Seriously, the relationship many of us have with our beloved timepieces could be considered quasi-transcendental, such is the love we have for them. That remains true for some men even when they become world-famous and leaders in their fields.

Much has been made about famous actors and sportsmen who wore certain watches, even beyond the usual commercial endorsements that some of them enjoy with their celebrity status. But they are not the only men who have loved the prized possessions on their wrists (or in their pockets, as you will soon read). There have also been presidents and prime ministers who have enjoyed owning and admiring watches, not to mention trend-setters and creatively daring men who changed the way we view arts and culture.

In this article, we will seek some understanding of the unique relationship and affinity that certain famous men had for their watches. It’s a relationship that’s telling about the man, his outlook on life, and even the times in which he lived.

John F. Kennedy

JFK’s obsession with watches is well-known. Kennedy was one of those lucky men who had literally every watch he ever owned given to him by someone else. That didn’t diminish his love for watches, though. For example, athis inauguration on January 20th, 1961, Kennedy was wearing an Omega Ultra Thin (Reference OT3980), which had been given to him by Grant Stockdale, a senator from Florida. Inscribed on the watch’s caseback was the inscription “President of the United States John F. Kennedy from his friend Grant.” It’s said that JFK wore the watch for good luck on that day, given that Grant gave it to him months earlier, well before Kennedy beat Richard Nixon in the general election by a mere few thousand votes.  

Image credit: Robert Knudsen. White House Photographs, Omega Museum.

A favored watch was a water-resistant, 14­karat yellow gold cased Nastrix automatic watch that had been given to JFK by the Washington socialite couple and major Kennedy donors, David and Evangeline Bruce. According to the President’s secretary, Evelyn Lincoln, JFK would often wear the watch during his morning swims in the White House pool. Another favored watch was a Hamilton offered to him by then Governor David Lawrence of Pennsylvania in 1962, which had photo-engraved pictures of Kennedy’s two children, Caroline and John, engraved on the dial.

JFK's watch from Marilyn Monroe, which sold for $120,000 at auction in 2005.

Perhaps his most infamous watch was that given to him by Hollywood legend,Marilyn Monroe. It’s reported that the president was shocked with the gold Rolex (accompanied by a love poem from Monroe) on which was inscribed, “JACK - With love as always from MARILYN - MAY 29th 1962,” because he didn’t want his wife, Jackie, to find out about his torrid affair with the movie star. He never wore the watch, instructing an aide to get rid of it. And then there was the most tragic of JFK’s many watches: the 18-carat gold Cartier given to him by Jackie on their wedding anniversary in 1957 that was on his wrist when he wasbrutally assassinated in broad daylight in Dallas on November 22nd, 1963.

Winston Churchill

Anyone who knew the famous British wartime Prime Minister knew about one of his most prized possessions - the one he dubbed ‘the Turnip.’ The ‘vegetable’ in question was in fact a quite beautifulBreguet pocket watch, which was attached to a heavy gold waistcoat chain. Churchill was given the watch by his father sometime in the 1890s when Winston was still a young man. He always wore it around his waist and many recount how he almost never went without it.

The pocket watch remains in perfect working order and is today owned by Churchill’s great-grandson, Randolph. The famous watch has beendescribed in great detail, some of which is worth noting here: at the end of its chain is a small round gold case which contained some of the following: a V for Victory emblem; a silver head of Napoleon Bonaparte, who Winston admired greatly; a garnet stone set in a gold heart, which was a gift from his wife Clementine on their wedding day in September 1908; and another gift from Clementine, a golden heart given to him on his 90th birthday, less than eight weeks before his death.

There are manydelightful stories about Churchill and his treasured ‘Turnip.’ One story was how he ‘tested’ his scientific advisor, Professor Lindemann, one day after lunch. It’s said that Winston placed his pocket watch on the table and stated in his incomparable, booming voice, “Prof, tell us in words of one syllable and in no longer than five minutes what is quantum theory.” Lindemann rose to the challenge and did so without hesitation, resulting in rapturous applause and mirth from Churchill and those gathered! Another story is told by Edmund Murray, who was Churchill’s bodyguard, about the time he told Winston that it was one o’clock and thus time for lunch. Churchill whipped out his Breguet pocket watch and consulted it, and then declared, “No, it’s only five to one. Why do you wish to rob me of five minutes of my life?”

Churchill's 'Turnip'

Churchill was not the only man who loved his pocket watch long after they had gone out of fashion. Another famous man who was said to have loved pocket watches was 1950s Hollywood legend, James Dean. We will look at two other Hollywood actors and their love affair with their watches.

Paul Newman

Few actors were more famous for as long as Paul Newman was. And it was Newman that single-handedly turned a respected but not that popular watch model into one of the most famous watches ever. In fact, it was that iconic watch that set a then record for the most expensive watch ever sold. The watch was Newman’s own 1968 Rolex 6239 Cosmograph Daytona with white panda dial, which soldat auction at Phillips' New York for a final price of $17,752,500 in October 2017. For many, Newman’s Rolex was considered the ‘Holy Grail’ of famous vintage watches. The watch seemed to somehow transcend ‘mere’ watch collecting, such was its pull on those with real bucks to spend on super-expensive watches.

