Drake’s New Rolex Is a True-Blue Grail

Welcome to Watches of the Week, where we’ll track the rarest, wildest, and most covetable watches spotted on celebrities.

Maybe no one attacks watch collecting more voraciously than Drake, who is seemingly up to dive into every corner of the watch world. He’ll wear a Patek Philippe customized by Virgil Abloh one day, a horny Richard Mille another, and keep you on your toes by citing Queen Elizabeth II as the inspiration for wearing a rare version of a Patek Philippe Ellipse. Last weekend, he wore a watch with less complicated bona fides: the Rolex Daytona “Paul Newman,” famously one of the watch world’s most important grails. For a guy who’s done a whole lot of watch flexing, this might be his most impressive flex yet.

For the uninitiated, the watch got its name because Paul Newman wore this style of Daytona. Simple enough! But the actor’s endorsement was a big deal: before photographs of Newman wearing this watch spread, this model was unloved by most collectors. And then, all of a sudden, it wasn’t. The watch comes with some funky features, like an “exotic” dial that features a sunken outer edge in different color than the center and those jaunty numerals on the subdials. These details once scared collectors away—but they’re the same ones that make this watch one of the hobby’s holy grails in 2023. 

The “Paul Newman” Daytona is an interesting choice for Drake, who breaks a lot of the conventional rules when it comes to watch collecting. He let Abloh cover his Nautilus in diamonds, and frequently trades out the standard bracelets on Rolex watches with ones from Chrome Hearts, flouting the conventional wisdom that says changing out anything on a watch once it leaves the factory is a huge no-no. The Daytona “Paul Newman,” on the other hand, is a true nerd’s grail. It’s a watch that requires the buyer to understand the details that make it special. (If you want to be cynical, you can argue Drake is simply buying into the enormous hype around this piece. Paul Newman’s very own “Paul Newman” Daytona sold for $17.8 million, briefly setting a record for most expensive wristwatch ever, in the fall of 2017, while most run for around $TK.) 

Drake’s new Daytona might not have belonged to Newman, but it does have a special connection to the rapper. Menta Watch’s Adam Golden, who sourced this piece, explained in an Instagram comment that “this one came straight out of the original owner from Toronto.” I don’t know if he’s ever mentioned this, but Drake is actually from Toronto. Pretty cool coincidence. 

Jeremy Allen White’s Vacheron Constantin 222 

It turns out that Jeremy Allen White and I have plenty in common. He plays a tortured chef on The Bear, a perfect show with perfect white T-shirts. I’m also extremely passionate about both food and tees. He had a meal at Langer’s, Los Angeles’s home for killer pastrami, last year; so did I. (Technically this was because we were there at the same time, to conduct an interview for GQ’s Men of the Year issue, but I’d argue it’s also because we both love pastrami. He was a delight, in case you’re wondering.) Now, at this year’s Critic’s Choice Awards (where the critics get to choose!), he outs himself as a watch nerd. More than that: his VC 222, a revival of the brand’s sporty watch from the ‘70s, was near the very top of my list of favorite 2022 releases. I feel like this is that scene in Step Brothers: “Did we just become best friends?” “Yup.” 

Steph Curry’s Rolex Deepsea Sea Dweller 

Sport watches have taken over as the dominant category when it comes to watch collecting. These tough stainless steel pieces are now acceptable for romantic date nights, red carpets, and business meetings. Ocean-exploration watches like Curry’s Deepsea, on the other hand, haven’t quite made it to the shores of celebrity. But hey—when you’re celebrating your NBA title at the White House, you can wear whatever you want.

Frances Tiafoe’s Tag Heuer Carrera

No one’s looked cooler at the Australian open than on-the-rise American Frances Tiafoe. His swirly technicolor set has been controversial, but it shouldn’t be—it rules. Tiafoe also recently wore a great watch to the premiere of Netflix’s new tennis doc series Break Point. This particular version of the Tag Heuer Carrera is skeletonized to let the wearer see inside the watch, much like Break Point is designed to let viewers see inside the tennis world. I’m sure this is exactly the parallel Tiafoe was trying to draw. 

Tyler James Williams’s Cartier Santos Dumont

Abbott Elementary’s Williams wore a whole safe deposit box’s worth of Cartier jewelry to the Critic’s Choice Awards: a nail-shaped tie pin, a gold necklace, the brand’s famous Panthère rings, the brand’s even-more-famous Love bracelet, and even a Love ring for good measure. But, of course, the pièce de résistance was Williams’s gold Santos Dumont. The combination of white dial and yellow gold watch is unbeatable.