The Weirdest Rolex Watches Of All Time

The craziest pieces from the Crown.

The Weirdest Rolex Watches Of All Time

Image: Romer Macapuno/DMARGE

Rolex, the world’s biggest watch brand and easily the most coveted, makes millions of watches a year, most of which are pretty conventional. But the 119-year-old firm has also made more than a few wacky pieces over the years, too. Here are some of the weirdest.

Even people who don’t know anything about watches know a bit about Rolex. It’s arguably the world’s best-known luxury brand: its watches are a byword for success. Models like the Daytona, GMT-Master and Submariner have cemented themselves as bonafide pop culture icons thanks to being seen on the wrists of the world’s rich, cool and famous.

Of course these days it can be nearly impossible for fans to get their hands on the latest Rolex pieces, with limited availability only adding to the brand’s enduring appeal. The secondary market is also having a crazy effect on Rolex prices.

It’s easy to forget but Rolex is such a big name today because they rank as one of the most innovative watchmakers in history – and their decades of experimentation have also seen some properly bonkers watches come out of their Swiss factories…

We’ve rounded up a few of the most historically significant and unusual Rolex watches ever made for your viewing pleasure.

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Rolex Cellini King Midas

Image: Hairspring

First up, we have the Rolex Cellini King Midas, which – with its asymmetrical, polygonal case and sleek integrated bracelet – is quite unlike any other Rolex watch ever made.

Part of Rolex’s Cellini dress watch line, the King Midas was designed by the legendary Gérald Genta (who also designed the Audemars Piguet Royal Oak and Patek Philippe Nautilus) and, as the name implies, was inspired by the famous Greek legend of the same name.

Appropriately, when it was introduced in 1964, it was the heaviest gold watch on the market, as well as the most expensive Rolex of its time.

The King Midas has always had a bit of a following among well-heeled celebrities. John Wayne wore a King Midas, as did the King of Rock n’ Roll himself, Elvis Presley. Christopher Lee also wore a King Midas in his role as James Bond villain Francisco Scaramanga in The Man with the Golden Gun (1974).

In more recent times, the King Midas has been worn by pop superstar Rihanna, as well as by singer/songwriter The Weeknd.

Rolex Day-Date ‘Tridor’

Image: Bob’s Watches

At first glance, the Rolex Day-Date ‘Tridor’ looks like just a normal two-tone Day-Date – but those in the know, know that Rolex only ever makes the Day-Date in either gold or platinum, reflecting its status as Rolex’s flagship luxury watch. So what’s going on here?

Well, ‘Tridor’ is Rolex’s name for a combination of three types of gold: yellow, rose and white gold (just as they call their proprietary combination of steel and gold ‘Rolesor’). As you can see, the centre link of the watch’s President bracelet features those three metals fused together in perfectly straight lines running through the entire length of the bracelet – an impressive display of metalworking.

So while it looks like it might be two-tone stainless steel and gold, the case of the Day-Date ‘Tridor’ is actually made of white gold, and its bezel is made of yellow gold. Anyhow, it’s an incredibly unique-looking Rolex. Unsurprisingly, this watch was introduced in the 1980s.

The most famous person to ever wear a Day-Date ‘Tridor’ was legendary golfer Arnold Palmer, a lifelong Rolex wearer and the first official Rolex golf ambassador. Rolex discontinued Tridor a long time ago, but with all things golf having a moment right now, could we see Tridor make a comeback?

WATCH our guide to the most expensive Rolex watches ever sold at auction below.

Rolex Air-King ‘Domino’s Pizza’

A slice for the wrist. Image: Analog:Shift

The so-called ‘Domino’s Air-King’ is one of the best-known pieces of Rolex folklore and stands out as one of the most incongruous Rolex watches ever made.

Ever since 1977, the international fast-food chain has given out Domino’s-branded Air-Kings to store managers to who hit $30,000 per week for four consecutive weeks in sales, among other requirements. Naturally, this weird collaboration between a luxury brand and a pizza chain has given these watches a cult status.

Strictly speaking, while most examples are Air-Kings, after Rolex briefly discontinued the Air-King back in 2014, Domino’s switched to giving out Oyster Perpetuals – with those watches featuring unadorned dials and instead boasting bracelets with a unique Domino’s centre link.

In recent years, Domino’s has continued to raise the threshold for the reward (it used to be $10,000 per week, for example) so there are fewer of these oddball Rolexes getting given out. Still, if you’re looking for a Rolex that’s a bit different, there are plenty of these out in the wild for sale…

Rolex Day-Date ‘Jigsaw’

This has become a favourite for NFL GOAT Tom Brady. Image: Rolex

Last year at Watches & Wonders Geneva 2023, Rolex decided to get a little silly and released one of the kookiest watches they’ve ever made: a kaleidoscopic take on the Day-Date that’s really polarised watch fans.

Not only do these Day-Date ‘Jigsaws’ feature garish enamelled dials with multicoloured jigsaw piece motifs, but they also feature rainbow-coloured gemstones for hour markers. It looks like a kid’s playroom and if it wasn’t weird enough, the day and date windows now display “an inspirational keyword” and one of 31 different emojis instead of days of the week or numbers.