Image credit: Everett Collection

But for Newman it was never ‘just’ a watch or something that he wore a few times for publicity sake or the like. No, it was a watch that he wore almost continuously from the day his wife, the actressJoanne Woodward, gave it to him as a gift until the day he gifted it to his daughter’s boyfriend, James Cox. Paul Newman was photographed many times wearing his Rolex, including at the 1973 Cannes Film Festival alongside his wife and in numerous photo ops the actor did. The sporty watch with its Art Deco-inspired dial had been inscribed on its caseback with his wife’s words: “Drive Slowly Me." Woodward’s words to her husband were poignant in that Newman had become a huge motorsport enthusiast by the time she gave the watch to him in 1972. His love of fast cars and motor racing was equal to that of another Hollywood legend who also loved watches,Steve McQueen.

Robert Downey, Jr.

Yes, Iron Man has a real thing for watches. The critically acclaimed actor, Robert Downey Jr, became Hollywood’s highest-paid actor at the time thanks to his role in blockbuster action hero movies. We certainly learned about his love for watches during his interview withGQ Style for their debut issue in May 2016. GQ even filmed a Youtube video in which the actor prattles on about his watch collection, which can be seenhere and which had over 10.5-million views on Youtube as of June 2020.

The GQ video highlights nine of the watches in his collection, and which includes a magnificent Jaeger-LeCoultre AMVOX3 Tourbillon GMT that’s worth a cool $125,000. According toDowney, “I wore it in Iron Man 2, it’s probably my best watch.” No kidding . He probably has others stashed away. Onewatch reviewer wrote a rather freaked-out entire article about when Robert Downey Jr. left his prints in cement at one of those famous imprint ceremonies that stars do at the TCL Chinese (formerly Grauman’s Chinese) Theater in Hollywood. The reason for the freak out? Turns out that Iron Man was wearing a Greubel Forsey Double Tourbillon 30° Technique watch, valued at no less than $560,000. How close he came to accidentally letting that watch fall into wet concrete as he leaned over to leave his handprints! We think that writer had a good point.

Gianni Agnelli

Gianni Agnelli, the former Chairman and at one time principal shareholder of Italian car company FIAT, was a billionaire industrialist. Agnelli was Italy’s richest man for many years, at one time overseeing what amounted to 4.4% of the country’s entire GDP. He was the owner of legendary Italian soccer club, the Torino-based Juventus, and a member of the Italian Senate for life. He also had numerous affairs with women, which is why he was known as the ‘Rake of the Riviera,’ and was a consummate bon vivant who knew how to live the high life. He wasthe iconicEuropean playboy and jetsetter of the 1960s and 70s.

Gianni Agnell's signature way of wearing a watch

Agnelli was also known for his beautifully tailored suits and impeccable good taste in clothing and accessories. Hissartorial sense was legendary. But his taste could be eclectic and even idiosyncratic. For example, he was known to wear hiking boots or moccasins with his bespoke suits because, well, it was comfortable and he liked it that way! But probably his most iconic contribution to fashion had to do with watches - or, rather, how he wore them. It was Gianni Agnelli that introduced the world to a simple concept: wearing a watch not on the wrist but over the cuff of his shirt.

Why he wore his watches in that way is not entirely known, although there are opinions about that. His friend, the Greek writer and journalist Taki Theodoracopulos, had atheory that Agnelli wore his watches over his cuff because Italian tailors of the day cut shirt cuffs very close to the wrist and so Agnelli wore his watches, of which he had many and which he loved to collect, over the cuff instead. It has also beensuggested that Agnelli did that in order to simply save time when looking at his watch or even to save the watch from rubbing against his handmade shirts and fraying them. Whatever his reasons, Agnelli starteda trend: Italian fashion designer Valentino stated he did the same with his watches, as did artist Andy Warhol’s business manager Fred Hughes. Speaking of Andy…

Andy Warhol

Andy Warhol, the King of Pop Art and one ofthe iconoclast trend-setters of the 20th century, was an avid collector of watches, especially eye-catching ones. Histaste for watches was somewhat similar to his own aesthetic as both an artist and man, as well as his famous New York City studio. The Factory: industrial yet refined, and somewhat minimalist, but always eclectic and even crazy.

A favorite of his was a rare4021 Rolex from the 1940s in an 18-carat rose gold case. It was a beautiful watch with its silver dial and blue hands with Arabic hour markers. Probably the watch most closely associated with Warhol was Cartier’s Tank Louis. He is known to have loved the watch’s simple yet dramatic lines and did much to popularize that Cartier model among New York’s glitterati and the international fashion-forward set. Warhol had this to say about his Cartier Tank: “I don’t wear a Tank watch to tell the time. In fact, I never wind it. I wear a Tank because it’s the watch to wear.”

Unlike many watch collectors, Warhol was not interested in watch brands or even the history behind legacy names in the watch industry. Like a true artist, for him it was all about the design, the aesthetic. He loved certain watches for how they looked to him and what they evoked, not what they were or who made them. That is why Warhol’s watch collection came to be known as one of the most eclectic ever. And quite a collection it was. No less than 100 watches were found in his home after his sudden death in 1987.

It is believed that Andy Warhol supposedly kept his large watch collection in a large box hidden at the bottom of his closet. It was said that he often loved to open the box simply to look at their colors and feel them. For Andy Warhol, watches were all about the visual and the tactile. He certainly wouldn’t be alone in that among watch collectors.

As with all of us who love and admire watches, there have been many famous men who have known the immense pleasure that owning timepieces can bring to one’s life. How lucky for them - and us.