Debonair leading men, iconic cinema heroes, and the luxury timepieces that wear them.
Sometimes, the wardrobe makes the character. But more often than not, it’s the timepiece that completes the look. Throughout film history, there have been standout moments when the watch doesn’t just complement the scene—it steals it. These menswear milestones echo through time, inspiring generations of men to emulate their favorite movie icons. Here are five moments where watches helped shape cinema and pop culture as we know it…
Dr. No (1962) and Goldfinger (1964)
James Bond has long been synonymous with outlandish gadgets—especially in the 1960s, when Sean Connery’s 007 ignited the playful spirit of the series’ early years. Some inventions worked better than others, but if there was one thing Bond could always count on, it was his timepiece.
The first watch worn by the legendary super spy was the Rolex Submariner Ref. 6538 (later nicknamed the “James Bond Submariner”) in his official cinematic debut, Dr. No (1962). Designed by Rolex in 1953 as a diving watch, the Submariner wasn’t a household name until Connery strapped it on for his Jamaican island adventure. Its global fame was sealed in Goldfinger (1964) two years later, when Bond, dressed in a white dinner jacket, casually checks the time. The close-up of the Submariner became an instantly iconic watch moment, cementing its place in pop culture and launching a Bond–Rolex partnership that would endure for over 25 years.
Casino Royale (2006)
The last time a Rolex appeared in a Bond film was in 1989’s License to Kill, worn by Timothy Dalton. When Pierce Brosnan stepped into the role, he brought with him a new era and a new watch: the OMEGA Seamaster. OMEGA, Rolex’s biggest competitor at the time, entered the picture in 1995’s GoldenEye when costume designer Lindy Hemming felt the watch was perfectly suited to Bond’s background as a naval officer. Brosnan loved the look and kept it on his wrist for three more films. But the Bond–OMEGA partnership truly found its stride with the arrival of the Blonde Bond: Daniel Craig.
Longtime producers Barbara Broccoli and Michael G. Wilson were ready for a hard reset for the franchise. They sought a tougher, more grounded Bond (less gadgets, more grit), who would resonate with younger audiences and align with the cinematic realism of the 2000s. Enter Daniel Craig: every millennial’s favorite Bond. Controversial for breaking tradition with his fair hair and rough personality, Craig quickly redefined the role. This younger, steelier, more military-edged superspy knew how to wear a suit and throw a punch.
Naturally, he brought the OMEGA with him, but with a new, rugged elegance. In Casino Royale, his first outing as 007, Craig wears not one but two Seamasters: the Diver 300M and the Planet Ocean 600M. Did it have a built-in laser, like Brosnan’s? Of course not. It didn’t need to. It was simply an OMEGA.
READ ALSO: LOOK: All The Times James Bond Wore OMEGA’s Timepieces
Wall Street (1987)
How do you portray the ultra-wealth of a greedy, corrupt Wall Street broker in the 1980s? Easy—put a solid gold timepiece on his wrist. For Gordon Gekko, the Oscar-winning anti-hero played by Michael Douglas in Oliver Stone’s iconic film Wall Street, that watch was no other than the Cartier Santos.
While no official sources confirm why the costume department specifically chose the Santos, it’s no surprise the corporate raider gravitated toward Cartier—a brand synonymous with power, precision, and top-tier luxury. Thanks to Gekko (and Douglas, who wore it with the swagger of a man who owns the New York City trading floor), the Cartier Santos—particularly the 18k yellow gold model—surged in popularity among real-life Wall Streeters. It became a symbol of financial dominance and was considered the ultimate insider’s timepiece.
The Thomas Crown Affair (1999)
You thought you’d seen the last of Brosnan on this list? Think again. And ironically, it’s for playing yet another iconic pop culture figure—this time, not Bond, but Thomas Crown, the infamous art thief originally portrayed by Steve McQueen (whom we’ll get to later). In the 1999 remake of The Thomas Crown Affair, Brosnan brings suave, tailored cool to the role—in a film so slick and stylish, my very own brother credits it with sparking his love for watches.
In it, Brosnan wears a stunning Jaeger-LeCoultre Reverso, widely regarded as one of the most elegant dress watches ever made. With its unique reversible case and Art Deco design, the Reverso has long been a favorite among the high-society set. But here’s the twist: the JLC that Brosnan wears in the film is missing its logo. Why? Because of his OMEGA contract from the Bond franchise. Ironic—and oddly fitting for Thomas Crown, a man who, beneath the debonair exterior, is still a thief in disguise.
READ ALSO: Time Travel, But Do It With Longines
Le Mans (1971)
Steve McQueen undoubtedly earned his title as “The King of Cool,” and he cemented it with roles that celebrated fast cars, tough men, and devil-may-care charisma. From Bullitt and the original Thomas Crown Affair (both released in 1968) to Le Mans in 1971, McQueen embodied The Man’s Man. In Le Mans, he famously wore a TAG Heuer Monaco—known as Heuer at the time—which became iconic largely because McQueen personally chose to wear it on screen. Playing a race car driver, he turned the Monaco into a symbol of speed, rebellion, and effortless style.
In 2009, TAG Heuer re-released the Monaco in tribute to its legendary wearer. But for collectors, it’s the original watches worn during the film that have become a kind of horological Holy Grail. The first of four Monacos used in Le Mans sold at auction in 2009 for $87,600. The second went for $799,500 in 2012. A third, which McQueen gifted to his mechanic Haig Altounian on the final day of shooting, fetched a record-breaking $2.2 million at Phillips Auction in New York in 2020, becoming the most expensive Heuer ever sold. Most recently, a fourth watch resurfaced and was sold at Sotheby’s this past December for $1.4 million.
