Gambling has long been a popular pastime among celebrities, but the stories making headlines over the past year have taken things to a whole new level.
From courtroom controversies to live-streamed gambling sessions involving millions of dollars, stars have found themselves at the center of some of the biggest betting headlines in recent memory.
The connection between celebrity culture and gambling has become even more visible in recent years, from rappers streaming multi-million-dollar betting sessions on Twitch to high-profile athletes facing gambling-related investigations.
Some stars have made gambling part of their public image, while others have partnered with betting companies, and a few have found themselves embroiled in controversy.
We’re taking a look at the stars most closely associated with gambling today, as well as how casinos and betting have shaped music, movies, and pop culture over the years.
Drake’s bets are getting attention
Drake reportedly signed an endorsement deal with Stake worth an estimated $100 million in 2022, and his gambling activity has made headlines ever since. The rapper allegedly lost up to $35 million over the course of a year while using the platform, and referred to 2025 as his “roughest gambling year” yet.
Drake has also faced legal scrutiny over the partnership. A Missouri man filed a class action lawsuit against Drake and streamer Adin Ross, alleging they misled fans by promoting what the lawsuit describes as an illegal online casino. Later in 2025, another class action lawsuit alleged Drake and his associates used money from gambling companies to artificially inflate his streaming numbers. Drake has denied wrongdoing, and the allegations have not been proven in court.
Stars are inking endorsement deals
It’s not just about playing the games. Plenty of celebrities have turned gambling into a business opportunity. Nick Cannon has shared his betting habits online, while Drake and Floyd Mayweather have signed endorsement deals with betting platforms.
Brands continue to invest heavily in celebrity partnerships as the industry grows. According to the American Gaming Association, U.S. sports betting revenue rose about 25% from 2023 to 2024, reaching a record $13.71 billion.
The games themselves haven’t changed, and superstars like Ben Affleck have made headlines for their love of blackjack.
What has changed is where people play, and sites like SportsLine keep a running list of vetted places to find games to play online, all from licensed casino operators. The same celebrity culture that helped make casino nights glamorous has also drawn more attention to regulated online gaming options.
The NBA’s gambling scandal pulled in more than just players
Basketball fans got a shock in 2025 when a sweeping federal investigation tied current and former NBA figures to illegal sports betting and rigged poker games. Miami Heat guard Terry Rozier was among those arrested and charged in a sports-betting case, alleging he provided nonpublic information to help bettors profit from NBA prop bets, while Portland Trail Blazers head coach Chauncey Billups was arrested in a separate but related case involving an alleged Mafia-backed rigged poker ring.
By early 2026, the fallout continued. The Miami Heat waived Rozier in April after he missed the entire 2025–26 season while facing federal charges, and former NBA player Damon Jones became the first defendant in the investigation to plead guilty after initially denying the allegations. The case remains ongoing, with multiple defendants still awaiting trial or sentencing.
Old Hollywood habits still hold up
Not every celebrity gambling story is a scandal. Sometimes it’s just classic Las Vegas. Ben Affleck has long been known as one of Hollywood’s best blackjack players and famously made headlines in 2014 after a Las Vegas casino stopped him from playing blackjack over allegations he was counting cards.
The late Robin Williams was among the celebrities who participated in high-profile poker events, while Paris Hilton has frequently shared photos and videos from casino trips with fans on social media. Michael Jordan‘s legendary gambling – whether on golf, cards or just about anything else – has been part of his public image since his playing days, becoming one of sports’ most enduring stories.
Movies and music never stopped loving a casino story
Even celebrities who aren’t personally known for gambling have helped shape the way audiences view casino culture through their work. Hollywood has created an entire genre around high-stakes games and big-money drama, from the heists of Ocean’s Eleven to Casino Royale, and The Card Counter. There’s also Molly’s Game, based on the true story of Molly Bloom, who ran exclusive underground poker games attended by celebrities and other high-profile players.
Music has embraced gambling imagery as well. Lady Gaga’s “Poker Face” turned casino terminology into a pop anthem, while rappers have frequently used high-stakes betting as a metaphor for risk, wealth and excess.
It’s no surprise that celebrity gambling stories continue to attract so much attention. Casinos and betting have been part of movies, music and pop culture for decades, making the real-life headlines feel instantly familiar.
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