Bob's Watches Bob's Watches Jared Paul Stern
The job of being a Rolex brand ambassador, officially known as “testimonee,” is one of the sweetest rewards of success any master of their field can achieve. The iconic Swiss watch brand has dozens of such carefully-selected personages on their payroll, though the relationship is usually presented as more of honorific than remunerative. However, longtime testimonee Roger Federer, for example, was reported to have signed a deal with Rolex in 2006 worth $15 million, in addition to being gifted lots of beautiful Rolex watches.
Rolex testimonees are mainly concentrated in the world of sports – in 1967 Arnold Palmer became the first golfer to join their ranks, which now includes Tiger Woods, Scottie Scheffler, Jannik Sinner, Coco Gauff, Carlos Alcaraz, Sir Jackie Stewart and equestrienne Zara Tindall to name a few; but also include a number of explorers, environmentalists, musicians and high profile figures from the world of cinema, including James Cameron, Martin Scorsese, and now, DiCaprio. These iconic figures have all been spotted wearing Rolex sports watches. The brand often refers to them collectively as the “Rolex Family.”
Whether it is part of the contractual obligation or not – and we have to think that there is some kind of clause to that effect – Rolex Testimonees tend to not engage in controversial behavior. To their credit however, Rolex isn’t afraid to consider the bigger picture and not be swayed by sensationalism; most notably signing Tiger Woods in 2011 after scandalous media reports had cost him other endorsements, keeping him on during a long period of injury and recovery leading up to his return to the field at the 2022 Masters.
DiCaprio is of course often in the news, and not always for his cinematic endeavors. His love life for example is colorful at best. However the Oscar winner is widely considered one of the finest actors of his generation, and it seems certain that he has many more honors to come. He has also been an outspoken advocate and financial supporter of environmental causes, the latter prominently cited by Rolex on its new page dedicated to the entertainment star. Like Tiger Woods, DiCaprio was once a TAG Heuer brand ambassador, so this is a major step up, horologically speaking.
In his younger years, while being sponsored by TAG, DiCaprio of course wore many of their nicer watches and seemed fairly content with that level of low-range luxury. In 2022 however, he was spotted wearing the highly coveted Tiffany dial Patek Philippe Nautilus 5711/1A, perhaps indicating a newfound interest in ultra-high-end timepieces. But in between he has at various times been seen wearing a variety of Rolex Daytona models, which in retrospect makes his new partnership with Rolex seem somewhat inevitable.
With any and every Rolex Daytona now available to him, we can make a safe bet that we’ll see more and more of them on Leo’s wrist. Here’s a rundown of every Daytona he has worn so far:
Rolex Daytona 16520 “Zenith”
The earliest documented Rolex seen on Leo’s wrist, from the 1990s, is a true icon, predating the ceramic-bezel era and therefore holding more appeal for connoisseurs than trendsetters. This black-dial Rolex 16520 watch may well have been gifted to the young actor following a photo or movie shoot, and one hopes that it remains in his collection to this day. In any case it seems to have definitely established his affinity for Daytonas.
Rolex Daytona 116503
Several years ago Leo showed up to the Academy Awards with this two-tone, black dial Daytona strapped to his wrist. Two-tone Daytonas have never been as highly prized as the stainless steel or white-gold models, which is why this is considered a starter Daytona by some. The black dial version Rolex 116503 that Leo chose is less common and a little cooler than the white dial iteration in our opinion.
Rolex Daytona 166509 “Black Diamond”
This slightly stranger white-gold Rolex Daytona showed up on Leo’s wrist in 2016 at a gala auction benefiting his LDFoundation environmental charity. He consigned the watch, which most notably has diamond-set indexes and a black crocodile deployment strap, at the event, where it quickly sold thanks to its provenance and the “Best, Leo” engraving on the caseback.
Rolex Daytona 116509 “Racing”
As far as Daytonas go, this white gold Rolex 116509 model is somewhat polarizing. Some collectors award it icon status, while others say it is more “fail” than grail. Any precious metal Daytona is always going to retain significant value however, and this discontinued piece is relatively rare. The Arabic hour markers are a departure from the traditional Daytona dial, and this quirk turns some purist enthusiasts off.
Rolex Daytona 126529LN “Le Mans”
Leo’s latest and greatest Daytona is the unique and extremely coveted “Rolex Daytona Le Mans” version in white gold released in 2023 to commemorate the 100th anniversary of the 24 Hours of Le Mans race, of which Rolex has been a longtime sponsor. If this is the first new Rolex Leo has gotten under his partnership with the brand then we’d say he’s off to a flying start. Will we see him in a “Rolex Daytona Rainbow” watch next? Only time will tell….
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