15 Times Music Celebrities Were Caught at the Casino

Some of the most famous music stars have been drawn into the casino scene, a place full of excitement and high stakes. With all the fame and fortune, it’s no surprise that some have found themselves at the tables, taking their chances. For some, it’s been a lighthearted thrill. For others, it’s brought serious challenges and stories that highlight the risks involved.

Here, you’ll find a look at fifteen celebrities whose casino experiences left a mark on their lives and careers. Each story reveals a side of fame that’s rarely seen, where the glamour of celebrity meets the unpredictable world of high-stakes gambling.

1. Nelly

Nelly, the rapper who brought hits like “Hot in Herre” and “Ride wit Me,” had an impressive rise to fame.

Yet behind the success, rumors circulated about his struggles with gambling. In 2011, his former promoter publicly claimed that Nelly had lost significant sums at casinos, hinting at deeper financial troubles.

While Nelly has often kept his private life away from the spotlight, these claims painted a different picture, one where fame’s pressures led him toward high-stakes tables.

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2.  Gladys Knight

Gladys Knight, known to fans as the “Empress of Soul,” has always been admired for her incredible talent and resilience.

In her autobiography, Between Each Line of Pain and Glory, Knight shared details of a gambling problem she battled for nearly ten years. Baccarat became her game of choice, and she described how it became a habit that was tough to break.

The revelation shocked some fans, as it highlighted a side of her life she had kept hidden for a long time.

3.  Ray Romano

Ray Romano may be best known for making audiences laugh, but his personal life hasn’t always been light-hearted.

The actor and comedian has openly shared stories about his past gambling struggles, which even inspired part of his character’s journey on the show Men of a Certain Age.

Romano’s interest in gambling began casually, but over time, it became something he had to actively work on leaving behind.

4.  Michael Phelps

Michael Phelps, known around the world as the most decorated Olympian, occasionally found himself drawn to the casino scene.

While he hasn’t been caught up in any official gambling scandals, there were enough reports of his frequent visits to Las Vegas to raise eyebrows.

Friends expressed concerns over how often he seemed to be at the tables after retiring from competitive swimming. For someone used to intense training and high-pressure races, the draw of a casino seemed to offer a similar adrenaline boost.

5.  Charlie Sheen

Charlie Sheen’s public life has been as turbulent as his career has been iconic. Known for his acting work and connections in music, Sheen faced allegations of gambling large amounts during his marriage to Denise Richards.

During their 2006 divorce, Richards claimed Sheen regularly placed high-stakes sports bets, with some amounts reportedly hitting hundreds of thousands of dollars.

6.  Ben Affleck

Ben Affleck’s love for blackjack isn’t just a rumor—it’s well-known in Las Vegas circles. In 2014, he made headlines when the Hard Rock Hotel & Casino asked him to stop playing blackjack due to his impressive skills.

Security reportedly flagged him for “card-counting,” a strategy that’s not illegal but highly discouraged by casinos.

Affleck admitted he loved the challenge of the game, and his time at the tables brought him both attention and a reputation as a serious blackjack player who knew how to gain an edge.

7.  Tobey Maguire

Tobey Maguire’s connection to high-stakes poker went public in 2011 when he was named in a lawsuit for participating in underground poker games.

These games, held in exclusive locations across Los Angeles, involved other celebrities and wealthy players betting big money.

Maguire became known for his poker skills, but his involvement in the illegal games ended up landing him in legal trouble.

8.  Shannon Elizabeth

Shannon Elizabeth didn’t just dabble in poker—she dove into the game as a serious pursuit. Known for her talent at the poker table, she’s been spotted competing in multiple casino poker tournaments.

Elizabeth’s frequent appearances in poker rooms across Las Vegas and her reputation as a skilled player made her a fixture in the casino scene.

Unlike other celebrities who gambled casually, she took it on as a second career, bringing a professional edge to her time at the tables.

9.  Michael Jordan

Michael Jordan’s gambling habits often brought him to the casino tables, especially during his off-seasons. He became known for high-stakes bets on card games, both in casinos and in private settings.

Reports of his frequent visits to Atlantic City’s casinos during the 1990s, even on the nights before games, became the subject of intense media focus, which is quite common thing among NBA players.

10.  Phil Mickelson

Phil Mickelson’s reputation as a gambler has included numerous appearances in Las Vegas casinos and other betting environments. Known for his strategic mind in golf, Mickelson brought that same energy to gambling.

His time in casinos often centered on sports betting, but he was also seen at the card tables placing substantial wagers.

11.  Drake

Drake has become known not only for his music but also for his high-stakes bets, often posting about them online. He’s been spotted placing large wagers in casinos, especially in Las Vegas, and he’s known for betting on sports games with serious amounts of cash.

One of his more publicized gambling moments involved a bet on a high-profile fight where he reportedly lost over $500,000.

12. William Hung

 

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William Hung, famous for his appearance on American Idol, later found himself dealing with gambling issues that impacted his finances.

Hung has been spotted at various casinos, where he reportedly lost significant amounts. His gambling struggles became public when he was seen promoting a gambling website on his way back from Las Vegas, sparking concern about his relationship with betting.

13.  Norm Macdonald

Though primarily known as a comedian, Norm Macdonald has long been open about his love for gambling, which included regular trips to casinos.

Macdonald was often seen placing big bets at casinos, where he once lost over $400,000 in a single sitting. He spoke candidly about his attraction to the rush of the casino floor, and his losses became as much a part of his life story as his stand-up routines.

14.  Brendan Fevola

Brendan Fevola, while famous for his sports career in Australia, is also known for his repeated appearances in casinos, particularly on the betting floor.

Reports of his gambling habits include massive losses, with some estimates suggesting he lost close to a million dollars over the years.

Fevola’s most publicized casino moment involved him betting hundreds of thousands on horse racing in a single day.

15.  Bruno Mars

Bruno Mars has been linked to gambling rumors, particularly involving his extended Las Vegas residency.

Though reports of a supposed $50 million gambling debt were denied by his representatives, Mars has been spotted at the casino tables multiple times during his stay in Vegas.

His regular presence in casinos has fueled stories about his interest in high-stakes gaming.

Last Words

Gambling pulled each of these celebrities into unforgettable moments, some leaving with more than they bargained for, and others facing losses that hit hard.

The casino floor and poker tables saw their highs and lows—glimpses of the real lives behind their public faces. For some, gambling added excitement; for others, it brought challenges they didn’t expect.