Movie remakes usually suck. Honestly, that’s just the rule. But when you look at the cast of the Thomas Crown Affair, you’re actually looking at a rare case where lightning managed to strike the same spot twice, just in totally different ways.
In 1968, Norman Jewison gave us Steve McQueen and Faye Dunaway. They were cool. They were icy. They played a chess game that somehow felt more scandalous than most modern R-rated movies. Then 1999 rolls around, and John McTiernan taps Pierce Brosnan and Rene Russo to do it all over again in New York.
People still argue about which pair did it better. It’s not just about who’s a better actor; it’s about the vibe. The 60s version was all about that gritty, split-screen, New Hollywood energy. The 90s version? That was pure, high-gloss billionaire escapism.
The 1968 Originals: McQueen and Dunaway
Steve McQueen wasn’t actually the first choice for Thomas Crown. Hard to believe now, right? Directors originally wanted Sean Connery or Richard Burton. McQueen was known for playing "down and dirty" blue-collar rebels—think The Great Escape or The Magnificent Seven. He had to fight for the role of a millionaire mastermind. He even had to prove he could wear a three-piece suit without looking like he was playing dress-up.
Faye Dunaway was fresh off the success of Bonnie and Clyde. She didn't just play Vicki Anderson; she embodied this hyper-stylized, fiercely independent investigator who was way ahead of her time.
The supporting players in '68 added a lot of texture too:
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- Paul Burke played Detective Eddy Malone, the straight-laced foil to Crown’s elegance.
- Jack Weston was Erwin Weaver, the getaway driver who was basically a "sap" caught in a high-stakes game.
- Yaphet Kotto made a brief but memorable appearance as Carl, one of the heist men.
The 1968 film relied heavily on silence. McQueen was famously laconic. He didn't need to explain his motives. He was just bored and rich. That's a scary combination.
The 1999 Power Couple: Brosnan and Russo
Fast forward thirty years. Pierce Brosnan is the biggest star on the planet thanks to Bond. He produced the remake himself because he wanted to play a different kind of "gentleman thief." Unlike McQueen’s Crown, who robbed banks for the thrill of the chaos, Brosnan’s Crown stole for the art. Specifically, a Monet.
But the real secret weapon of the cast of the Thomas Crown Affair remake was Rene Russo.
Casting an "age-appropriate" woman opposite Brosnan was a huge deal at the time. She wasn't some 22-year-old starlet. She was Catherine Banning, a world-weary, sharp-as-a-tack insurance bounty hunter. She was his equal. While Dunaway’s Vicki felt a bit "model-like" at times, Russo’s Catherine felt like she’d actually lived a life.
The Brilliant "Full Circle" Cameo
One of the coolest things about the 1999 version is the inclusion of Faye Dunaway. She doesn't play Vicki, obviously. Instead, she shows up as Thomas Crown’s psychiatrist.
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It’s a meta-commentary on the whole franchise. She sits there, listening to this new version of the man she once chased on screen, telling him he’s a "prowler" who’s afraid to get close to anyone. It’s a passing of the torch that actually works.
Supporting Cast: New York vs. Boston
The 1999 remake moved the action from Boston to Manhattan, and the supporting cast reflected that bigger, noisier energy.
- Denis Leary as Michael McCann. He’s the grumpy, blue-collar NYPD detective who hates everything about Crown’s lifestyle. He provides the humor that the 1968 version lacked.
- Frankie Faison as Paretti. A solid, grounded presence that balanced out Leary’s frantic energy.
- Ben Gazzara as Andrew Wallace. He plays Crown's lawyer/friend with that classic, old-school Hollywood gravitas.
The 1999 film also featured Fritz Weaver and Mark Margolis (long before he was Hector Salamanca in Breaking Bad). It’s a stacked deck.
The Heist Styles
In the original, the heist is violent. It’s a bank robbery. Smoke bombs, guns, and a lot of tension. The cast of the Thomas Crown Affair in '68 had to play it straight and dangerous.
The 1999 version is bloodless. It’s a puzzle. Crown uses "the Trojan Horse" trick with thermal heaters and bowlers hats (a nod to Magritte’s The Son of Man). This change shifted the tone of the performances. Brosnan’s Crown is smug. He’s having a blast. McQueen’s Crown felt like he was exorcising some deep, dark demon.
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Why the Casting Still Works
People still watch these movies because the chemistry is undeniable.
In the '68 chess scene, you can practically see the sparks flying between McQueen and Dunaway. It took days to film and featured some of the most famous "close-up" work in cinema history.
The '99 version swapped chess for a ballroom dance. It was sweatier, louder, and more overt. Russo’s dress in that scene—a sheer, beaded number—is basically a character in its own right.
What’s Next for Thomas Crown?
The story isn't over. A new version is currently in the works starring Michael B. Jordan. He’s also set to direct.
Following in the footsteps of McQueen and Brosnan is a tall order. Rumors suggest Taylor Russell might step into the investigator role. If they can capture half the charisma of the previous casts, they might actually pull it off.
Actionable Insights for Fans
- Watch the 1968 version if you want a masterclass in "cool" and 60s cinematography. It’s a slower burn, but the payoff is legendary.
- Watch the 1999 version if you want a fast-paced, sexy thriller with a killer soundtrack (that Nina Simone cover of "Sinnerman" is unbeatable).
- Compare the endings. The two movies handle the "will he or won't he" escape very differently. One is a cynical nod to the 60s, and the other is a romantic 90s grand gesture.
If you're looking to dive deeper into the filmography of the cast of the Thomas Crown Affair, start with Steve McQueen’s Bullitt for more 60s grit or Rene Russo in Nightcrawler to see her incredible range years later.
Explore the filming locations in Boston for the original, specifically the Beacon Hill area, which still looks much like it did when McQueen walked those cobblestones. For the remake, the Metropolitan Museum of Art was the inspiration, though most of the museum interior was actually a massive set built in New York.