This Watch Is Beloved by John Mayer, Michael Jordan, Jonah Hill, and Jay-Z

This Watch Is Beloved by John Mayer, Michael Jordan, Jonah Hill, and Jay-Z

Some watch collectors are omnivorous, grazing from across the landscape of brands, models, and types of pieces. Others hunt down pieces in a single genre: racing, pilots, or divers watches. Others still obsess over buying the very best from a single brand. But there are also a few very special models that, entirely on their own, beckon hordes of collectors. The Rolex Cosmograph Daytona—which comes in stainless steel, set with a rainbow of sapphires, in platinum, with exotic dials, and 18-carat yellow gold, and so on—is one of those watches.

As Hodinkee founder Ben Clymer recently wrote in an ode to chronograph watches in GQ, “these three [the Daytona, the Omega Speedmaster, and the Heuer Carrera] represent entire categories of collecting and scholarship unto themselves, and over the past seven decades they have rightly reached a level of appreciation that in some cases surpasses even the brands that produce them.” The Daytona is the ultimate crown jewel: it’s given as a prize to the winner of the 24 Hours at Daytona race, and Jay-Z used it as an invite for VIPs to his gala. And it smashes records: in 2015 it became the most expensive Rolex ever when Eric Clapton’s former “Oyster Albino” sold for $1.4 million, and it broke the record for most expensive watch ever in 2017 when Paul Newman’s went for $17.8 million. Below, collectors like Michael Jordan, John Mayer, and Jay show the full breadth of the beloved Daytona.

Courtesy of Hot Ones

John Mayer’s “Rainbow” Daytona reference 116598

In the second installment of John Mayer’s “Talking Watches” video with Hodinkee, he talked through 11–eleven!—Daytonas! This one, with a rainbow of 36 sapphires, may not fit exactly with the model’s traditionally sporty lineage, but damn, is it fun. “I don’t quite know who the target audience is if you’re looking at the aesthetic,” Mayer said in the video. “When these first came out everyone thought they were too much. The attitude on a Rainbow Daytona when they first came out was ‘Yuck. Who would do that? Who would go so far?’ Something happened that’s brilliant where the joy of collecting superseded the craziness of the design of these watches.” Mayer, of course, didn’t think they were too much. He brought multiple diamond- and sapphire-set Daytonas to the table and cops to wearing them frequently.

Kent Smith SwissLuxury.Com 2004-2013

Michael Jordan’s 50th-anniversary edition, reference 116506

In 2013, expectations were high for what Rolex would cook up to commemorate the Dayton’s 50th anniversary. The result is this very unexpected but elegant version of the Daytona: the very first in platinum, with an ice-blue dial and chocolate-y bezel. It makes sense that Michael Jordan, who seems hellbent on scouring the earth for the strangest timepieces in existence, would make this very special oddball part of his rotation.

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Jonah Hill’s “John Mayer” Daytona reference 116508

Hill’s gold-and-green Daytona is a microcosm of the watch world’s peculiarities. When it debuted at the watch tradeshow Baselworld in 2016, the model was relatively unloved. Unlike nearly every other Daytona model in existence, it sat in jewelry cases with its $34,650 pricetag. But when it comes to watch value, it takes only one person to shift the gravity. Following a Mayer shoutout in the Hodinkee video above, collectors suddenly started paying closer attention to the piece. The singer had such an effect on the watch that people started calling it the “John Mayer” Daytona, and collectors are now paying upwards of $50,000 for it on the secondary market.

Jason Miller

Jay-Z’s reference 116500LN

When Jay-Z wore this watch to the 2016 NBA Finals, it was the likely the hottest piece in the entire collecting community. After the flashy and unconventional platinum version released in 2013 disappointed scores of Rolex fanatics, this version was a balm. In 2016, Rolex released another round of new Daytonas—and, finally, here was a watch in stainless steel that faithfully recreated a vintage version with a black-and-white “Panda” dial.” This Daytona frustrated collectors with its multi-year waitlist. Of course, that wasn’t a problem for Hov.

