There is no shortage of A-listers who have bought a Rolex or two. It’s basically a right of passage for the super rich at this point. But for some of them, collecting Rollies has grown into something of an obsession.
John Mayer. Jay-Z. Brad Pitt. Roger Federer (who’s actually been an ambassador for a quarter of a century, but more on that later). Between those four alone, you’re looking at watch hauls that span everything from a Daytona ‘Paul Newman’ grail to the kind of timepieces you’d only come across in a Christie’s auction.
Prestige aside, they’re the kind of watches you could wear with pretty much any outfit to anything you’ve got in the diary. On the red carpet at the Met Gala. In the front row at a fashion show. Or even when you’re lifting your 20th Grand Slam trophy – as you do.
So, it’s no wonder these guys have curated some of the most impressive Rolex collections in the world. Let’s take a closer look at their best pieces and see exactly what makes each one tick.
John Mayer: The Watch Nerd
Let’s start with John Mayer, one of the most respected celebrity watch collectors in the world. Once you see his Rolex line-up, you’ll understand why. It’s less about flashy models and hypey references – even though he does have a white gold Rainbow Daytona (ref 116599RBOW​​) that’s going for more than £200k on Chrono24 – and more about the silhouettes that matter.
Rolex Cosmograph Daytona ref 116508
Vintage ‘Paul Newman’ Daytonas, namely the 6263 in yellow gold, a 6264 with a Panda dial and the 6240, the tri-colour design which is also known as the 3CROC. The most coveted GMT-Masters – he’s got both the Batman, with its black and blue bezel, and the Pepsi, which swaps black for red. And even the OTT Smurf Submariner with its punchy blue dial and matching bezel.
Basically, it’s a carefully curated selection that’s full of some of the most coveted Rollies going. So, it’s only fair that one of the crown’s models is now widely referred to as the ‘John Mayer’ (the Cosmograph Daytona ref 116508 with a green sunburst dial which he named a ‘sleeper hit’ in a 2019 interview) – a nice full circle moment, seeing as his first ever ‘proper’ watch was a Submariner which he bought following the success of his album Room for Squares in 2001.
Jay Z: The Big Time Flex
Jay-Z’s collection is more about flexing the rarest, most hyped Rolexes in the world – in fact, it’s estimated to be worth nearly $6.5 million (roughly £5 million).
His most valuable is the Daytona ref 6270 ‘Sultan of Oman’, a highly sought-after model from the mid-1980s which was made for Sultan Qaboos bin Said al Said of Oman. It’s the brand’s first ever gem-set Daytona and there’s only 8 in existence (which were all created for the Sultan and his inner circle). So, it’s no surprise that it costs around $4 million.
Rolex Daytona ref 6270 ‘Sultan of Oman’
His rare investments don’t stop there – he also has a Daytona 6263 ‘Tiffany’ which has a Paul Newman dial and a co-signed Tiffany & Co. stamp, meaning the watch was originally sold through the New York jeweller. Then there’s the Day-Date 40 ref 228206, a 950 platinum model with an ice blue sunburst dial and Eastern Arabic numerals (it was originally produced for Middle Eastern markets).
In short, if it’s not limited edition or worth at least $800,000, it’s probably not going to be anywhere near Jay Z’s wrist.
Brad Pitt: The King Of Classics
Though Brad Pitt is undoubtedly a fan of Rolex, his collection is full of low-key classics rather than anything ultra-rare.
A stainless steel Daytona ref. 16520 – a reference that’s powered by the iconic Zenith El primero movement which was one of the first automatic, integrated column-wheel chronograph movements – or an 18k yellow gold Rolex Yacht-Master 40 ref 16628 which he wore for a photoshoot in the late nineties, for instance.
He’s partial to a watch on screen, too. The pieces he wore as con-artist Rusty Ryan in the Ocean’s Eleven franchise, which are believed to be from his own stash, included a couple of understated Rollies. In the first film, he wore a two-tone ‘Rolesor’ Submariner which he swapped with a platinum Day-Date ref 118366 in the sequel.
So, for a two-time Academy Award winner who’s one of the highest grossing actors of all time, his taste in Rolexes is fairly modest (which is why we’re big fans).
Roger Federer: The Gold Standard
As a brand ambassador for over 25 years, Roger Federer has worn a Rolex to nearly every public appearance since 2001 – whether it be at post-match press conferences, the Met Gala or even when he’s sitting in the crowd at Wimbledon. And, more often than not, they’re always the iconic silhouettes that come with clout. An Oyster Perpetual. A Day-Date. Even a Wimbledon-inspired Datejust. The type of watches every guy would want in their collection.
Rolex DateJust 41 ’Wimbledon’ ref 126333
Don’t get me wrong, though: he doesn’t always play it safe. His set includes gem-set Daytonas (the Daytona ‘Orange’ ref 116588SACO or the sapphire-encrusted ref 126599TSA), a bright green Oyster Perpetual 41, and even an XL Yacht Master II which he wore to lift the trophy for the French Open in 2009.
So, he clearly knows his Rolexes – the OG classics speak for themselves – but he’s willing to experiment with the statement references, too.
