Leonardo DiCaprio, Charlize Theron Among Hollywood's Hottest Watch Ambassadors

From left: Theron was sued by sponsor Raymond Weil after she was photographed wearing a Dior watch; Kruger is a brand ambassador for Jaeger-LeCoultre; Winslet wears Longines when she hits the red carpet; DiCaprio helped design a TAG Heuer watch that benefits the Natural Resources Defense Council.

Inside the arms race among luxury watchmakers to snag a Charlize (or a Leo or a Kate) to bandy their brands on the red carpet and beyond.

This story first appeared in the second annual Watches supplement to the Dec. 6 issue of The Hollywood Reporter magazine.

Austrian daredevil Felix Baumgartner wears luxury watchmaker Zenith's El Primero Stratos Flyback Striking 10th on his supersonic free fall from near space. Rolex burnishes its reputation for chic durability by lashing a custom Deepsea Challenge to James Cameron's submarine before it dives 10,898 meters to the bottom of the Mariana Trench. Jaeger-LeCoultre signs up Clive Owen and Diane Kruger; TAG Heuer snags Leonardo DiCaprio and Maria Sharapova. It's all part of an arms race among watchmakers to align brands with celebrities who possess enough -- and the right type of -- star power to enhance marques that are already perceived as exalted and expensive.

Watchmakers choose their faces carefully, striving to match a brand's ethos to those of celebrities and their fans. Some are called ambassadors, others spokespersons or "friends of the brand," and their deals and compensation vary widely -- from free watches and travel to promotional events and checks in the millions.

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Baumgartner was a good fit for Zenith -- whose most expensive watch, the men's Academy, fetches $90,000 -- because "Zenith has always associated its name with the spirit of adventure," says Katie Kinsella of Kinney + Kinsella, which handles marketing for luxury watch brands. Presumably that association includes adventurer Ryan Seacrest, who wears Zenith's Captain Winsor Chronograph on American Idol.

For TAG Heuer, DiCaprio and Sharapova lend cachet to a brand that's priced considerably lower than other luxury watches, and they participate in the design of their namesake models. DiCaprio helped design a custom link to benefit the Natural Resources Defense Council (though he wore a rose gold TAG Heuer Carrera 1887 to The Great Gatsby premiere in May). Similarly, Omega partnered with Daniel Craig on the Hour Vision Blue watch to benefit the blindness-prevention organization Orbis International, which the actor supports.

Longines calls its celebs "ambassadors of elegance" -- they include Kate Winslet, Bollywood actress Aishwarya Rai Bachchan and tennis greats (and real-life couple) Andre Agassi and Steffi Graf. In one of his first ambassadorship duties, Simon Baker introduced the Saint-Imier Collection in summer 2012 at the famed Prix de Diane Longines horse race in Chantilly, France.

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IWC integrates watches worn by its celebrity ambassadors -- including Kevin Spacey, Eric Dane and Matthew Fox -- directly into their screen work. Spacey's Frank Underwood can be seen wearing IWC timepieces on Netflix's House of Cards. This season, the brand's Big Pilot's Watch supplanted Panerai on the wrist of Josh Charles' alpha attorney Will Gardner on CBS' The Good Wife. IWC says it never pays for placements and that the watches are loaners, to be given back after shooting.

Watchmakers are cagey about the subject, but brand ambassadors typically are compensated with, at the very least, free watches. Owen chose Jaeger-LeCoultre's Duometre a Chronographe, and Kruger, given a Reverso by her mother when she was 18, wears the new Rendez-Vous (she also stars in the Jaeger-sponsored one-minute film Reinvent Yourself).

Watch brands don't break out the terms of their sponsorship deals, but aside from free merchandise, they usually involve compulsory travel to such big Swiss trade shows as Baselworld and SIHH, as well as corporate events. When cash is involved, it is as likely to go to a celebrity's charitable foundation or to a cause he or she supports as into their pockets.

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But the game of watch ambassadorship is not to be taken lightly -- case in point, Charlize Theron. According to documents released by The Smoking Gun, in 2005, the actress was paid $3 million to promote Raymond Weil's Shine watch collection. In 2008, she was slapped with a $20 million breach-of-contract lawsuit. Her crime: getting caught -- and photographed -- wearing a Dior watch at an event. (The suit was settled out of court.)

But watch ambassadorship usually is a lot less acrimonious. IWC approached Dane eight years ago after noticing he wore one of its watches on a photo shoot. He has been a brand ambassador ever since. "I was a watch fan to begin with, and I always loved what they were doing," says Dane. "I'm wearing the Top Gun Miramar right now." He notes the benefits of IWC ambassadorship extend beyond watches: "It may have started out as business, but for me now, it's less about the watches and more about the friendships I've made. I go to their parties, and let me tell you -- IWC, they throw great parties."