Courtesy of the Geoffrey Hewitt Photograph Collection Courtesy of Philips

Paul Newman’s “Big Red” Daytona reference 6263

While Newman is most famous for the exotic-dial Daytona that is now named after him (and went for nearly $18 million at auction), that wasn’t the only version of the model he wore. After he gave that Daytona to his daughter’s boyfriend, he picked up this “Big Red” version—named for the slightly fatter arch of text over the center subdial. This watch has a lot in common with Newman’s original: after two years, he passed this watch down to his daughter. Like the first, it has a sweet inscription from his wife on the caseback that reads “Drive Slowly Joanne.” And this watch is also coming to auction and is expected to demand a huge amount of cash. Phillips, the auction house selling the watch, simply estimates it will go for somewhere “in excess of $1 million.”

Michael Stewart

Ed Sheeran’s “Paul Newman” Daytona reference 6239

Of course, no discussion of the Daytona would be complete without talking about the reference 6239: the most famous of all Daytona models and is the version of the watch that really put the timepiece on the map. Because of its garish design and out-there art-deco text, the legend goes, the watch was initially a poor seller upon its original release in the early ‘60s. Low sales meant that Rolex produced very few of the watches, which only makes them that much rarer today. The 6239 is exactly the type of watch that a freakishly devoted collector like Sheeran would absolutely have to have. He even wears his on a leather bund strap, exactly the way Paul Newman did.

Rolex watches with ageless value to invest in today

Aside from their great looks and topnotch performance, a significant appeal of Rolex watches is their ability to hold their value better than watches from almost any other brand, writes Paul Altieri, founder and CEO of Bob’s Watches, one of the most respected traders of pre-owned luxury watches in America.

While resale value should never be your main priority when buying a luxury watch, it certainly is a bonus.

Although it must be said that not all Rolex watches appreciate in value, some certainly do — particularly over the long run. With that in mind, let’s explore the ageless value of Rolex watches with some of these top hits.

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Yellow Gold Rolex Day-Date President

Nicknamed the Rolex President thanks to its President bracelet and its popularity among some of the world’s most powerful individuals, the Day-Date has been the ultimate status symbol watch since its inception over six decades ago.

While the Rolex President is offered in a variety of precious metals and sizes, along with various bezel styles and dial designs, the classic choice is a yellow gold 36mm model with a fluted bezel and champagne dial.

A more recent iteration is this Day-Date 36 ref. 118238 from the mid-2000s, which features the archetypical Rolex Presidential style yet includes modern enhancements such as a sapphire crystal, Super-LumiNova, and the automatic Caliber 3155 movement with Double Quickset functionality.

Due to its precious yellow gold construction and enduring appeal, this President timepiece perfectly demonstrates the ageless value of Rolex watches.

Men’s Rolex Day-Date President in Yellow Gold – $16,495 on Bob’s Watches

Stainless steel Submariner

When it comes to premium diving watches, there’s no other model that is as coveted and recognizable as the Rolex Submariner.

Born in the 1950s as a tool watch for scuba divers and eventually evolving into a luxury sports watch with fantastic diving capabilities, the Submariner is popular amongst celebrities, collectors, and casual watch buyers alike.

Over the years, Rolex has made a bevy of different Submariner models in a variety of materials and colors. But for purists, the go-to Submariner is a stainless steel one with a black dial and black bezel – similar to the earliest models.

The current-production Submariner ref. 116610LN combines the unmistakable look of a classic Sub but packed with contemporary features like a scratch and fade resistant Cerachrom ceramic bezel, blue glowing Chromalight luminescence, and an updated Oyster bracelet complete with the Glidelock extension system.

And because this is a Submariner Date model, there’s also the familiar date window (complete with Cyclops magnification lens), powered by the in-house Caliber 3135 automatic movement. On the secondary market, the Submariner ref. 116610LN frequently sells above its retail price due to its demand far outpacing the current supply, despite the model now being a full decade old.

