Roy: Con artist. Flim-flam man, grifter, loser, matchstick man... Whatever. Take your pick.
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...
This film provides examples of:
- Abandoned Hospital Awakening: What hospital?
- Awkward Father Daughter Bonding Activity: Averted. Roy and Angela have a great time together conning people.
- 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.
- Bittersweet Ending: It starts out looking like a textbook case of a Downer Ending, but twists 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 hold a grudge against her.
- Blowing Smoke Rings: Frank tries this at the airport with little success.
- 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.
- Invoked with the gift shop ashtray that Angela bought, which allegedly helped Chuck to track her down.
- The Con: Well yah.
- Con Man: Also yah.
- The Con Within a Con: The "big hit" on Chuck, Angela's arrival, and Roy's visits with Dr. Klein are all part of a big con by Frank against Roy.
- Corruption by a Minor: Played with; Angela coerces Roy into recruiting her into his con against Chuck, but she's not really a minor.
- Daddy's Little Villain: Angela, who proves to be just as cunning as Roy. Justified as she is playing a role as part of the con against him.
- The Ending Changes Everything: When Roy discovers his hospital room isn't a hospital and gets the letter from Frank, he (and the viewer) realizes that the events most of the movie has been one long con against him.
- Evil Parents Want Good Kids: Roy, despite his long and checkered past, is appalled when he learns Angela isn't a innocent little waif; he is repeatedly shocked at her poor study habits, juvenile delinquency, and eagerness for con jobs.Angela: "Teach me something! A con."
Roy: "I'm not teaching you anything."
Angela: "Why not?"
Roy: "Because you're far too bright and innocent and beautiful and I'm not going to screw that up like everything else."
- The Film of the Book: The movie is based on the book of the same name, by Eric Garcia.
- Flipping the Bird: Angela gives the double finger at the airport cafe as part of her scheme.
- Gambit Roulette: The last major con did use some Batman Gambit aspects to know the mark, but still required some things to go exactly right.
- That Roy would 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 try to talk to his ex-wife, and wouldn't find 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.
- Idiot Ball: Roy's phobic nature kept him from talking to his ex-wife, which would have blown the scam.
- 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: 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 is Angela conning people with her father and conning him because she's not really his daughter.
- Luke, You Are My Father: Exploited. It's a scam.
- Madness Mantra: "Pygmies! Pygmies!"
- Massive Multiplayer Scam: Roy thinks he is working with Frank to take Chuck Frechette for $80,000. In reality, Frank, Angela, Dr. Klein, and several other accomplices are all working together to take Roy for the million-plus in his safe deposit box.
- Neat Freak/Super OCD: Roy is obsessive with cleanliness — he can't stand to be outdoors, insists his visitors remove their shoes, opens and closes the front and back door three times, and spends an entire day cleaning the house out of fear it may be dirty.
- No Honor Among Thieves: Not only does Frank run a Massive Multiplayer Scam against Roy, but "Angela" later reveals that he cheated her out of her cut, as well.
- Older Than They Look: "Angela" is in her twenties, not a teen.
- Parental Hypocrisy: Roy the Con Man is strongly opposed to teaching Angela his tricks of the trade, and makes her return the takings of her first scam.Roy: "I told you I'd teach you a con. I didn't say I'd let you get away with it."
- Pet the Dog: Downplayed. Despite running a long con on Roy and cheating Angela out of her cut, Frank is honorable enough not to clean Roy out completely, leaving a stack of hundreds behind for him.
- 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.
- Rewatch Bonus: Especially after the twist, a lot of characters take on a new light.
- Dr. Klein's mannerisms around Roy. While he's putting on a good performance, there are times he looks uncertain or even guilty around Roy as the con escalates.
- Also, anyone scratching their head that the doctor would just hand off pills to a patient.
- Shout-Out: Roy's partner, "Frank Mercer", is named after Frank Sinatra and Johnny Mercer. Both artists are featured prominently in the soundtrack.
- The Shrink: Dr. Klein is aiding Roy with his OCD because it's part of a con.
- Suddenly SHOUTING: The aforementioned comment about pissing blood.
- Title Drop: You're a con man? - Con artist. A flimflam man, matchstick man, loser.
- Violin Scam: Roy uses two variations of this scam, one with a water filtration system (the mark buys it to avoid paying taxes for a nonexistent European vacation), and one with a "winning" lottery ticket.
- Voiceover Letter: Frank Mercer's farewell letter to Roy.
- What Happened to the Mouse?: Frechette's murder is never resolved. The audience doesn't find out if he actually died or was in some way part of the larger con.
- 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.