The Thomas Crown Affair

The Thomas Crown Affair (1968) is a heist movie by Normal Jewison, starring Steve McQueen and Faye Dunaway as, respectively, Thomas Crown, a millionaire businessman who has just pulled off the perfect crime, and Vicki Anderson, an independent insurance investigator contracted to investigate the heist who will get a portion of the stolen money if she manages to recover it. Crown obviously doesn't need the money, but he is constantly in search of diversions, welcoming Vicki's interest in him as a way to alleviate his boredom, even though she informs him from the start that she is investigating him. Their relationship evolves into a full-blown affair, complicated by Vicki's vow to recover the stolen money.

The Thomas Crown Affair was remade in 1999, starring Pierce Brosnan as Crown and Rene Russo as Catherine Banning, the insurance investigator looking into an art theft masterminded by Crown. Faye Dunaway plays a minor role as Crown's psychiatrist.

The Thomas Crown Affair contains examples of:

 * Anti Hero: both the leads.
 * Beleaguered Assistant: Thomas has one, who doesn't understand why the boss keeps complaining about boredom.
 * By the Book Cop: Eddie Malone, to a degree.
 * The Caper: Indeed, it was was almost called The Thomas Crown Caper.
 * Combat Pragmatist: Vicki is the detective's version, using every resource, and we do mean every, to win.
 * Clock King: Thomas' heist revolves around this.
 * Dating Catwoman / In Love With the Mark: Yes indeed.
 * Dirty Business: played with. Vicki makes no bones about being unscrupulous, and when Eddie calls her out on this, gives him a "Think Dirty" plaque.
 * The Faceless / The Voice: Thomas to his team.
 * Foreshadowing: After Vicki beats Thomas at a game of chess, he changes to a different game.
 * I Know You're Watching Me: Vicki isn't exactly subtle about keeping the heat on Thomas. He responds with various tricks on her agents.
 * Intimidating Revenue Service:
 * It Amused Me: Thomas' motivation.
 * Ivy League for Everyone
 * Karma Houdini: Thomas Crown.
 * Nice Hat: Eddie sports a fedora and Vicki has a variety of fancy hats, but Thomas' baseball cap counts purely on coolness points.
 * Operation Jealousy: a somewhat less complicated version than in the remake: he just starts going out with other women.
 * Orbital Kiss: One of if not the first example.
 * The Perfect Crime
 * Smart People Play Chess: The game loaded with more Visual Innuendo than you can shake a stick at.
 * Smoking Is Cool / Everybody Smokes: Vicki smokes cigarettes from a holder. Thomas smokes cigars.
 * Split Screen: Taken to an insane degree during the opening heist with multiple screens for the viewer to follow.
 * Swiss Bank Account
 * Sympathetic Inspector Antagonist: Eddie.
 * Take a Third Option
 * Tap On the Head: What Thomas does to one of the detectives watching him.
 * What the Hell Hero: Eddie calls Vicki out for extracting a confession from a man by kidnapping his son. She responds with an I Did What I Had to Do.

Tropes in the remake
"Thomas Crown: Do you want to dance, or do you want to dance."
 * Astronomic Zoom: The opening.
 * Gentleman Thief: Crown. This is more of a remake trait; in the original, he was merely bored.
 * Informed Attractiveness: Rene Russo, according to some.
 * Informed Ability: Catherine is presented as an intelligent, no-nonsense woman, but Crown plays her like a violin throughout the entire movie, and barring the final scene, she spends the last 15 minutes of the movie as a heartbroken emotional wreck.
 * Decoy Getaway / Lost in A Crowd / Needle in A Stack of Needles / Ringer Ploy: A sequence near the end where Crown enters the art museum and plainly shows himself to the security cameras, making sure everyone can see that he wears a trench coat and bowler hat and carries a valise. Then he walks off in a random direction -- and hundreds of confederates break out identical hats, coats and valises, and start walking all over the museum, switching valises several times while the guards scramble. Somewhere in the confusion Crown ditches his own hat and coat, and slips out a side entrance.
 * Distracted By the Sexy: Both Crown and Banning, to the point where it jeopardizes both of their plans.
 * Dress Hits Floor: Executed expertly.
 * Enforced Method Acting: The director told Pierce Brosnan to keep kissing Rene Russo even though she was pulling away, during a kissing scene near the end of the film. Russo was not told of this, so during the scene, she really was trying to stop the kiss.
 * Insecurity Camera: Subverted. There's a sequence near the beginning where a team of art thieves are performing an elaborate operation and one of them ends up dangling in full view of a security camera. This is seen in the main security room, but the camera operator is catatonic and doesn't actually do anything in response.
 * Trojan Horse: An upcoming exhibit being delivered to a museum. As a feint. Rene Russo even lampshades it.
 * Relative Error:
 * The Remake
 * Remake Cameo: Faye Dunaway as Crown's shrink.
 * Rich Boredom: Crown's motive.
 * Operation Jealousy: Crown likes Catherine, but he doesn't know if she likes him. He lets photos leak of him 'dating' a younger woman to see if he gets a rise out of Catherine. He does. They hook up.
 * Mating Dance: There is already subtext because of Banning's see-through dress, but Crown's quip sends it over the brink:


 * Nerds Are Sexy: Catherine Banning. The first part of her we meet is her legs.
 * Product Placement: Rene Russo practically chugs a Pepsi One with the label pointed directly at the camera.
 * Vapor Wear