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John MayerLOS ANGELES - FEBRUARY 4: Guest Host John Mayer on THE LATE LATE SHOW with guests Andy Cohen, Alison Becker, & John Legend on Feb. 4, 2015 on the CBS Television Network. (Photo by Sonja Flemming/CBS via Getty Images) Image Credit: CBS via Getty Images

Seated in a 30th-floor suite at the Carlyle hotel, John Mayer was noodling through a few riffs on a glimmering new PRS Custom 22 guitar. It looked like a work of art as much as a musical instrument, its clear yellow finish revealing wood grain as brilliant as a tiger’s stripes.

But Mayer’s thoughts turned to a humbler possession that he treasured long ago: his first watch, a Star Wars-themed Armitron digital emblazoned with images of C-3PO and R2-D2.

“When you’re a kid, you don’t have much, so you are building these imaginary, macrocosmic worlds out of these really small things,” the platinum-selling singer, songwriter and guitar virtuoso said.

When he was growing up in Fairfield, Connecticut, Mayer, 37, slept with his head inside a cardboard box, in place of a pillow. That’s where he kept his prize possessions, most significantly his watch.

“I remember looking at it, and it was my friend,” he said. “It was one of the biggest things I ever owned in my life, if you were to amortize it in terms of where you were in your life and what it meant to me.”

The ensuing years have thrown more than a few distractions his way: seven Grammys, the string of tabloid romances (Jessica Simpson, Jennifer Aniston, Taylor Swift). But, if anything, watches have only grown in importance to him.

A prominent collector (he estimated that his collection, stored in bank vaults, is valued “in the tens of millions,” although he declined to cite a specific dollar amount), Mayer has established a reputation within the cultish watch community as a tastemaker, a discerning critic and a champion of horology.

Moonlighting from his career onstage, he contributes to the influential watch site Hodinkee and has been on the jury of the venerable Grand Prix d’Horlogerie de Geneve. In Hollywood, Mayer has become a go-to guy for other celebrities (Drake, Aziz Ansari) looking for advice on their watch purchases.

His platform as a pop star, in fact, gives him a unique opportunity: to translate the insular world of fine mechanical watch collecting to the iPhone generation. Here is a guy who has jammed with the Rolling Stones and dated Katy Perry after all, and who also knows how to accessorise a chief-executive-worthy pink gold Audemars Piguet with a tattoo sleeve.

“John is something of a watch-nerd icon,” said Benjamin Clymer, the 32-year-old founder of Hodinkee, which features watch news and reviews catering to next-generation aficionados. “I think, in a lot of ways, John made it OK to really go deep into watches and not be embarrassed about it. I can’t tell you how many guys have come up to me at events and said, ‘My wife or girlfriend thought I was crazy for caring about watches so much, until I told her John Mayer was the very same way.’”

It’s a ‘Syndrome’

Mayer’s own girlfriends have tended to view his watch obsession as a “syndrome,” the singer admitted.

Reclining on a white sofa in the Carlyle on a recent afternoon, Mayer, who was in New York for an appearance on Late Show With David Letterman, had that just-got-out-of-bed look. His rockabilly pompadour a bit mussed, he sat cross-legged, without shoes, wearing a black T-shirt and low-slung jeans by the Japanese streetwear brand Visvim.

“I think you’re born a watch person,” he said. “Even if you don’t own a watch for a while, you either get it or you don’t.”

He bought his first “real” watch, a Rolex Explorer II, not long after receiving his first “real” check from a record label, following the release of his 2001 breakthrough album, Room for Squares, which has sold more than 4.5 million copies.

“You take it home and you study and you wear it, and the first thing you notice is, ‘Whoa, this thing is heavy,’” Mayer said. “You’ve never felt weight shift like that on your wrist. It’s heavy in weight, but it’s also heavy in the sense that all these pieces are working together. It’s what I call the ‘density of design.’”

With its utilitarian white dial and steel bracelet, the Explorer II (current retail: $8,100 (Dh29,752)) is almost normcore by celebrity standards. Non-watch people may mistake it for Timex.

For Mayer, it was not the status he cared about. “You take it, and it becomes your thing,” he said. “You go: ‘You’re my one and only watch; you’re my Rolex. I got a Rolex.’ It’s like a Cadillac. Rolex transcends watches as a name. It’s ‘the Rolex of’ something, ‘the Cadillac of’ something.”

As he embarked on a life of endless touring, Mayer was learning that a watch can serve a psychological function, as a grounding mechanism, a home base.

“I remember thinking — and this is a very important feeling — that I could go anywhere with this watch, because I couldn’t be lost,” he said. “I could get lost in Paris, but I had my watch. Now, on its face, no pun intended, it doesn’t make sense. All your watch does is tell the time. But why do you feel strapped? Why do you feel equipped?

“It would take a lot of poetry to explain it.”

Poring through collector’s guides, Mayer discovered, was a way to decompress on the tour bus after a show. Soon he discovered the IWC Big Pilot’s Watch, a masterpiece of design minimalism.

“It’s a watch I identify with, that people identify with me,” he said. “Now, all it does is tell the time and the date, that’s it. But, man, how it does it.”

His code name on tour became “Big Pilot.” And he added the logo typically found on pilot’s watches (a triangle and two dots) to the 12th fret of his John Mayer signature acoustic guitar by C.F. Martin & Co. “It’s a little didactic, and cartoonishly so,” he said. “But this thing became my slide rule, my horizon line.”

By that point, he was ready to take the next step: vintage collector pieces.

