his wife, Heather (Melora Walters), was pregnant at the time he divorced her. After Roy has a violent panic attack, Frank insists he see a psychiatrist. The psychiatrist, Harris Klein (Bruce Altman), contacts Heather, and reveals that Roy has a daughter, Angela (Lohman). Not long afterwards, Angela turns up on Roy's doorstep. It seems she wants to get to know the father she never had, and also, that she wants in on his and Frank's upcoming con...
- Babies Ever After: The last shot of the movie is of Roy standing with his new wife, Kathy, who is now pregnant with his child.
- Bavarian Fire Drill: The final part of the last major con. Frank's allies trick Roy into thinking that he's been arrested for Chuck Frechette's murder. Fearing for Angela (who he thinks is on the run from the police), he tells Dr. Klein the passcode to his bank account and has him pass it on to Angela so that she'll have enough money to escape. Armed with his passcode, Frank, Dr. Klein, and "Angela" (who isn't really Roy's daughter) steal all the money from Roy's account.
- Bikini Bar: Roy and Frank go to one for their first meeting with Chuck Frechette.
- Bittersweet Ending: It starts out looking like a textbook case of a Downer Ending, but manages to twist it into a Bittersweet Ending. Roy loses all of his money after being conned by the three people that he loves and trusts most, and he finds out that his daughter (who he owes his newfound happiness to) isn't really his daughter. Fast-forward one year: Despite all that's happened to him, Roy has successfully left his criminal past behind and conquered his neurosis, and he has a steady relationship with a woman he loves. When he encounters "Angela" again, he doesn't even hold a grudge against her.
- Chekhov's Gun: A literal example, with the gun that Roy keeps hidden in his garage. Angela uses it to kill Chuck Frechette after Chuck breaks into Roy's house and threatens him.
- The Con: Well yah.
- Con Man: Also yah.
- Corruption by a Minor
- Dawson Casting: Angela, although there is a reason.
- Directing Against Type: Ridley Scott, who is primarily known for big-budget thrillers and action epics, directs a quirky character-driven Black Comedy.
- The Ending Changes Everything
- Hey, It's That Guy!: Johnny Blaze teams up with Justin Hammer to swindle D-Day. Chaos ensues.
- Ho Yay: Frank often jokingly flirts with Roy, as if he enjoys how uncomfortable it makes him.
- Insistent Terminology:
Dr. Klein: What if you weren't a criminal?
Roy: I'm not a criminal, I'm a con artist. They give me their money.
- Ironic Echo: Several in the final scene between Roy and "Angela".
- First (Roy to Dr. Klein): "I'm not a criminal, I'm a con man. They give me their money." Later (Roy to "Angela"): "You didn't take it. I gave it to you."
- First (Angela to Roy): "If you're gonna get wet, might as well go swimming." Later (Roy to Angela): "If you're gonna go swimming, you're gonna get wet.
- Kinda Busy Here: Subverted. Frank calls Roy when he's having an OCD freak-out and obsessively cleaning his house, but Roy ignores him. Realizing what's going on, Frank keeps calling and being ignored for hours on end, trying to snap Roy out of it.
- Large Ham: "Hey, have you ever been dragged to the sidewalk and beaten till you...PISSED...BLOOD?!!!!"
- Little Miss Con Artist: The whole point of the film.
- Luke, You Are My Father: It's just a scam, though.
- Madness Mantra: "Pygmies! Pygmies!"
- Massive Multiplayer Scam: Although not as epic as in the book.
- Offstage Villainy: We eventually learn that Frank, "Angela", and Dr. Klein are all working together to con Roy. However, we almost never see any of them together, and we never see any of them planning, conspiring, or actively trying to take his money. In fact, by the time Roy figures out what's going on they've already cleaned out his account. Aside from a brief encounter with "Angela" one year later, he never sees any of them again.
- Placebo Effect: Roy finds out that Dr. Klein's pills are actually soy menopause supplements, which he gave to Roy to prove that he didn't need pills to conquer his OCD. Roy realizes that bonding with Angela has given his life meaning and helped him overcome his neurosis.
- Plot Sensitive Latch: To a suitcase.
- Shout-Out: Roy's partner, "Frank Mercer", is named after Frank Sinatra and Johnny Mercer. Both artists are featured prominently in the soundtrack.
- Super OCD: Roy.
- Voiceover Letter: Frank Mercer's farewell letter to Roy.
- Xanatos Roulette: The last major con relied on some pretty egregious coincidences. Namely:
- That Roy would actually put up with seeing a psychiatrist, and that he wouldn't just find some other way to get his pills.
- That he would still trust Dr. Klein after finding out that he lied about the pills.
- That he would never even try to talk to his ex-wife, and wouldn't end up finding out that she didn't have a daughter.
- That he would trust "Angela" enough to give her access to his account, even though he had only just met her.
- You See, I'm Dying: Parodied. In the scene where Roy refuses to answer his phone while he's cleaning, Frank keeps leaving him voicemail messages trying to snap him out of it. After he's been at it for a few hours, he half-heartedly tries to guilt-trip Roy into picking up the phone by claiming that he's dying.
Frank: Roy, normally I would never do this, but, well...I'm dying, Roy. It's my spleen. I, uh...can't feel my thumbs.
(cuts to a shot of Frank lying back on his couch, absent-mindedly eating a bowl of cereal and watching TV as he talks to Roy)