10 Musicians Who Are (or Were) Passionate About Gambling

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Gambling draws people from all walks of life, including musicians. The thrill of taking a risk and the exciting atmosphere of the casino still appeal to people, or perhaps are even more appealing, after they have amassed fortunes. For these ten musicians, gambling in many different forms has remained a passion.

1. Madonna

Madonna, the singer known as the Queen of Pop, has established a substantial net worth — which has been estimated to be over a billion dollars at some points in her career. She has surprised people by continuing to play the lottery well after making it big and earning a fortune. In 2012, she won $250,000 after buying 100 lottery tickets. Since she didn’t need the money, she donated it all to a Malawi project for building schools.

2. Lady Gaga

Known for her over-the-top looks and powerful vocals, Lady Gaga has established a huge fan base for her music and even broken into the acting world. It turns out that this musician and actor is also a gambler. Perhaps this interest helped her write one of her most popular hits, “Poker Face,” which quickly became a chart-topping hit after being released in 2008. While online options like Lukki casino exist, Gaga prefers to visit land-based casinos.

3. Gladys Knight

Gladys Knight, also known as the Empress of Soul, has won three Grammy Awards throughout her singing career and has been nominated for ten more. While she was a rising star in the world of music, she was also struggling with a gambling addiction. Before quitting gambling, she experienced huge wins and losses playing baccarat. Knight credits the support of Gamblers Anonymous for helping her walk away from the casino tables.

4. Drake

Canadian rapper Drake partnered with the online casino Stake.com in 2022. Drake had been gambling and expressing interest in the platform before the partnership was made official. He remains a partner with the brand two years later — and if that doesn’t signify a passion for gambling, what does?

5. Frank Sinatra

Frank Sinatra is a name most of us recognize; he gave the world classic and beloved songs like “Fly Me to the Moon” and “The Way You Look Tonight,” but what many don’t know is that the singer’s passion for Vegas was not just rooted in performing but also gambling there.

He loved it so much that he even owned a casino, the Cal Neva Lodge and Casino. However, he lost his gaming license after being accused of stealing money and being linked to organized crime characters (he often faced accusations of mob ties during his career).

6. 50 Cent

The famous rapper, actor, producer, and entrepreneur 50 Cent (whose legal name is Curtis James Jackson) is widely known for his talent and collaborations with major players in the rap and hip-hop world, like Eminem, Dr. Dre, Lloyd Banks, and Snoop Dogg, just to name a few. He even found his way back to success and riches after filing for bankruptcy in 2015.

What’s less known is that in addition to being a multi-talented creative, he also has a huge interest in gambling. He’s been reported to take part in high-stakes sports betting and has even created a Facebook blackjack game.

7. Diddy

The rapper and producer known by many names, including Diddy, P Diddy, Puff Daddy, and Sean Combs, is also known to be a huge fan of table games. However, his connection with casinos hasn’t been without drama. In 2010, an Atlantic City Casino had to shut down when a crowd hoping to party with the rapper got too rowdy. He’s even shared that he’s won $2 million in Vegas and, as a result, gave a $250,000 tip to the game’s dealer.

8. Ian Kilmister

Ian Kilmister, better known as “Lemmy,” the lead singer and bassist of Motorhead, was a big fan of gambling — a fact that isn’t surprising considering the fast-paced, risk-taking, and wild life he led. He would often be found at card tables when he wasn’t writing or performing music. His love for gambling even came through in one of Motorhead’s biggest songs, “Ace of Spades.”

9. Harry Styles

While One Direction was still together and touring, Harry Styles was known to visit the casino and try his luck with table games. While his management team was not a fan of this, reportedly giving him a “dressing down“ the first time it happened, this didn’t stop him from heading to the casino floor again while still on tour a short time later.

10. Jay-Z

Shawn Corey Carter, more commonly known as Jay-Z, is an influential rapper and producer. He’s also husband to the icon Beyonce, and the two together are nothing short of a power couple in the music industry and beyond. A little-known fact about Jay-Z is that he loves gambling, though he’s more private about it than the other stars on this list. Or at least, that was the case until about a year ago.

In May 2023, Jay-Z made his interest in the gambling world known by adding his name to the running to bring a casino to Times Square, New York. The competition is fierce, as it is anticipated that only one gaming license will be approved for the city. Currently, four other New York City billionaires are also hoping to earn a place in the city’s soon-to-be-booming gambling scene.

The Fun of the Gamble Is Always Appealing

These musicians show that even when you make it big, the glitz, glamour, and thrill of gambling still has its appeal.