Rolex says that “by displaying a new emotion each day, the watch brings an element of spontaneity into the wearers’ daily life and allows them to invest the reading of time with their changing mood.” We think it’s weird as hell – but we also like the fact that they decided to do something weird this year rather than release yet another subtle tweak to an old design. Stars like Tom Brady also seem to agree, after the NFL GOAT was spotted wearing one whilst he watched one of his investments play football.

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Rolex Pearlmaster

Who doesn’t like a bit of bling? Image: The Watch Club

Another similarly less-than-subtle Rolex is the Rolex Pearlmaster. Based on the Datejust and generally only available in ladies’ sizes, the Pearlmaster is exclusively crafted from precious metals and always adorned with gemstones (and not pearls, rather confusingly, although some have mother-of-pearl dials…)

The Pearlmaster name actually comes from the watch’s unique bracelet design, which features rounded five-piece links and a concealed clasp – and is only found on the Pearlmaster.

While the Pearlmaster has always been positioned as a ladies’ piece, a few male celebrities have been spotted rocking the excessively opulent Rolex over the years, such as LeBron James.

Rolex Milgauss Green Crystal

Image: Chronoautix

At the same time that Rolex introduced the Day-Date ‘Jigsaw’, they also discontinued one of the lowkey weirdest and most underrated watches in their repertoire: the often-overlooked Milgauss. Rolex gives with one hand and taketh with the other, I suppose.

Originally launched in 1956, the modern incarnation of the anti-magnetic engineer’s watch is particularly odd, with its green-tinted sapphire crystal, fluoro-coloured highlights, double caseback and lightning bolt-shaped seconds hand, which really made it really stand out amongst Rolex’s sometimes rather sober range. That green crystal in particular is super weird.

Maybe it’s because the modern Milgauss was such an oddball that Rolex decided to retire it. My theory? They’ll bring it back in 2026 for its 70th anniversary.

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Rolex Datejust Turn-O-Graph

The first pilot watch from Rolex. Image: Crown & Caliber

Another surprisingly strange watch from Rolex’s back catalogue is the Datejust Turn-O-Graph: the first-ever Rolex watch to feature a rotating bezel, predating the GMT-Master and Submariner, and therefore the first-ever modern Rolex tool watch.

First introduced in 1953, the Turn-O-Graph took Rolex’s iconic fluted bezel and made it functional by adding 60-second markers – a rather unique look. Rolex wouldn’t introduce another functional fluted bezel on a watch until 2012 with the Sky-Dweller.

The Turn-O-Graph, aside from being Rolex’s first tool watch, was also the first Rolex pilot’s watch and saw military use by the US Air Force’s ‘Thunderbird’ aerobatic squadron. Rolex capitalised on the association and began referring to all Turn-O-Graph watches in the American market as ‘Thunderbirds’, even producing a model with the squadron’s insignia.

After a long period of discontinuation, Rolex reissued the Turn-O-Graph in the 2000s, retiring the model once more in 2011. To this day, not many people know about the Turn-O-Graph, despite its historical significance.

Rolex Cosmograph Daytona ‘Leopard’

The Crown adds some colour. Image: Rolex

This might take the cake for the ugliest watch Rolex has ever made. Rolex has made more than a few outlandish ‘off-catalogue’ Daytonas over the years, but the Daytona ‘Leopard’ is particularly mental.

This reference sees the normally clean and stylish Daytona outfitted in yellow gold with diamond hour markers, diamond set lugs and 36 cognac-coloured sapphires adoring its bezel in place of the usual tachymeter scale. But wait, there’s more: the dial features a leopard-print motif, and it comes mounted on a leopard-print leather strap.

What more can we say about this one? It’s an eyesore, but again, we kinda like the fact that Rolex was bold enough to make it. Naturally, it’s been spotted on the wrist of some pretty out-there celebrities, including the walking meme that is Nicolas Cage and Aerosmith’s Steven Tyler.

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Rolex Deep Sea Special

Rolex’s deep sea dial. Image: Phillips

Finally, we have the Deep Sea Special (and a personal favourite). This watch was designed by Rolex in the 50s with one mission in mind: to get to the bottom of the ocean. Allegedly, only five functional prototypes were ever made, one of which was attached to the outside of the legendary bathyscaphe Trieste when it became the first crewed vessel to reach the bottom of the Mariana Trench’s Challenger Deep, the ocean’s deepest point, in 1960.

The Deep Sea Special is easily the most unusual and least ergonomic timepiece Rolex ever made. Not only does it feature a mammoth 42mm x 62mm case, but its incredibly domed plexiglass crystal – extra-thick to withstand immense pressures – is almost taller than the case is wide.

Examples of the Deep Sea Special rank as grails among grails for Rolex aficionados. Deep Sea Special #3, the watch that was actually used on the record-setting Challenger Deep dive, is currently housed at the Smithsonian, while a few exist in the wild – although many have a rather murky provenance, as Perezscope elaborates.