Men’s Rolex Submariner in Stainless Steel – $10,395 on Bob’s Watches

Stainless Steel Rolex GMT-Master II “Pepsi”

The GMT-Master also made its debut in the 1950s, developed specifically for Pan Am airline pilots to keep track of two time zones while on the job. Rolex made the very first GMT-Master watch in stainless steel and equipped it with a blue and red bezel to divide the 24 hours of the GMT indication into day and night hours.

That colorway eventually picked up the “Pepsi” nickname and despite other color choices, the blue and red combo became the quintessential look for the Rolex GMT.

So when Rolex unveiled the brand new stainless steel GMT-Master II ref. 126710BLRO “Pepsi” in 2018, there was no doubt that it would become a mega success, and continues to be a popular choice on the used secondary market.

Sporting a 40mm stainless steel case, a matching stainless steel Jubilee bracelet, “Pepsi” Cerachrom ceramic bezel, and powered by the new-generation Caliber 3285 automatic movement boasting major performance improvements, this is the model that brings the GMT-Master squarely into the 21st century.

And judging by its exceptional current demand and price point on the secondary market, this is one Rolex model that will likely hold on to its value for the foreseeable future.

Men’s Rolex GMT Master in Stainless Steel – $15,995 on Bob’s Watches

Yellow Gold Rolex Daytona

For the majority of its models, Rolex typically adheres to a fundamental design blueprint, which explains why so many of its watches are instantly recognizable, regardless of what era they were manufactured.

However, the Daytona chronograph is one that has evolved quite dramatically since its introduction in the 1960s.

Once a smallish manual-winding chronograph that never really took off during its time, to today’s perfectly-proportioned modern automatic luxury chronograph, the Rolex Daytona now stands out as the most famous model of its genre.

While stainless steel and ceramic Daytona references are unquestionably prized, there’s another, more lavish take on Rolex’s flagship chronograph that’s become the must-have model in recent years.

That’s the unapologetically opulent, yellow gold Rolex Daytona ref. 116508 with a brilliant green sunburst dial.

Solid yellow gold Rolex watches have always been ageless; but when we’re talking about a yellow gold Daytona paired with a dial in the brand’s signature green hue, the appeal is amplified. Forget being a future collectible; the four-year-old Rolex Daytona ref. 116508 is already a collectible right now.

Men’s Rolex Daytona in Yellow Gold – $44,995 on Bob’s Watches.

Men’s Rolex Datejust 41 in Stainless Steel

Often described as the quintessential Rolex watch, the Datejust has been around since 1945 and continues to be the brand’s mainstay model.

With its straightforward time and date dial, round Oyster case, and robust automatic movement, the Oyster Perpetual Datejust is the ideal luxury watch to wear just about all the time.

Although the Datejust comes in a vast assortment of metals, styles, and sizes, one of the best picks currently is the Datejust 41 ref. 126300 in stainless steel.

The Datejust 41 is a relatively new collection, first launched in 2016, and it has everything you’d want from the classic 36mm Datejust but in a larger, more contemporary size.

The minimalistic approach of a steel case, steel Oyster bracelet, silver dial, and smooth bezel is not only ideal for daily wear, but it will continue to look as fresh for decades to come.

Positioned as one of the leading luxury brands in the world thanks to a collection of iconic designs paired with topnotch technical performance, the ageless value of Rolex watches is one that has been in the making for over a century.

A Rolex Daytona Has Watch Collectors Green With Envy

The economy may be exhibiting signs of a slowdown, but prices for luxury watches continue to soar.

Take the gold Rolex Daytona 116508. Like all of its Daytona forebears, it is a mechanical cosmograph that functions as both timekeeper and glorified stopwatch, with three subdials that racecar drivers can use to measure distance and speed.

Although it can be ordered with champagne-colored or black dials, the current frenzy is centered around an iridescent green version. Authorized dealers are sold out, and prices on the secondary market have exceeded $50,000 — seemingly a record for the brand. (The list price is $34,650).