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Eight Celebrity Views on Gambling

Published on October 25, 2014, 4:32 pm

by Jeff Grant Twitter account Jeff Grant LinkedIn account

This December, pop star Britney Spears will begin a two-year stint in Las Vegas performing her new show, “Britney: Piece of Me”. Entertainment authorities expect the upcoming Planet Hollywood feature to be one of the hottest-selling Vegas shows of all time (click for infos). Spears is currently contracted to perform 48 shows per year for a total of almost 100 shows.

Each performance will net her $300,000, earning the pop diva millions of dollars. Gamblers shouldn't expect to see Spears at the Planet Hollywood tables or on the floor, however; the singer recently proclaimed to the public that she “hates” gambling and would rather spend her money on shoes.

Spears is not the first person to dislike gambling, but her disdain for the activity makes her stand out in the celebrity world. Whereas Spears prefers to shop until she drops at high end department stores, the following seven celebrities have demonstrated a preference for wagering activities:

Tiger Woods: Over-the-Top Blackjack Bets

Professional poker player Tiger Woods
Tiger Woods

Scandalous golf star Tiger Woods, known for his extramarital affairs with an excessive number of women, apparently has a penchant for excessive blackjack betting as well. Woods purportedly bet around $25,000 a hand on blackjack during a gambling binge at MGM Las Vegas in 2009, according to former mistress Jamie Jungers. Accompanying Woods and Jungers on the spree was Charles Barkley, a retired pro basketball player with a reputation for compulsive gambling.

Charles Barkley: Compulsive Gambler

Retired basketball star Charles Barkley
Charles Barkley

Retired basketball star Barkley admits he has a problem with gambling addiction. In the same breath, he acknowledges the fact that he's flush with the funds to support his habit. An ESPN interview with the athlete revealed that he has lost approximately $10 million to gambling over the course of his lifetime. Although Barkley has had some casino wins, such as the $700,000 jackpot he once took home after a night of high-stakes blackjack, his overall gambling scorecard is not anywhere near as successful as his athletic record.

In 2008, Barkley was sued by Wynn Las Vegas over $400,000 in bad check charges, which translates into unpaid house credit debts. In 2012, Barkley poked fun of his own gambling habit on the year's premier episode of Saturday Night Live. In spite of his notorious gambling losses, the athlete continues to project the image of a man who can handle his enormous financial losses.

Ben Affleck: A History of Gambling Rehab

Actor Ben Affleck
Ben Affleck

In 2001, actor Ben Affleck called his friend Charlie Sheen and asked him to drive him to a gambling rehab center where comedienne Paula Poundstone was also in residence. This happened one day after Affleck had gambled the previous night away at Hard Rock Hotel and Casino, betting up to $60,000 a hand at blackjack beside his friend Matt Damon.

Today, twelve years later, Affleck stars alongside Justin Timberlake in a soon-to-be-released gambling film called "Runner, Runner". The film tells an intriguing story of online gambling corruption which some gaming organizations are hoping will lead to tighter online regulations. It was reported that the recovering star avoided Timberlake socially during the making of the film in order to say clean and avoid falling back into old behavior patterns.

Ray Romano: “Comedians Make Bad Poker Players”

Comedian Ray Romano
Ray Romano

Comedian Ray Romano has stated that comedians make bad poker players because they want everybody to love them. Interestingly, Romano battled a gambling addiction in his earlier years that ultimately sent him to Gamblers Anonymous. Between 2009-2011, Romano played a gambling-addicted character in a TNT sitcom called "Men of a Certain Age."

After the show was canceled, Romano went back to doing stand-up comedy. In spite of his past addiction and his quip that comedians make bad poker players, Romano participates regularly in the World Series of Poker.

Brad Garrett: Poker for Charity

Comedian Brad Garrett
Brad Garrett

Comedian Brad Garrett, who starred alongside Romano in Everybody Loves Raymond, is a poker player with a conscience. In 2012, Garrett hosted an all-star poker tournament at MGM Las Vegas which raised $112,000 for the Maximum Hope Foundation, a charity organization founded by Garrett.

The Maximum Hope Foundation, named after Garrett's two children, Max and Hope, grants financial assistance to the families of kids with life-limiting illnesses.

Pamela Anderson: Paid Her Gambling Deb With Sexual Favors

Pamela Anderson
Pamela Anderson

In 2007, Pamela Anderson found herself in debt and out of money at a poker table. She admitted to Ellen Degeneres that she allowed an unnamed gentleman to pay off her debt, about a quarter of a million dollars, in exchange for sexual favors.

A year before that, Anderson had tried for four months to establish her own online poker site. The site failed even as Anderson admitted to the public that she didn't really know what she was doing. Today, seven years later, Anderson is the buxom mascot for, a free Facebook poker app.

Michael Phelps: World Series of Poker 2013

Retired gold medalist Michael Phelps
Michael Phelps

Retired gold medalist Michael Phelps not only swims with gusto, he also gambles with gusto. For years, sources have speculated that Phelps has a gambling problem. One source claimed that the Olympic swimmer was in danger of losing “millions” to his out-of-control poker habit. In 2013, Phelps garnered attention by attending the World Series of Poker.

This wasn't his first gambling experience; in 2008, Phelps won over five thousand dollars at the Caesars Palace Classic. Whether Phelps' poker record will become as notorious as his swimming record remains to be seen.


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