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Dating back to 1905, Rolex has long been amongst the most prestigious watchmakers in the world. However, while the watchmaker is reported to sell over 800,000 timepieces a year, there are some in the archives that are simply a cut above the rest – and it is these that earn a spot on the list of the most expensive Rolex watches ever sold.

Interestingly, while Rolex is known for its flashy diamond-encrusted watches (for example, the Rolex GMT Master II Ice which is covered entirely with stones), for the most part, it is often the more understated pieces with a storied history that have fetched the highest prices, rather than the showiest.

For example, the Daytona models were widely unpopular when they were first released but add sitting on the wrist of someone with a following like Paul Newman for a few years, and they were elevated to legendary status, with prospective owners jumping at the opportunity to buy a piece of Hollywood legacy.

So, without further ado, here are the most expensive Rolex watches to have ever been sold.

[See also: The Most Expensive Watches Ever Sold at Auction]

Cosmograph Platinum Zenith Daytona ref. 16516 – $3.2m, 2020

The first on our list of the most expensive Rolex watches is also easily one of the most identifiable. This particular Platinum Zenith Daytona features a striking dark blue lapis lazuli hardstone dial and is known to be incredibly rare, if not completely one of a kind.

The coveted platinum casing only added to this watch’s allure when it was brought to market for the first time in Hong Kong in 2020 with Sotheby’s. Here, it fetched an impressive $3.2m, instantly catapulting it to the Rolex hall of fame.

Cosmograph Daytona ref. 6263 ‘The Legend’ – $4.1million, 2017

rolex daytona legend watch

As one of just three Paul Newman Daytonas in a yellow gold oyster case, The Legend is considered one of the rarest Rolexes on the market / ©Phillips

When it went to auction in 2017, the Cosmograph Daytona ref. 6263 ‘The Legend’ fetched $4.1m, which at the time was the second-highest ever paid for a Rolex – seconded only by the Bao Dai. Though both watches have now been surpassed several times over, this unique Daytona has still retained its legendary status.

As one of just three Paul Newman Daytonas in a yellow gold oyster case, the eye-catching wristwatch is considered one of the rarest Rolexes on the market and is thought to be one of the earliest examples of iconic 6263 references.

The Bao Dai Rolex – $5.1 million, 2017

rolex bao dai watch

The Bao Dai Rolex is named after its previous owner, the last emperor of Vietnam / ©Phillips

The story of the Bao Dai Rolex is a well-known one amongst watch aficionados: while attending a convention in Geneva in 1954, the final emperor of Vietnam headed into a local Rolex boutique and requested that to be shown the rarest Rolex ever made.

The watch presented to him was a reference 6062 in yellow gold, with a black dial and diamond indices. Although there are known to be two other 6062s with diamond dials in circulation, the unique five-diamond layout of the Bao Dai makes it completely one of a kind.

The family first sold the watch in 2002 when it fetched $235,000, which was then the most ever paid for a Rolex. However, when it went to auction again in Geneva in 2017, it sold for $5.1m.

[See also: The Best Timepieces at the Only Watch 2021 Auction]

Paul Newman’s Rolex Daytona, ‘Big Red’ – $5.5 million, 2020

While Newman’s second Rolex Daytona didn’t quite live up to standards set by his ‘Exotic’ Daytona (more on that timepiece later), it slid into the spot of third most expensive Rolex ever when it went to auction in 2020, selling for an impressive $5.5m. As with the ‘Exotic’, ‘Big Red’ also features an engraving from Newman’s wife, albeit less clearly, which reads “Drive slowly, Joanne”.

With Newman supposedly having worn his ‘Big Red’ for 25 years (ten years more than the record-breaking ‘Exotic’, which he gifted to his daughter’s boyfriend), there’s no doubt that this watch has been present to some of the most iconic moments in Hollywood history. Newman gave the ‘Big Red’ to his daughter Clea just months before he passed, and it remained in the family until Clea allowed it to be sold in name of some of her father’s charitable causes.

Cosmograph Daytona ref. 6265 ‘Unicorn’ – $5.9 million, 2018

rolex daytona unicorn watch

The Daytona ref. 6265 ‘Unicorn is the only Rolex Daytona crafted out of 18-karat white gold / ©Phillips

The aptly named Daytona ref. 6265 ‘Unicorn’ was the only Rolex Daytona crafted out of 18-karat white gold, making it as rare as, you guessed it, a unicorn. So elusive is this watch that when it was first revealed to the public in 2013, many in the watch industry were baffled by its existence, despite the fact that it dates back to 1970.

Sold by prolific Rolex collector John Goldberger, the Rolex Daytona ref. 6265 fetched $5.9m when it went to auction in 2018 making it the second most expensive Rolex ever. Despite previously stating the Unicorn would never be for sale, Goldberger reconsidered when he realized the impact such a sale could have and donated the proceeds to the charitable foundation Children Action.

Paul Newman’s ‘Exotic’ Rolex Daytona 6329 – $17.8m, 2017

engraving on back of paul newmans rolex daytona exotic

Newman was pictured wearing his beloved Daytona at many a race, cementing its status as one of the most legendary watches to ever exist / ©Phillips

And finally, the most expensive Rolex to ever sell at auction: Paul Newman’s ‘Exotic’ Rolex Daytona 6329, which hammered for an unbelievable $17.8m (including fees) at Phillips Auction gallery in New York, 2017.

However, it is generally agreed that it isn’t the prowess of the watch itself that fetched the record-breaking price (in fact, this model was notoriously unpopular when it was first released in the 1960s), but rather the connection with Newman himself.

While this list isn’t short of Rolexes bearing the Newman seal of approval, this watch is particularly special given the personalized inscription from his wife, that reads ‘Drive Carefully Me’, following his notorious car crash. Newman was pictured wearing his beloved watch at many a race, cementing its status as one of the most legendary, and of course most expensive, watches to ever exist.

[See also: Watches and Wonders 2021: The Best New Timepieces]