We’re diving into the archives to discover the most expensive Rolex watches ever sold at auction.

From the first ascent of Everest to the exploration of the Mariana Trench, and throughout many of humanity’s greatest adventures, Rolex was the brand keeping time. Eventually, it made its way to the silver screen—by the 1960s, Rolex watches started appearing on the wrists of Hollywood stars in films. From Pretty Woman to James Bond, Rolex timepieces became cinematic icons, but none more so than the one associated with American actor Paul Newman. So much so that one particular Daytona model came to be known simply as the “Paul Newman Daytona”.

Gifted to Paul Newman by his wife Joanne Woodward in 1968, the Paul Newman Daytona (Ref. 6239) went on to make history when it sold at auction in 2017 for $17.75 million, becoming the most expensive Rolex ever sold. Remarkably, the watch cost around $200 when it was first purchased.

Rolex watches, often with waiting lists just to buy them, have long attracted similar enthusiasm at auctions. Every year, they hit the block around the world, reaching multimillion-dollar prices. The “Paul Newman Daytona,” sold at Phillips in 2017, still holds the record as the most expensive Rolex to date.

In this article, we take a journey through the archives to round up the most valuable Rolex watches ever sold.

Paul Newman Daytona – 17.75 Million USD

The “Paul Newman” Daytona, gifted to one of the most iconic actors of all time by his actress wife Joanne Woodward, was sold at a Phillips auction in 2017 for $17.75 million. Collector Geoff Hess describes this legendary 1968 Rolex as follows: More than 400 people from around the world attended the auction where the most expensive Rolex in history was sold. The sale lasted approximately 12 minutes.