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Feature: The best 25 Rolex watches

How on earth do you whittle down the very best 25 Rolex watches? By dispensing with any strict criteria and going with your gut instinct. Some make the grade for their association with a famous wearer, some for their technical accomplishments, and a few for their devastating good looks alone. Here, then, are 25 Rolexes that stand that tiny bit taller in a field of greatness…

The Steve McQueen Explorer II, reference 1655

Evidence that Hollywood legend Steve McQueen actually wore this Explorer II is as thin on the ground as proof of extra-terrestrial life. Yet the myth, if that’s what it is, persists. Still, even if this watch never adorned McQueen’s wrist, it should have. The dial is 70s-era funky, the bezel is pared-down perfection and the Italians even gave it an affectionate nickname: “Freccione” (“Big arrow”).

James Cameron Sea-Dweller Deepsea, reference 126660

If the 300-metre water resistance of a Submariner isn’t enough to reassure you when wrist-deep in washing-up, consider instead the beefy Sea-Dweller Deepsea. This is the civilian version of the prototype worn by film director James Cameron when he made his famous descent to the bottom of the ocean. Water-resistant to 3,900 metres, its crystal alone is the thickness of the average dress watch.

John Mayer Daytona, reference 116508

While the “Paul Newman” Daytona is a clinically cool, steel sports watch, the more contemporary “John Mayer” Daytona radiates rock glamour. The most striking thing about this discontinued model is not the yellow-gold case and bracelet but the drool-worthy dial. With its jade-green hue and red-accented subdials it’s a watch so mesmerising it could be used for hypnosis. Pure collectors’ catnip.

The first Submariner with date, reference 1680

Once upon a time, the trusty Submariner came minus a date function. Then, in 1966, Rolex launched the stalwart 1680, adding a date window beneath its now signature Cyclops lens. The 1680 had a healthy lifespan, rolling off the Rolex production line for 15 years or so before it was discontinued. Vintage models of this greatly admired Rolex tool watch are plentiful today.

Rolex “Paul Newman” Daytona, reference 6239

Image courtesy of Phillips

Image courtesy of Phillips

There is no single “Paul Newman Daytona”. His wife Joanne, clearly struggling with gift-buying ideas for the man who had everything, bought him at least two during their lengthy marriage, engraving the casebacks with requests that he “drive slowly” when indulging his love for motor-racing. However, the 6239 is the model he’s synonymous with, and the one that went stratospheric at auction, selling for $17.8 million in 2017.

First ever quartz Rolex, reference 5100

Image courtesy of Phillips

Image courtesy of Phillips

Mechanical devotees who treat battery-powered watches as if they were spreaders of ebola might soften their stance for this historic Rolex. Launched in 1970 using the Beta 21 movement—produced by a consortium of Swiss brands in response to Japanese quartz watches—this was the first quartz Rolex and the first with a sapphire crystal. Only a thousand models were made, selling out before delivery.

Marlon Brando’s personal Rolex GMT-Master

Image courtesy of Phillips

Image courtesy of Phillips

Could a watch be more symbolic than the broken Rolex worn by Marlon Brando in Apocalypse Now? Shot on location in Vietnam, the film was besieged by production problems, with actors dropping out and losing their sanity. So the fact that Brando wore his own damaged GMT-Master 1675 with a missing bezel is apt. The bezel was never found, but it still sold for nearly $2m at auction in 2019.

SARU GMT-Master II, reference 116758

In ancient times, wearing rubies was thought to counteract the effects of poison, while sapphires were thought to exude heavenly rays. If this were true it would make any SARU wearer a kind of Marvel superhero. Boasting 23 diamonds, 18 sapphires and 18 rubies on the bezel, as well as 76 diamonds on the case, it’s unrivalled in the rarefied world of gem-set Rolexes.

Submariner “Cookie Monster”, reference 126619LB

Silliest Rolex nickname ever? Probably, but this handsome Submariner in white gold is a stealth-wealth classic. Some people think a dive watch made of precious metal is contradictory (admittedly, you wouldn’t wear one while welding oil rigs under the sea). But there’s something seductive about a white gold watch with sporty looks. And that black dial and blue bezel combo is superb.

The Gerald Genta Rolex, reference 3580

Image courtesy of Bonhams

Image courtesy of Bonhams

The award for the most un-Rolex Rolex goes to the King Midas, designed by the legendary Gerald Genta and owned by Elvis Presley, among others. With its asymmetric 18k gold case and a chunky bracelet that looks as though it was fashioned out of solid ingots, this was the heaviest watch of its era and the most expensive Rolex money could buy back in the mid-1960s and early 1970s.

Mercedes Gleitz’s Rolex Oyster

This was the timepiece that not only cemented Rolex’s place among watch industry innovators but epitomised the marketing genius of brand co-founder Hans Wilsdorf. Having devised the first waterproof watch, he persuaded record-breaking endurance athlete Mercedes Gleitz to wear it when swimming the English Channel in 1927. He then proclaimed the amazing feat via a front-page newspaper advert.

“Rainbow” Daytona, reference 116598

Here’s another ultra-rare gem-set Rolex that you’ll rarely see in the wild—unless you hang out with millionaire rap moguls or live in Dubai. This dazzling gold Daytona features a 36-sapphire “Rainbow” bezel, with chronograph subdials made from a twinkling blend of gold and crystal. It’s not hard to see why this grabbed the headlines when it literally lit up Baselworld in 2012.

