What Regina King, Tim Story Have in Their Hallowed Watch Collections

Regina King

Regina King does not commemorate location shoots with typical souvenirs like novelty T-shirts or postcards. The actress — who won her first Emmy this year for her work on the ABC drama American Crime — prefers more lasting remembrances. "I’ll go to a dealer who specializes in watches that are hard to find. It gives the watch a story," says King, 44. "Watches are pieces of art that you get to wear."

King got her first serious watch, a vintage Rolex, in 1999, when she was filming the Lifetime telefilm Where the Truth Lies with Marlee Matlin in Portland, Ore. "There’s no sales tax up there, so I thought this was the opportunity to take the leap," she says. "I couldn’t have been older than 28."

The actress, who got her first big break at age 14 when she starred on the classic NBC sitcom 227, leans toward statement-making pieces — like her sizable 43mm-diameter Maurice Lacroix with a diamond bezel. Larger-size watches aren’t always suitable for the red carpet, but there are exceptions.

"I have a Maurice Lacroix that’s not too chunky, and it has a few diamonds, so it goes really well with a tennis bracelet," she says. As for her dream watch, it’s diamond-free. King covets a 1969 Patek Philippe, one of the Swiss watchmaker’s collaborations with Tiffany & Co. The piece is "perfect," she says, but it’s on her wish list for now. Price tag at a recent auction? About $200,000.

The actress is due for a new addition, albeit one that won’t cost her six figures. King spent the better part of the past year working in Austin on American Crime and on HBO’s The Leftovers. "I didn’t get one my first year working in Austin," says King. "This is a good reminder to get on that."

Robert Herjavec

Shark Tank star Robert Herjavec, Rolex devotee, often will purchase a watch to mark a special occasion. "A watch is still one of those things that makes you feel special and important," he says. "It’s a bit of a celebration."

When he was starting out in business, Herjavec admired his boss’ yellow gold Rolex Day-Date President. At dinner one night, he inquired about it and was told it cost $25,000. "The idea that someone could afford a watch worth that kind of money just blew my mind. I said, 'If I ever make it, that’s the watch I will buy.' " And when he sold a software business in 2000 for $30 million, he did. Herjavec now owns about 10 Rolexes and a few other pieces including a few Blancpains. His everyday watch is a Rolex Daytona in white gold with a blue dial.

"It’s very durable and beautiful, and ?it looks great with a pair of jeans or a suit," says the car enthusiast, who races Ferraris. While Herjavec (who competed this year on Dancing With the Stars) made his fortune in the tech world, he’s not drawn to electronic watches. "I am a very high-tech guy — I’ve got all the latest tools and apps — but there is something about the mechanism of a mechanical watch that feels very old school and durable to me."

Kevin O'Leary

"It’s your relationship with a watch that makes it unique, that makes it an old friend," says investor and Shark Tank co-host Kevin O’Leary. Known as the show’s toughest shark, O’Leary owns 32 pieces.

Years ago, when thousands of inquiries came in after he wore his Jaeger-LeCoultre Reverso on TV, he realized the impact watches can have. The piece had a red leather band, which has since become a style signature of his. O’Leary’s love of watches goes back to boyhood, when his Swiss stepfather would take him to watch museums and dealers in Geneva.

But even this master wheeler and dealer has one thing that’s out of his grasp, at least for now: a vintage two-tone Cartier Panthere that was stolen from him. He was wearing it when he famously signed a $4.2 billion deal to sell The Learning Co. to Mattel in 1999. "I need to get that watch back. Someone has it somewhere."

Tim Story

At the start of every new project, Tim Story treats himself to a watch. His tradition began on the set of Fox’s Fantastic Four (the 2005 version, not the failed 2015 reboot) with an $8,500 splurge on a Panerai Luminor 1950.

For his 2016 movie Ride Along 2 — a follow-up to the 2014 Ice Cube-Kevin Hart comedy — Story, 45, acquired an IWC Pilot’s Watch Chronograph Top Gun Miramar, based on the one Tom Cruise wore in the hit 1986 film. "But I didn’t get it because of that," says Story with a laugh. "I got it for the look."

In the past few years, the Los Angeles-born Story — who graduated from USC film school in 1991 — has become one of Hollywood’s most consistent hitmakers. He not only has succeeded in two very different genres — superhero movies (Fantastic Four and Fantastic Four: Rise of the Silver Surfer) and urban comedies (Think Like? a Man and Ride Along, both of which spawned sequels) — but also has made history along the way. Story is the first African-American director to take the reins of a Marvel franchise and the first whose films have surpassed $1 billion in total box office.

Stylish — though unfussily so — Story says he always has found "a confidence to having a nice watch. Now I feel naked not wearing one. If I walk out in sweats and a T-shirt but have a nice timepiece on, I feel like a man." He says he plans on passing down his watch collection to his 4-year-old son, Mason, the youngest of his three children with his wife of 12 years, Vicky. But not until he’s older. "Maybe when he’s in his 30s or 40s and truly realizes the value of them, I’ll say, 'Here you go,' and he’ll take care of them. That’s cool to think about."

Gregg Sulkin

British actor Gregg Sulkin fondly remembers when he was 17 and his father gifted him with a classic Cartier Santos 100. "I just remember putting it on my wrist and feeling like I was entering adulthood," says Sulkin, now 23 and best known for his work on such teen-friendly projects as MTV’s Faking It and a string of Disney projects including Wizards of Waverly Place. "Plus, my dad was a big inspiration to me growing up, and I always wanted to be like him in every which way possible." At the time, says Sulkin, his dad had been robbed on a street in London for his watch. "He told me to wear mine with pride but also be careful."

For Sulkin — whose Instagram account counts 2.1 million followers — that means keeping his Cartier locked up in a safe, one he hopes to fill up over the next decade. He kick-started the collection with a Rolex Milgauss. "It’s my favorite watch," adds Sulkin, whose girlfriend is actress Bella Thorne. "I worked very hard for that watch. Hopefully it?will increase in value — not that I ever want to sell it — because it is a collector’s piece. I eventually want to pass them down to my children."

Sulkin likens the Milgauss to a Range Rover Sport, appropriate for any occasion. "You could wear it for?a coffee, and it looks cool, or you can dress it up with a suit, and suddenly it looks polished. That’s like my personality. Like, I’m very chill with sweatpants and a T-shirt when I’m hanging out, and then I can also be at a big fancy industry event where I kind of have to look appropriate."

Next up: The dashing actor has his eye on a Rolex Daytona that his older brother and father share, and he hopes they invite him into their watch-swapping club. He also would love a Patek Philippe Nautilus and an Audemars Piguet Royal Oak. The purchases are easy for Sulkin to justify: "Cars depreciate in value. If you can buy something you love, and it keeps its value or increases, as watches often do, it’s a no-brainer. I don’t have to think about buying a new watch."