There are professional gamblers who become celebrities in their own right — players like poker whiz Nick “the Greek” Dandolos; Thomas “Amarillo Slim” Preston Jr., who was both a poker ace and a racetrack aficionado; and pool hustler Ronnie “Minnesota Fats” Wanderone (who borrowed his nickname from the fictional character played by Jackie Gleason in “The Hustler.”)
But then there are celebrities in other fields, like entertainment and sports, who love to gamble, and sometimes do very well at it. Looking back into Hollywood history, for instance, Lucille Ball of “I Love Lucy” fame gambled on backgammon, her favorite game. Suave leading man Cary Grant played games of chance on the SS Rex, a gambling boat anchored in international waters off the coast of Santa Monica. Omar Sharif, star of “Lawrence of Arabia” and “Dr. Zhivago,” was a take-no-prisoners contract bridge player and horse racing fan, and was said to have once lost more than a million dollars in a single night.
To assemble a list of modern-day celebrity gamblers, concentrating on those who have been particularly successful at the pursuit, 24/7 Tempo reviewed a study published by CasinoBankingMethods.com, a guide to online casino banking options. The site’s researchers used a variety of sources, including search results, news reports, and publicly disclosed information, to identify celebrities who enjoy gambling, then focused on those who had won significant amounts of money. They then determined their major winnings, their preferred gambling games, and the extent to which their winnings contributed to their net worth. (However much they may have earned, through gambling or any other means, these are 20 celebrities who died broke.)
CasinoBankingMethods.com offered specifics about some of these famous people’s successes. Paris Hilton, for instance, can claim blackjack victories of $30,000 and more than $50,000. Ultimate Fighting Championship CEO Dana White has proven adept at blackjack, too, playing for $25,000 a hand. Cameron Diaz plays blackjack, too, but made $2 million out of slot machines. As for Drake, he once took home $17 million from a single spin of the roulette wheel.
Scroll down to see 10 celebrities who’ve won big at gambling:
10. Paris Hilton
- Type of gambling: Blackjack
- Winnings: $80,000
- Net worth: $300 million
9. Ashton Kutcher
- Type of gambling: Sports betting (college footfall)
- Winnings: $750,000
- Net worth: $200 million
8. Ben Affleck
Ben Affleck attends the Los Angeles premiere of Amazon Studios The Tender Bar on December 12, 2021 in Hollywood, California.
- Type of gambling: Blackjack
- Winnings: $940,000
- Net worth: $150 million
7. 50 Cent
- Type of gambling: Blackjack
- Winnings: $1 million
- Net worth: $40 million
6. Dana White
- Type of gambling: Blackjack
- Winnings: $2 million
- Net worth: $500 million
5. Floyd Mayweather
- Type of gambling: Blackjack
- Winnings: $5.9 million
- Net worth: $400 million
4. Cameron Diaz
- Type of gambling: Slot machines
- Winnings: $25 million
- Net worth: $140 million
3. Leonardo DiCaprio
LOS ANGELES, CALIFORNIA - JANUARY 19: Leonardo DiCaprio speaks onstage during the 26th Annual Screen Actors Guild Awards at The Shrine Auditorium on January 19, 2020 in Los Angeles, California. 721359 (Photo by Kevork Djansezian/Getty Images for Turner)
- Type of gambling: Poker, slot machines
- Winnings: $33 million
- Net worth: $300 million
2. Tobey Maguire
- Type of gambling: Poker
- Winnings: $40 million
- Net worth: $75 million
1. Drake
LONG BEACH, CALIFORNIA - OCTOBER 30: Drake speaks onstage during Drakes Till Death Do Us Part rap battle on October 30, 2021 in Long Beach, California. (Photo by Amy Sussman/Getty Images)
- Type of gambling: Roulette
- Winnings: $70 million
- Net worth: $250 million