There are Rolexes, and then there are Rolexes. The latter are rare and sometimes obscure examples of the Rolex Daytona that have sold for dizzying amounts: starting at six figures and going all the way up to $3.7 million. They might have a special inscription on the dial, they might be one-of-three, or they might be covered in diamonds. And sometimes, they might just belong to one of the most legendary actors on the planet.

There's no one more qualified to explain the ins and outs of rarefied Rolexes than Paul Boutros, Senior Vice President of Phillips Auction House, which on October 26th will be auctioning Paul Newman’s recently-rediscovered Daytona in New York City. It’s not the only Daytona that’s noteworthy, or even the most expensive, but it’s the Grail. Here are some other eye-poppers.

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The Original

“The original Daytona is nicknamed the “Double Swiss Underline.” And it is an icon: introduced in 1963, with a Rolex 72B movement, packed with all of the details that Rolex nerds love to compare and contrast. The word “Swiss” appears twice on the bottom of the dial, and there’s an underline underneath the words “Rolex Cosmograph,” hence the nickname. It wasn’t until 1964 that the Daytona took on its name (did you know Rolex ), which makes these early one-year examples true rarities.

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Newman’s Own

In June of 2017, a man named James Cox decided to sell a watch. It was a Rolex Daytona, already one of the most valuable and collectible timepieces in the world—but this was even more special. On the back the case was engraved, in three lines: “Drive Carefully Me.” When Cox was younger, and dating the daughter of Paul Newman, the actor personally took it off his wrist and gave it to him: “Here,” , “here’s a watch. If you wind it, it tells pretty good time.” The watch was lost for decades until it resurfaced earlier this year, and on October 26th, . The official catalog estimate is $1 million—a paltry sum, as you’ll find out, among other Daytonas. And certainly for the most famous Rolex Daytona on Earth.

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Eric Clapton’s “Albino”

The “Albino” is an all-white Daytona with a black bezel, a fairly straightforward design and nickname. Only this one belonged to one Eric Clapton. At a Christie’s auction in 2008, it sold for $505,000, then the most expensive price ever for a Daytona. Two years ago, it went up for auction again. : $1.4 million. “It was the Clapton Albino Daytona that, to many, really ushered in the modern era of mega vintage Rolex collecting,” . That record didn’t last long.

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Signed, Sealed, Delivered

Only a handful of retailers around the world were allowed to place their name alongside Rolex's on the dial, including Tiffany and Co., in Texas (shown here), Beyer in Zurich, Germany—a retailer linked to Rolex founder Hans Wilsdorf —and , in Venezuela. “To be able to do that,” says Boutros, “Rolex must’ve viewed these particular retailers in very high regard. Out of 100 retailers around the world, Rolex said yes to maybe 10 of them, ‘You can have similar provenance on the dial, next to our name.’”

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The Big Red

The fun thing about watch nerdism are all of the nicknames. In the world of Daytonas there’s Big Red, possibly the most handsome distillation of the Daytona design: contrasting dial, the bold red text that reads DAYTONA, all outlined by a black ceramic bezel. Fun fact: Ryan Seacrest has one, Boutros informed us, one celebrity capable of having good taste.

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An “Entry-Level” Daytona

“Wristwatch collecting is quite young,” says Boutros. “It only started to take off in the mid-1980s. One of the most important watches that fueled that growth is the Daytona.” What if you’re not yet ready to jump into a $3 million timepiece? Boutros kindly directs you to what’s known as the Reference 16520, a stainless-steel version of a revolution. In 1987, Rolex phased out its manual-wind Daytonas in favor of the Calibre 4030, a Zenith movement that Rolex modified heavily for accuracy. It set the template and movement for the modern Daytona, and you can find one for about the same price—minus the three-to-five-year waiting list.

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The Lemon Legend

You are looking at : $3,717,906, to be exact, as the hammer struck at Phillips Geneva Watch Auction in May of 2017. This yellow-gold Daytona Reference 6263 is also known as the “Lemon,” for good reason, and just one of three known to exist with this color scheme.

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The 24-Hour Winner

Tough it out to win your class at the Rolex 24 At Daytona and you receive a Rolex Oyster Perpetual Cosmograph Daytona, engraved on the back with the enviable words “24 Hours Winner.” It’s a hell of a conversation piece, and a rightful heirloom—something you’d want to hold on forever as a testament to your skill and accomplishment. But occasionally, one is up for grabs. “In November 2016,” said Boutros, “we had one of those award-winning watches in the sale. Usually, that's because the driver won the race a year or two prior. So they had multiples.” That makes more sense: if you’re good enough to win at Daytona a few times, , what’s one more watch?

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Paul Boutros/Phillips
Diamonds Are Forever

In the early 1990s, Rolex became one of the first watchmakers to set rare diamonds into its production line, giving these bejeweled beauties a spot in its catalogs. Hence, this example, known as ":" rendered in 18-karat gold, with a dial full of diamonds, and emerald markers to boot, Phillips sold this particular example for around $345,000 in a 2016 auction.

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