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''The Thomas Crown Affair'' (1968) is a heist movie by Normal Jewison, starring SteveMcQueen 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 [[RichBoredom 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.
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!! ''The Thomas Crown Affair'' contains examples of:

* AntiHero: both the leads.
* BeleagueredAssistant: Thomas has one, who doesn't understand ''why'' the boss keeps complaining about boredom.
* ByTheBookCop: Eddie Malone, to a degree.
* TheCaper: Indeed, it was was almost called ''The Thomas Crown Caper''.
* CombatPragmatist: Vicki is the detective's version, using every resource, and we do mean ''every,'' to win.
* ClockKing: Thomas' heist revolves around this.
* DatingCatwoman / InLoveWithTheMark: Yes indeed.
* DirtyBusiness: played with. Vicki makes no bones about being unscrupulous, and when Eddie calls her out on this, she gives him a "Think Dirty" plaque.
* TheFaceless / TheVoice: Thomas to his team.
* {{Foreshadowing}}: After Vicki beats Thomas at a game of chess, he [[TakeAThirdOption changes to a different game]].
* IKnowYoureWatchingMe: Vicki isn't exactly subtle about keeping the heat on Thomas. He responds with various tricks on her agents.
* IntimidatingRevenueService: [[spoiler: Vicki wins by siccing the IRS on Thomas: they can nail him if he spends any of the money he stole.]]
* ItAmusedMe: Thomas' motivation.
* IvyLeagueForEveryone
* KarmaHoudini: Thomas Crown.
* NiceHat: Eddie sports a fedora and Vicki has a variety of fancy hats, but Thomas' baseball cap counts purely on coolness points.
* OperationJealousy: a somewhat less complicated version than in the remake: he just starts going out with other women.
* OrbitalKiss: One of if not the first example.
* ThePerfectCrime
* SmartPeoplePlayChess: The game loaded with more VisualInnuendo than you can shake a stick at.
* SmokingIsCool / EverybodySmokes: Vicki smokes cigarettes from a holder. Thomas smokes cigars.
* SplitScreen: Taken to an insane degree during the opening heist with multiple screens for the viewer to follow.
* SwissBankAccount
* SympatheticInspectorAntagonist: Eddie.
* TakeAThirdOption
* TapOnTheHead: What Thomas does to one of the detectives watching him.
* WhatTheHellHero: Eddie calls Vicki out for extracting a confession from a man by kidnapping his son. She responds with an IDidWhatIHadToDo.

!! Tropes in the remake
* AstronomicZoom: The opening.
* DecoyGetaway / LostInACrowd / NeedleInAStackOfNeedles / RingerPloy: 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.
** The scene also serves as a protracted reference to Crown's favorite possession being Creator/ReneMagritte's "The Son of Man", which depicts a man wearing a similar hat and coat. The decoys even have copies of the painting in their valises.
* DecemberDecemberRomance: After a recent slew of films with a downright ridiculous age disparity between the male and female leads, many critics praised the fact that ''both'' of this movie's leads were over 40.
* DistractedByTheSexy: Both Crown and Banning, to the point where it jeopardizes both of their plans.
* DressHitsFloor: Executed expertly.
* [[EccentricMillionaire Eccentric Billionaire]]: Crown.
* EnforcedMethodActing: 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.
* GentlemanThief: Crown. This is more of a remake trait; in the original, he was merely bored.
* InformedAttractiveness: Banning, according to several of the detectives. Not an obvious case of this trope, especially as she's played by ex-model Rene Russo, and her beauty isn't plot-relevant (her ''personality'', on the other hand...)
* InformedAbility: 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.
** She does home in on Crown in the first place, however, and for most of the film both she and Crown are way ahead of the cops.
* InsecurityCamera: 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 reading and doesn't actually do anything in response.
* MatingDance: There is already subtext because of Banning's see-through dress, but Crown's quip sends it over the brink:
-->'''Thomas Crown:''' Do you want to dance, or do you want to '''dance'''.
* NerdsAreSexy: Catherine Banning. The first part of her we meet is her legs.
* OperationJealousy: Crown likes Catherine, but he doesn't know if she likes him. [[spoiler:He lets photos leak of him 'dating' a [[RelativeError younger woman]]]] to see if he gets a rise out of Catherine. He does.
* {{Oxbridge}}: Crown is an alumnus of Oxford.
* [[PoliceAreUseless Security Guards Are Useless]]: Subverted during the first heist; Bobby the Museum Guard and his cohort easily hand the hired thieves their asses.
* ProductPlacement: Rene Russo practically chugs a Pepsi One with the label pointed directly at the camera.
** Interestingly enough, this particular instance is commonly CGI'd out in many versions, and/or replaced with another Pepsi product. There are several other minor product placements that change labels in various versions (i.e. broadcast, airline, theatrical, dvd, etc.)
* RagsToRiches: Crown is a billionaire now, but he attended university on a boxing scholarship.
* RelativeError: [[spoiler: The young hot girl seen dancing with Crown and in his bedroom is actually his ward.]] He could've easily told Catherine this, but he [[InvokedTrope invoked this trope]] because he wanted to test her.
* TheRemake
* RemakeCameo: Faye Dunaway as Crown's shrink.
* RichBoredom: Crown's motive.
* TheShrink: Crown attends sessions with perhaps the worst shrink ever, a woman who holds him in open scorn and repeatedly laughs in his face while he's trying to tell her how he feels. No wonder the guy has trust issues.
* TrojanHorse: An upcoming exhibit being delivered to a museum. As a feint. Denis Leary even lampshades it.
* TheUnreveal: How Crown [[spoiler:stole the second painting at the end]] is never explained.
* VaporWear: Possibly one of the greatest ever filmed. The shear dress that Banning wears to the dance was literally the only thing actress Rene Russo was wearing, and was so gossamer thin that extra care had to be taken to (not) light the scene so as to keep her from appearing naked on film. Russo has stated that the whole scene was incredibly uncomfortable to film, as she was (for all purposes) completely naked for everyone on set to see. The final film managed to hide this fact in its entirety, giving only the impression of an '''insanely''' sexy dress. [[spoiler: Reinforced immediately thereafter by DressHitsFloor in the next scene]]

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