Famous Celebrities Investing in Casinos: Hollywood’s Hidden High Rollers
From glamorous parties to high-rolling poker tables, celebrities have often been drawn to the thrill of gaming.
But for some, the appeal goes far beyond just playing; they’ve stepped into ownership roles, investing their star power and fortune into casino ventures.
Here’s a look at a few famous faces from screen and stage who have tried their chances in the casino industry.
George Clooney – Las Ramblas Resort
In the mid-2000s, Hollywood icon George Clooney set his sights on the Las Vegas Strip with plans to open the Las Ramblas Resort, a luxury hotel and casino.
Clooney partnered with entertainment executive Rande Gerber and developers from Centra Properties to bring his vision to life, a chic, European-inspired resort that would blend high-end hospitality with the classic charm of Vegas nightlife.
However, despite its ambitious design and Clooney’s star appeal, the project ultimately never broke ground due to financial and market challenges. Still, Las Ramblas remains a fascinating “what could have been” story in the history of celebrity casino ventures.
Bruce Willis, Sylvester Stallone, and Arnold Schwarzenegger – Planet Hollywood
Three of Hollywood’s biggest action heroes, Bruce Willis, Sylvester Stallone, and Arnold Schwarzenegger, joined forces in the 1990s to bring their blockbuster appeal to the hospitality scene with Planet Hollywood. While best known for its restaurant chain filled with movie memorabilia, the brand eventually expanded into the casino business.
The Planet Hollywood Resort & Casino in Las Vegas became a hub of star-studded energy, blending Hollywood glamour with Vegas excitement. Although the celebrity trio eventually divested from the company, their involvement helped define Planet Hollywood’s early success and gave it a pop-culture edge that still resonates today.
Tobey Maguire – Hollywood Park Casino
Tobey Maguire, known for his portrayal of Spider-Man, has long had a passion for poker. His skills at the card table are almost as famous as his acting career; he was even a central figure in the real-life high-stakes poker games that inspired the film Molly’s Game.
Maguire later extended that passion into ownership with a stake in Hollywood Park Casino in Inglewood, California. The venue, known for its poker and table games, became a natural fit for Maguire’s interests and connections in the gaming world.
Ben Affleck – Hard Rock Hotel & Casino
Oscar-winning actor and director Ben Affleck is another Hollywood star who has merged his love of cards with business. Known for his prowess in blackjack, he’s even been reported to have been “too good” for certain tables. Affleck took a financial interest in the Hard Rock Hotel & Casino in Las Vegas.
The Hard Rock brand is synonymous with music, nightlife, and celebrity culture, and Affleck’s involvement underscored his deep ties to the entertainment scene. His business ventures in the casino world reflected his dual love of gaming and hospitality.
Frank Sinatra – Cal Neva Lodge & Casino
Long before modern-day celebrity investors, there was Frank Sinatra, one of the first stars to truly embrace the casino business. In the 1960s, Sinatra became part-owner of the Cal Neva Lodge & Casino, a glamorous retreat located on the shores of Lake Tahoe.
The venue was a hotspot for Hollywood’s elite and political figures, from Marilyn Monroe to members of the Kennedy family. However, Sinatra’s ownership came to an end after his alleged connections to organised crime drew unwanted attention from regulators.
Still, Cal Neva remains an iconic piece of casino and entertainment history, with Sinatra’s legacy forever intertwined with its storied past.
Jay Z – D’Usse Lounge At The Cosmopolitan
Though not a casino owner in the strictest sense, Jay-Z is a prime example of a star who has leveraged his brand and business acumen into ventures that intersect with casino culture and nightlife. One such venture is the D’USSE Lounge at The Cosmopolitan in Las Vegas.
D’USSE is Jay-Z’s cognac brand, co-launched with Bacardi. The branded lounge space is attached to this major casino resort and serves more than just drinks. It’s part of the overall entertainment area, providing guests with a place to enjoy premium spirits and socialise as part of the entertainment circuit inside the casino resort.
Why Celebrities Get Involved
There are a few recurring reasons stars choose to invest in or link their name to casinos, lounges, or resort gaming. Brand alignment can be a big factor with casinos offering luxury entertainment and a nightlife-heavy culture. For many stars, this aligns well with their image.
It can also be a way of diversifying their portfolios. After all, entertainment incomes can be volatile, so investing in real estate, hospitality, or physical venues adds different revenue streams. There is also a level of prestige and legacy that comes with these types of ventures, with some stars viewing these investments as part of their lasting cultural footprint.
**The information provided in this blog is intended for educational purposes and should not be construed as betting advice or a guarantee of success. Always gamble responsibly.