Celebs Who Love a Gamble/Bet
May 16 2025, Published 3:19 a.m. ET
Celebrities are often posting pictures of themselves on private jets enjoying seemingly blissful, and expensive, holidays. It’s also not unknown for them to have other interests outside their profession, with many starting their own clothing, make-up, perfume, and alcohol brands.
However, one such past time that is also hugely popular amongst many celebs is gambling. Whether it’s playing a game of blackjack or poker, or placing a wager on a big sports match, gambling is a popular past time for the rich and famous.
Floyd Mayweather
Floyd 'Money' Mayweather won an astonishing 15 major world championships over five weight classes, from super featherweight to light middleweight. Retiring undefeated, he is estimated to have earnt $1.1billion during his glittering boxing career.
Since retirement, Mayweather has continued to rack up several big money wins thanks to his fondness for sports betting. Something he is not afraid to share details of with his millions of fans on social media.
In 2015, he famously went on a four-day betting streak, placing $350,00 on the NBA and Gennady Golovkin's fight with Willy Monroe Jr. The “Money” went home with a handsome $827,272 for his troubles.
That win however, pales into insignificance when compared to one of his biggest wins. In 2014, Mayweather spent a month betting on the NFL and began by banking $1,825,714.28 after betting on both the Seattle Seahawks and Indianapolis Colts to win by more than 7.5 points.
A further $815,000 on the Denver Broncos to beat the New York Jets by more than 7.5 points, saw him win another $1.4million. The Arizona Cardinals defeat of the Oakland Raiders saw another $800,000 stake turn into $1.5million. In total, the former champ picked up around $4.7million dollars in just one month.
Matt Damon
Matt Damon reportedly discovered a love of poker while researching his role in the 1998 film “Rounders”. The story follows two friends who need to win a high-stakes poker match in order to quickly pay off a debt. A “rounder” refers to a person traveling from city to city looking for high-stakes card games.
As part of his preparation, Damon, along with fellow actor Ed Norton, got seats in the World Series of Poker and also played on the New York underground poker scene. Like his good friend Ben Affleck, Damon enjoys playing socially, and even took part in the 2009 World Series of Poker as part of the $5,000 buy-in Ante Up for Africa Charity Event.
Like Rounders, there are many films that now incorporate gambling scenes and topics as attitudes and laws around the US become more relaxed. Nowadays, many US punters can head online to an online casino, redeem a casino bonus and play their favourite casino games like Matt Damon if they are in an eligible state.
Ben Affleck
The actor, writer, and director, Ben Affleck, is famed for his movie skills, but he’s also a well-known poker and blackjack player too. His achievements include winning the California State Poker Championship in 2004. A victory that saw him claim a seat at the World Poker Tour final table.
In 2001, the actor was reported to have won $800,000 in a single night of blackjack, and his skills are claimed to be good enough to hold his own amongst the top-level professional players.
Famously, Affleck was allegedly banned from the Hard Rock Casino in Las Vegas after being caught counting cards. While the practice is not illegal, casinos often ban individuals for this practice as it tips the odds in the player’s favour.
Jennifer Tilly
The renowned Oscar-nominated actress is famous for her roles in films such as “Bound”, and the “Chucky” franchise. But she is also a highly respected professional poker player, having achieved significant success over the years.
In 2005, she won the World Series of Poker Ladies Event and the World Poker Tour Ladies Invitational Tournament. With an estimated $1 million in earnings, Tilly was inducted into the Women in Poker Hall of Fame in 2022.
Tobey Maguire
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Another actor with a fondness for the card table, is former Spiderman star Tobey Maguire. He was allegedly involved in illicit underground high-stakes poker games with other celebrities and high rollers that were revealed in the memoir “Molly's Game”.
The book was later turned into a successful 2017 movie, and follows Bloom as she becomes the target of an FBI investigation after the underground poker empire she runs for Hollywood celebrities, athletes, and business tycoons, is exposed.
Maguire reportedly won substantial sums of money during his days of playing underground card games, with some reports suggesting he scooped as much as $36 million.
Many celebrities have been known to enjoy the thrill and glamour of gambling, including boxer Floyd Mayweather and actor Tobey Maguire. Whether it be as a hobby or as part of research for an acting role like Matt Damon and his role in “Rounders”, casino games are a hit amongst celebrities. It seems that the gambling lifestyle allows celebrities to combine both risk-taking with luxury high-end casinos in iconic locations around the world such as Las Vegas.
