Spoilers follow.
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Nicholas Van Orton
Portrayed By: Michael Douglas, Scott Hunter McGuire (as a child)
I don't care about the money, I'm pulling back the curtain — I want to meet the wizard.
- And Your Reward Is Clothes: At the denouement, he gets a t-shirt which reads: "I was drugged and left for dead in Mexico, and all I got was this stupid t-shirt.
- Book Safe: He keeps a revolver stashed away in a copy on To Kill a Mockingbird, which CRS knew about and loaded with blanks.
- Dark and Troubled Past: Witnessed — although from afar — his father's suicide.
- Driven to Suicide: Subverted. Believing he killed Conrad, he jumps into a glass-paned roof, only to be caught in a blanket.
- Jerkass: He's snarky and aloof towards everyone around him, and often ignores the well-being of others less fortunate than him. After losing all his money and being left for dead in Mexico, he starts to grow out of it and becomes a halfway decent — if unhinged — person.
- No Social Skills: He admits to being detached from society, and it shows. He can't even spit out an apology to Anson when he finds out he's innocent of any wrongdoing.
- Not My Driver
- Pet the Dog: Nicholas feels bad about getting Christine fired, so he offers to help find her a new job. She declines, but it's definitely a step up from his behavior earlier on in the movie.
- Properly Paranoid: What Nicholas thinks he is by the end of the film, but he's still not paranoid enough to see through the last layers of deception.
- Scary Surprise Party: Right after attempting suicide, then dropping into the dining hall where his surprise party takes place - not to mention the fact that his brother that he just shot (albeit with blanks) is presenting him with his birthday present.
- Took a Level in Badass: Putting it mildly.
- Took a Level in Kindness: Over the course of the movie, he learns a thing or two about being a nicer person and appears to have hung onto these lessons by the end.
- White Anglo-Saxon Protestant: He's a very affluent corporate executive. His mansion is lavish, his office has a shower, and he even has his initials on some of his shirts.
Conrad Van Orton
Portrayed By: Sean Penn
Call that number. They make your life fun.
- Cluster F-Bomb: "They just fuck you and they fuck you and they fuck you, and then just when you think it's all over, that's when the real fucking starts!"
- Troll: Even before the Game begins in earnest, Connie is quite the troublemaker. When meeting his brother for lunch, he pranks Nicholas with a fake sneeze, wears a shabby t-shirt, and lights up a cigarette.
Christine
Portrayed By: Deborah Kara Unger
Where'd you all go, you motherfucking fratboys?
- Double Reverse Quadruple Agent: She certainly keeps Nicholas guessing as to which side she's on... all the way to the end of the Game.
- Femme Fatale: Played with, deconstructed, and arguably double subverted by the end of the film.
- Going Commando / Skirts and Ladders: When Nicholas offers to lift her up through an elevator roof hatch after they get stuck, an embarrassed Christine reveals that she's not wearing anything under her short skirt. Given what happens later, this is likely deliberate to mess with the protagonist's head.
- Ms. Fanservice: She has no trouble stripping down to her red bra in Nicholas's office to take a shower, and he shows a human side by briefly ogling her body. It becomes a plot point when he recognizes her bra in one of the Polaroids at the faked Hookers and Blow party, and realizes she's part of the game.
Jim Feingold
Portrayed By: James Rebhorn
The game is tailored specifically to each participant. Think of it as a great vacation, except you don't go to it, it comes to you.
- I'm Not a Doctor, but I Play One on TV: Nicholas discovers the CRS representative is an actor when he sees him doing a drug commercial on TV. Which is Hilarious in Hindsight, since the actor who plays the actor playing the rep (James Rebhorn) is frequently a source of Hey, It's That Guy! in real life, most recently on White Collar.
Anson Baer
Portrayed By: Armin Mueller Stahl
There is no Baer/Grant Publishing without Anson Baer.
- The Man Behind the Man: What Nicholas thinks Anson is after the incident with the briefcase and the Polaroids at the hotel.
- Red Herring: Nicholas suspects Anson organized the game as revenge for Nicholas attempting to force him out of his publishing company; it doesn't help that Anson has a fondness for games and toys, according to his office decor. When confronted, Anson calmly tells him that he agrees it's time to retire and shows zero knowledge of the game, leaving Nicholas humiliated.
Samuel Sutherland
Portrayed By: Peter Donat
When Mr. Van Orton boards his plane on the morrow, he will have every contract, side agreement and addendum, the complete closing package, flawlessly revised.
- The Mole: Subverted brilliantly when Christine plays on the paranoia the Game has engendered in Nicholas.
