Hollywood Hold'Em: Celebrities and Gambling

Duncan Wilkie. - July 18, 2016
Hollywood Hold'Em: Celebrities and Gambling

It might not come as a surprise to anyone that many celebrities like gambling; actors and athletes alike. Let's take a closer look at some of the more interesting gambling stories from the world of glitz and glamour.

Whether it’s down to the huge amount of disposable income that comes as part and parcel of the Hollywood lifestyle or the need to let off some steam away from the prying eyes of the paparazzi, there can be no denying there are plenty of big-name celebrities who enjoy the occasional flutter.

Indeed, with the leisure habits of the rich and famous seemingly intrinsically linked with gambling – particularly during the poker boom years of 2003-2006 – you only have to turn on your television after the watershed to find evidence of household names playing for the highest stakes imaginable.

Of course, this fascination with gambling is a two-way street, with the celebrities who indulge in it easily having the money to spare and we – the public – having a willingness to see them gamble. As such, a culture of entertainment has evolved where we can live vicariously through our idols, sharing in their triumphs and feeling the pain of their losses; all from the comfort of our own living rooms.

In this article, we’ll take a closer look at some of the prominent personalities who are known to have enjoyed the odd bankroll-busting wager, along with the ways in which media coverage has allowed us a glimpse into their world. Join us, then, as we run the rule over celebrities who love to gamble.

The Cult Of Personality

While celebrities have been gambling for virtually as long as casinos have existed, our interest in their leisure activities is something of a recent development. These days, sports stars and Hollywood A-listers can’t so much as go grocery shopping without being snapped by the press, so it should come as little surprise that when they sit down at the gaming tables, the cameras are usually rolling.

This has been evident since the turn of the millennium, when TV channels such as Bravo and the Game Show Network started broadcasting star-centric gambling shows Celebrity Poker Showdown and Celebrity Blackjack respectively. Though imitated by other networks and gambling companies many times since, these shows were undoubtedly the start of our love affair with celebrity gambling.

Over the years, tournament winners on Celebrity Poker Showdown have included US comedian Jason Alexander and talk-show host Seth Meyers, while through two seasons of Celebrity Blackjack we witnessed reality TV star Caroline Rhea and director Dean Cain both donate their winnings to charity.

The significance of the viewing figures attached to these two pioneering shows wasn’t lost on TV executives, who began commissioning a number of similarly-themed shows such as E!’s Hollywood Hold’em and CBS’s Celebrity Poker Live. Similarly, a number of poker sites also saw the drawing power of celebrity players, with many stars named as brand ambassadors in the years that followed.


Hollywood Hold’Em

Though by no means the only gambling sector that has been inundated with celebrity players in recent years, poker is undoubtedly the industry that has seen the most growth thanks to Hollywood endorsement. Seen as the “hip” thing to do for much of the early noughties, the annual World Series of Poker in Las Vegas has since seen a who’s who of famous faces flock to the Rio every summer.

One of the most significant factors leading to this trend was the release of the hit poker movie Rounders in 1998. Starring Matt Damon and Edward Norton – both of whom would learn the game of Texas Hold’em and regularly participate in the WSOP in the years that followed – the film brought poker to a mainstream audience and showed celebrities this was a new fad they could participate in.

Since the film’s release, the aforementioned Jason Alexander has regularly ponied up the $10,000 entry fee required to play the tournament, as have American Pie actress Shannon Elizabeth, Everyone Loves Raymond  stars Brad Garrett and Ray Romano, Hollywood A-listers Ben Affleck and Toby Maguire and silver screen icon, James Woods, who is now the public face of Hollywood Poker.

Though their levels of ability and success stories vary wildly, Woods ($216,228 in tracked career cashes) Elizabeth ($235,866) and Affleck ($356,400) have all done remarkably well from poker over the years, while Maguire – who benefitted from the coaching of Canadian poker pro Daniel Negreanu –  has also reportedly won large sums in the private home games organised Molly Bloom. Mark Wahlberg is famous for losing $45,000 on a single roulette bet in a Macau casino, a bet which he had taken while preparing for his role in the 2014 movie “The Gambler” where he portrays a literature professor with a gambling problem.

Given A Sporting Chance

While world-renowned football stars Ronaldo and his Portuguese namesake Cristiano have gone on to become prominent figureheads for online gaming giants PokerStars, it is not just Texas Hold’em that attracts celebrity gamblers. Indeed, while sports betting may be off the table for most athletes, casino visits are seen as a good way to let off steam and many players take advantage of this fact.

One of the most notorious sporting celebrity gamblers in recent years has undoubtedly been US golfer Tiger Woods, who is known to have been awarded a $1 million credit limit by the MGM Grand in Las Vegas. Reportedly favouring high-stakes blackjack, Woods is alleged to have bet up to $25,000 a hand and is also good friends with fellow sporting gamblers Michael Jordan and Charles Barkley.

Another high-profile betting enthusiast is Floyd Mayweather Jr, who is thought to have once won $3 million betting on college football. The professional boxer is certainly no stranger to playing for nose-bleed stakes, with several media sources reporting that he regularly bets upwards of $400,000 per sporting event and one sensationally claiming he placed a $10 million bet on Super Bowl XLVIII.

In the UK, meanwhile, casino gambling has long been a favoured pastime of the Premier League elite, with stars like Mario Balotelli and Samir Nasri being pictured at high-end venues in recent times and the author of this blog personally witnessing several members of the 2013/2014 Newcastle United squad getting their kicks around the blackjack tables at Aspers Casino at The Gate.

Given the huge amount of pressure that comes with being a professional sportsperson or an actor in the constant glare of the media spotlight, it is perhaps little surprise that celebrities frequently find themselves in poker rooms and casinos the world over. After all, with the vices like smoking and drinking shared by us mere mortals being out of the question for any serious professional, what else are they to do with their time other than put their money where their mouth is and hit the tables?



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