The search

“I was a ‘new’ guy; I had to break the seal,” Mayer said. He did so by purchasing a coveted “double red” Rolex Sea-Dweller from the 1970s, which has the words “Sea-Dweller” and “Submariner 2000” printed in two lines of red type on its dial. “I take it home, and I do this thing — I think guys do it — you buy something and then you learn all about it,” he said. “It’s retroactive research.”

After a decade of serious collecting, Mayer was established enough as a connoisseur to ask Patek Philippe (the Geneva-based maker of ultra-high-end watches, founded in 1839) to make him unique pieces by request. One was a white gold 5004G with luminous hands, typically a feature associated with casual sport watches. He needed to see them on stage, he told the company.

“It was not about whether I wear each and every one on stage, but it has an intention to it,” Mayer said, comparing it to the watch Sir Edmund Hillary wore to the top of Mount Everest. “It’s made to support an endeavour.”

While he had become a connoisseur, he was no snob. As a man who hunts down vintage $130 Casio G-Shocks on eBay, he shrugs off what he calls the “L word” (luxury) and hopes that those outside the insular watch community will understand that his passion is educated and, thus, pure.

“I’ve always pitched this theory of, if a guy comes up to a restaurant in a red Ferrari, you kind of recoil,” he said. “But if you find out that the guy owned 14 of them, and he writes a blog on them, then you can appreciate it because you can trust that there’s a depth to it.”

The Apple Watch Conundrum

This raises the question about what he thinks of the Apple Watch, a potential head turner, but one that will have no sense of heritage in the world of horology.

“We’re all going to end up with the Apple Watch; I don’t care what you say,” Mayer said. “Even if you have to wear it on your right hand. Even if you wear it as a pocket watch, because I have a concept that you can slot the Apple Watch into a pocket, as a pocket watch. I think it’s a cool device, but there’s got to be another place to put it. I can’t give up precious wrist space for an Apple Watch.”

If, indeed, everyone is going to end up with the Apple, that may undercut a subtle joy of connoisseurship: the pleasure of belonging. “The watch community gets its power from being esoteric,” Mayer said. “We don’t want everybody to be involved in it.”

Mayer developed his love of old-school mechanical timepieces in an era of mobile phones, which all came with clocks. Journalists were routinely predicting that the wristwatch would soon join the rotary phone and manual typewriter in obsolescence. But a new generation of hipster refuseniks, Mayer among them, was learning to appreciate its analogue charms.

“There’s a mission creep on the word ‘hipster,’” he said. “It’s dismissive. It just means, ‘I want to emerge somehow; I want to differentiate myself.’

“Everybody is having a shared experience through all things,” Mayer continued. “We’ve all seen Breaking Bad; we’ve all seen The Jinx; we’ve all heard Serial; we all have an iPhone. Your trip through the iPhone is my trip through the iPhone. We all do the same things on it. It’s a rite of passage as you get older, you say, ‘I don’t want this universal experience all the time.’”

For a celebrity who had grown weary of a life lived on TMZ.com, the watch community offered escape. In that world, he was just “John,” a guy who loves watches.

“I would go to watch shows wearing my loupe and my badge, and I was there as a watch guy,” he said. “I loved relating to people only on the merit of being a collector.”

Surprisingly, Mayer said, few on watch forums such as Hodinkee seemed to resent the size or cost of his collection.

“I’ve encountered zero people being disheartened with the fact they don’t have something,” he said. “And they all say the same thing: ‘When I sell my script, when I make my record, when I get there, I’m going to get that.’”

“Here’s what is great about watch collecting,” Mayer said. “You don’t have to own a watch to be part of the conversation. In fact, most people who are commenting on the dial of the last iteration of the 5270” — the Patek Philippe Perpetual Calendar Chronograph coveted by collectors — “don’t own a 5270. But that’s like saying that most people who talk about the Chicago Bulls aren’t on the Chicago Bulls.”

Just Another 30-something blogger

When he writes about watches, Mayer assumes the role of passionate Everyman, in many cases coming off like any other scruffy, 30-something blogger.

In one Hodinkee post, he assembled a handy guide to the five best vintage Rolex watches under $8,000. In another, he chronicled his unlikely purchase of a women’s Chanel Mademoiselle Prive.

A widely circulated entry was his impassioned open letter to his beloved IWC, imploring it to pull back on the celebrity endorsements and trendy design flourishes. IWC fired a back a tart reply, in which it invoked a song by Mayer, I Don’t Trust Myself (With Loving You).

His goal as a watch pundit, he said, is not to show off, but to help others learn from his mistakes. The vintage Rolex market in particular “is a minefield,” he warned.

Last year, Mayer filed a lawsuit seeking $656,000 (plus damages and interest) from a Southern California watch dealer, over pieces that Mayer claims contain some non-authentic elements; at press time, the suit was pending.

It was a painful learning experience, if nothing else. “Nothing will teach you more than that feeling,” he said. “You want to learn to fight? Get hit in the face.”

But Mayer counts his uninspired purchases as part of the journey, comparing the act of building a watch collection to the creation of a personal gallery of tattoos on one’s own body.

“My first tattoo looks nothing like my last tattoo, and they’re the same thing,” Mayer said. He pulled up the right sleeve of his T-shirt to demonstrate.

“That’s the best koi fish you can find,” he said dismissively, nodding toward the crude fish tattoo he got at 18. “And that,” he said, pulling up his other sleeve to show off a lovely reinterpretation he got at 32, “is the koi fish that you want.”

He lowered the sleeve. “It all represents the trip through knowledge.”