Gambling with Fame: When Celebs Hit the Casino

In many ways being a popular celebrity is already coming up a winner. Having the talent, luck, and/or looks to succeed in industries with such massive competition is a feat few will ever accomplish, but many aren’t happy to leave their fortune there. With this in mind, we want to take a look at some of the biggest success stories in celebrity gambling, to see who can back up their fame at the tables.

The Best Bond

We don’t want to start a fight, especially in terms of acting, but when it comes to who represents Bond’s luck; there is nobody better than Sean Connery. During a stay in a casino located within the Italian Alps in 1963, Connery decided to test his ‘Bondishness’ at the roulette table. Apparently having a vision, he placed his bet on 17.

While his first best came up a bust, he stuck it out. What eventually followed were three winning consecutive bets on lucky 17, after which Connery gave up on tempting fate. According to the dreaded monster also known as probability math, the odds of this particular line of fortune come in at around 50,000/1.

Sean Connery as James Bond” (CC BY-SA 2.0) by johanoomen

We may be jealous of his ability to channel his character’s fortune, but at least the beauty of roulette means we can try ourselves from home. Sure, we don’t have Bond’s movie-star luck, but at least having access to a variety of online roulette games, like live roulette, means we can give it go without the associated costs of travelling to exotic countries, and risking our lives at the hands of maniacal villains with gold teeth.

Professional Skill

Gambling is largely about luck, true, but it also relies on an element of skill. It is this skill which famed Chuckie actress Jennifer Tilly works with as she plays her way through the World Series of Poker circuit. While she focuses primarily on Hold’em, Tilly’s talent reaches into most other poker forms, as she and her husband, the similarly poker-skilled Phil Laak, consistently play among the best.

Having taken home over $750k in winnings so far, including a single win of $158k, this lady’s killer attitude is far from the ditzy affectation which made her famous. If you ever play a game with the smoky-voiced beauty then beware, you’re probably about to lose.

Jennifer Tilly” (CC BY-ND 2.0) by World Poker Tour

A Million Percent Growth

50 Cent is no stranger to gambling and big money, which flies in direct opposition to his rap name. As a New York native, Cent was a big supporter of the New York Giants, who he bet on to be the final victors in Super Bowl 46.

Taking home the gold with a 21-17 lead, 50 netted himself a cool $500k, also known as a million fifty-cent pieces. Not happy to rest on those laurels, 50 followed this up with a double or nothing, with another win bringing him home an additional $500k.

50 Cent TigerDirect Appearance” (CC BY-ND 2.0) by

Looking at these wins we have to wonder, which would we rather take; success as a celebrity or success as a gambler? While the two might not be mutually exclusive, we have to say that, given the opportunity, we would be happy with either.

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