CELEBRITIES WHO LOVE TO ROLL THE DICE, SPIN THE WHEEL, AND BET ON THEIR FAVORITE TEAMS
When it comes to gambling, celebrities are just like us. They put up their money and take their chances.
Betting provides something special in terms of having opinions or making decisions, or just feeling in your gut that you are lucky and having it work out. Even for the most famous, most recognizable people on the planet, the thrill is undeniable when things go their way, and the chips (digital or physical) pile up.
With that in mind, here is a celebration of the celebrities who take risks in front of the camera or behind the microphone or in the boxing ring – and still embrace the adrenaline rush that only a battle against the odds can provide.
QUEEN OF CARDS
Some people recognize Jennifer Tilly for her work as an actress in the Chucky series of horror movies. But, to those in the casino know, she is more famous as a presence at poker tables.
The longtime girlfriend of seasoned pro Phil Laak, she takes the game seriously and brings high glamour to high-stakes Texas hold ‘em. “There was a game where I brought my blinged-out Chucky doll,” Tilly told me last year. “I had him sitting on top of my chip stack with a $25,000 chip in his hand. Then I’d do a little thing where I would make like I was trying to pull it away, but he wouldn’t let me.”
How does Tilly, who has a little more than $1 million in live tournament winnings, celebrate a big money victory? “I remember winning the $5,000 buy-in Bellagio Cup [it paid her $124,455],” she said. “I went to Petrosian in the Bellagio, sat down, and ordered the caviar. Then I thought, I just won a big poker tournament. I’m a winning gambler… And I ordered a second container of caviar. I remember sitting there, eating the caviar and being, like, ‘Me fancy!’
One thing Tilly has learned from poker is how best to view money on the table. “If you’re going to play high-stakes poker, it doesn’t help to think of a pot as a Chanel purse that you want,” Tilly advised me. “Instead, you have to think of the chips as things that you get to play with. I think of them as Monopoly money. One good thing about keeping my money separate [for gambling and for living] is that my business manager doesn’t have to feel sad for me when I lose.”
KNOCKOUT GAMBLER
When it comes to gambling, the famously flashy boxer Floyd “Money” Mayweather is a man for all seasons. His sports betting is frequent and famous – in September, he snagged $40,000 by betting on his hometown WNBA team, the Las Vegas Aces and, for him, that’s a modest cash – but he does not mind winning on the casino floor as well.
Over the years, Mayweather has logged wins and losses all over the place. There was the time he hit a video poker jackpot on a 10-hand game, taking down a little more than $100,000. According to Business Insider, the undefeated fighter (with a record of 50 wins and 0 losses) won, on one occasion, $500,000 playing blackjack. As for poker, he’s claimed to enjoy the game for high stakes while on his private jet.
And if he gets bored, he can always play his signature slot machine. Last year, the Money Mayweather machine debuted. No newcomer to laying down challenges, he greeted its premier by posting, “You’ve seen me own the ring. Now it’s your turn to play the Money Mayweather slot game.”
That’s one Mayweather challenge that even the least pugilistic among us can take on.
CELEBS FIND THE DICE TO BE NICE
Craps is one of the most action-packed games that you’ll find in a casino. On a good night, the energy around a craps table is so hot that it almost feels as if the table will levitate. It’s no wonder, then, that craps is beloved by the people who keep us entertained. The game is such a rush that it crosses over to be something beyond gambling and, when the dice fall correctly, more of an all-out celebration.
Time-tripping back to the golden age of Las Vegas, Frank Sinatra clearly understood the allure of tumbling dice. He got the total VIP treatment at the Sands and had what is said to have been an unlimited credit line. A 1960 photo shows the Chairman standing alongside a Sands craps table, cig in hand, maybe contemplating an impending wager. Sixty-five years later, Sin City pays tribute to the enduring entertainer and avid gambler with a street called Frank Sinatra Drive. No doubt, that is a win for the top-notch crooner.
Bold-face names of the modern age who are said to enjoy craps include the likes of ex-NBA star Charles Barkley and members of the rap group Migos (a video on Instagram shows Offset shooting the dice and, in classic craps lover fashion, calling out for his number).
The late comedian Norm Macdonald had a soft spot for the rolling bones. I happened to be with him, after his standup gig at the House of Blues, when he played a long session of craps. Ever the contrarian, Norm liked to play the “don’t” – that is, betting on the house to win and his fellow players to lose. He cheekily called it his “pensioner’s system” and enjoyed splashing around chips on a wide range of bets.
Echoing a sentiment that we can all relate to, he told me., “If I’m in a casino, I’m gonna gamble.”
And he did!
DRAKE TAKES GAMBLING FOR A SPIN
Though the Canadian rapper Drake might be most famous for his sports betting – he’s gone out of his way to post high-stakes betting slips to social media; for the 2024 Super Bowl, he wagered $1.1 million on the Kansas City Chiefs beating the San Francisco 49ers ; the Chiefs won in overtime and so did the rapper nicknamed Champagne Papi – he is far from a stranger to the same casino games that we all enjoy..
But, clearly, when it comes to laying down chips on the felt, Drake has his own way of doing things.
Footage on YouTube shows him winning and losing money at stakes that few of us can imagine mustering. His game of choice? Often, it is roulette. And he is not shy about showing off the casino game he prefers: He is said to have a six-figure watch with a spinning roulette wheel built into the design.
Where real roulette wheels are concerned, six figures are also the order of the day.
On at least one occasion, Drake had some $250,000 worth of wagers on a single spin of the roulette wheel during a session at Aria in Las Vegas. He had a series of so-called “complete bets,” which left him with 27 wagers, covering the inside of the roulette-felt’s layout. He was playing on a single-zero wheel, which provides better odds than the double-zero iteration. Drake posted a photo of the bet happening – but he did not reveal the outcome. That said, if his lucky number 11 hit, with $20,000 on the spot, he’d net nearly half a million dollars.
Other times, outside of the brick-and-mortar casino, we’ve seen him playing online roulette for big money – “My bets are ridiculous,” he’s heard admitting in one video – and when it comes to gambling, he likes to share the love. Playing online, he showed fellow rapper Lil’ Yachtie just how it’s done. We should all be lucky enough to have Champagne Papi as a roulette coach.
Michael Kaplan is a journalist based in Brooklyn, NY. He is the author of five books. The most recent one is Advantage Players: Inside the Winning World of Casino Virtuosos, Master Strategists, and Mathematical Wizards. Kaplan has written for publications that include the New York Times Magazine, Wired, and GQ. He is a senior features writer with the New York Post, writes the gambling column for Cigar Aficionado, and wrote an article on baccarat queen Cheung Yin “Kelly” Sun that is being developed into a feature film with the actress Awkwafina attached to star as Kelly.
