When Cool Was a Crime: 1968’s Suave Middle-Finger to the System
Once upon a time—before billionaires wore hoodies and crime thrillers were CGI theme parks, there was The Thomas Crown Affair (1968). Directed by Norman Jewison and starring a Steve McQueen so slick he practically left oil stains, this was the movie that made robbing a bank look like an elite leisure activity for the absurdly well-dressed.
Imagine if Jeff Bezos took up heisting as a side hustle and seduced insurance investigators for fun. That’s Thomas Crown.
Released in an era teetering between sexual revolution and social collapse, this stylish crime caper is less about suspense and more about performance. It’s Ocean’s Eleven before Clooney, before Soderbergh, before anyone thought robbing a bank should involve actual tension. Because in The Thomas Crown Affair, everyone is just too cool to sweat.
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The Plot: Millionaire Gets Bored, Robs a Bank, Shrugs
Thomas Crown (McQueen), a self-made Boston businessman, spends his free time masterminding the perfect bank robbery, not out of need, but because being rich, bored, and male in the 1960s was basically a gateway drug to morally ambiguous hobbies.
He recruits a crew of disposable goons, all of whom don’t know each other (a surprisingly modern touch), and orchestrates a daylight heist using Rolls-Royces and walkie-talkies like it’s a particularly stressful episode of Mad Men.
Enter Vicki Anderson (Faye Dunaway), the insurance investigator who sniffs out Crown’s involvement like a bloodhound in Chanel No. 5. What follows is a seductive game of cat and mouse, but with chess metaphors, sexually charged glances, and one of the most notorious kiss scenes ever committed to film. The Thomas Crown Affair Is erotic tension dipped in 1960s ennui and lightly battered with tax evasion energy.
Style Over Substance – And That’s the Point
Is the plot airtight? Not really. Is the pacing swift? Eh. But you don’t watch The Thomas Crown Affair for narrative propulsion. You watch it for vibes.
This film oozes late-60s aesthetics: split screens, jazzy montages and so many turtlenecks you’ll think you’ve stumbled into a Wes Anderson fever dream. Steve McQueen doesn’t just wear suits, he inhabits them, like some kind of smug fashion golem. Faye Dunaway, meanwhile, treats the screen like her own personal runway slash psychological warfare arena.
The real heist here isn’t the money, it’s how they stole entire scenes with nothing more than a stare and a cigar.
Steve McQueen as Thomas Crown: The Original “Rich Men North of Boston”
Crown is the sort of man who thinks morality is a suggestion. He doesn’t steal because he needs to. He does it because why not? He’s rich, he’s bored and the world is a playground for people who can afford to bend it. Sound familiar?
In The Thomas Crown Affair He’s less of an antihero and more of a proto-tech bro who discovered existentialism, but instead of reading Camus, he robbed a bank and bought a glider.
McQueen plays him with a detached charm that suggests he’s simultaneously orchestrating a heist and wondering what’s for lunch. There’s something chillingly relevant about a man who breaks the law not out of desperation, but for amusement. It’s capitalism’s final form: crime as leisure activity.
Faye Dunaway as Vicki Anderson: Femme Fatale or IRS Auditor with Killer Cheekbones?
Faye Dunaway’s Vicki is the exact opposite of every simpering love interest in late-60s cinema. She’s sharp, elegant and clearly smarter than everyone else in the room, including the audience.
She doesn’t chase Thomas Crown. She hunts him, with the calculated coldness of someone who knows they could end this man’s life with a well-placed audit. Yet, she’s also seduced, not just by Crown, but by the game itself. It’s a rare film where the femme fatale is also the most emotionally honest person on screen.
And yes, the infamous chess scene. Two words: psychosexual warfare. If you ever wanted to watch two people mentally undress each other while moving bishops around, congratulations, your moment has come.
The Soundtrack: Michel Legrand’s Jazzy Despair
Ah yes, The Windmills of Your Mind. A song so existentially disorienting it feels like someone turned an anxiety spiral into a melody.
Michel Legrand’s Oscar-winning score doesn’t just accompany the film, it actively gaslights you into thinking time is a flat circle and morality is a mood. If you’ve never heard orchestral jazz make you question your life choices, you haven’t lived.
The Ending (No Spoilers, but Prepare for Smugness)
Let’s just say that the ending is as stylishly ambiguous as the rest of the film. It doesn’t wrap things up so much as tie them in an artful knot and toss them into a convertible.
The message is clear: in a world ruled by the wealthy, crime doesn’t pay… unless it’s wearing a silk cravat and drinking scotch at noon.
Legacy: Remade, Rehashed, but Never Replaced
Yes, there’s the 1999 remake with Pierce Brosnan and Rene Russo. It’s decent. It even had a sex scene that involved actual nudity rather than suggestive chess pieces. But it lacks the original’s weird alchemy of mid-century nihilism and couture. It’s glossy where the original is grimy, sexy where the original is unsettling.
There’s also a reboot in development, because of course there is. Presumably, Thomas Crown will now be an NFT millionaire who steals rare Pokémon cards for sport.
My Final Thoughts: A Classy Middle Finger to the System
The Thomas Crown Affair (1968) is a cinematic Rorschach test. Is it a romance? A satire? A warning about unchecked privilege? Yes. And also: who cares? It’s fun, it’s weirdly sexy and it makes existential malaise look like a Vogue photoshoot.
You don’t watch it to feel good. You watch it to feel expensively bad.
If You Like The Thomas Crown Affair, I Recommend These Movies:
Charade (1963) – Like Thomas Crown with Hepburn, Paris, and a higher body count in cashmere.
The Italian Job (1969) – Dapper heists, fast cars, and more swagger than a Savile Row catwalk.
Catch Me If You Can (2002) – Crown’s slickness meets con-man chaos with DiCaprio grinning through every felony.
The Thomas Crown Affair
Thomas Crown
Vicki Anderson
Eddy Malone
Erwin
Sandy
Abe
Gwen
Jamie