Sky-Dweller—the “business man’s watch”

New Rolex collections occur about as often as a change of pope, and with nearly as much fanfare. Indeed, when the Sky-Dweller debuted in 2012 it was the brand’s first new series in 20 years. And the Crown really did up its game with this one, bringing us a second time zone and annual calendar, ingeniously controlled via the fluted bezel. Dressier than a GMT-Master, this watch comes in gold, or gold and steel.

Rolex Cellini Cellinium, reference 5241

You killed the Cellini. Yes, you, the watch-buying public. Rolex discontinued its long-running dress line in 2023 because it got as much love and affection as a rabid stray dog with mange. You’ll miss it now that it’s gone, though. Or maybe you won’t, because some of the designs were a bit dull. But for the discerning, Cellini-appreciating minority we’ve included this manual-wind stunner in platinum.

James Bond’s Submariner, reference 6538

Image courtesy of Bonhams

Image courtesy of Bonhams

Forget Omega, Rolex is home to the original Bond watch. View any of the first four 007 films and you’ll see Sean Connery’s Bond sporting the Submariner reference 6538 “Big Crown”, known for its, you guessed it, enlarged crown. Thanks to the Bond effect, the Submariner boomed in popularity, with everyone from accountants to actors trying to channel their inner 007.

The “Bao Dai” moonphase, reference 6062

Image courtesy of Phillips

Image courtesy of Phillips

We wish we had the status, wealth and audacity to approach Rolex demanding their rarest piece, just like the Last Emperor of Vietnam, Bao Dai, did. After declining several watches, he decided on this yellow-gold reference 6062 with moonphase display. In 2002, it became the most expensive Rolex sold at the time, fetching 370,000 CHF at auction. Steel and rose-gold versions were also made in small numbers.

Dato-Compax “Jean-Claude Killy”, reference 6036

Image courtesy of Bonhams

Image courtesy of Bonhams

Ever seen a Rolex with this many buttons and pushers? This complex timepiece boasts a chronograph and a triple calendar and was one of many chronographs Rolex produced before the Daytona emerged as the only watch in the Crown’s line-up to boast this function. It was named the “Jean-Claude Killy” after the French Olympic ski champion, a Rolex brand ambassador. Models now fetch six-figure sums at auction.

The 1908, reference 52508

We knew something was afoot when Rolex began slowly phasing out the Cellini, its long-running dress watch series. We also knew that it wasn’t going to head in an entirely new direction with whatever replaced it. Sure enough, the brand-new 1908 appeared in 2023 and delivered all the shock of a snowy day in Siberia. Radical it ain’t, but it is one of the most elegant Rolexes around and scrapes into this list.

The quintessential vintage GMT-Master

If you enjoy dressing up as a 1950s Pan Am pilot, the vintage GMT-Master 1675 is the perfect accessory. When Rolex aficionados think of a vintage GMT, this model in steel with the “Pepsi” bezel springs to mind, boasting the longest production run of any watch in Rolex’s catalogue. During this time it underwent some minor superficial changes, resulting in several slightly varying models, all of which continue to woo collectors.

The “Destro” GMT-Master II for lefties, reference 126720VTNR

When this watch got released at Watches & Wonders 2022, two debates dominated online watch forums. Firstly, is this another Rolex marketing ploy? And secondly, what frivolous nickname will it be lumbered with? We’re still not sure about the former; as for the latter, the “Sprite” seems to have stuck—much to the chagrin of the adults in the room. It still looks cool, though.

The “quartz-style” Oyster Perpetual True Beat, reference 6556

Image courtesy of Bonhams

Image courtesy of Bonhams

Ever wanted a mechanical Rolex that ticks like a quartz? The rare Tru-Beat 6556 from the 1950s does just that with its “dead beat” seconds hand, foregoing the usual sweeping motion found on mechanical watches. Targeted at medical professionals to help them calculate a patient’s pulse rate, it was too far ahead of its time and got discontinued after a blink-and-you’ll-miss-it production run.

The classic fluted-bezel Datejust, reference 126234

Timeless, unisex and versatile enough to wear with anything, the Datejust is the watch you buy as a family heirloom so that your descendants can look as stylish as you. Take a look at the first-generation model from 1945 and it’s reassuring to see that it has changed little over the decades. We’ll happily settle for any steel and white gold model with a fluted bezel and a jubilee bracelet, like this reference 126234.

The Air King 126900

Since its debut in 1945 the Air-King has undergone more cosmetic tweaks than Michael Jackson. Early versions were barely distinguishable from the humble Oyster Perpetual before Rolex began jazzing it up with engine-turned bezels and concentric dials. This current version arrived in 2022, six years after it was given a total revamp with the 116900. We think they’ve finally nailed it with this one. Can the meddling stop now, please?

The Dalai Lama’s Day-Date

Buddhists care little for material wealth but that hasn’t stopped the Dalai Lama wearing a top-tier Rolex. His yellow-gold Day-Date features a lapis lazuli dial whose intense blue colour is significant as it is said to represent heaven and spiritual insights in Tibetan Buddhism. It’s reported to be a gift, not a purchase—not that we can imagine the Dalai Lama having to be put on a Rolex waiting list.

The Everest Rolex

The success of the Explorer stems from its association with the Everest expedition of 1953 when Rolex equipped the team with watches that could cope with the freezing temperatures of the Himalayas. Debate rages over who wore what or whether a Rolex even reached the mountain’s summit—the British company Smith’s also supplied the expedition with watches—but the Crown has alluded to the feat in its adverts many times since.

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