Four big-winning celebrity gamblers

From the outside looking in, it would appear as though celebrities – during an age in which their type are lauded as some form of human deity – are already very much winners at life.

Entire teams of staff are assembled to cater to their every whim – they are dressed, pampered and revered to within an inch of their life.

Good looks, money in the bank and a job that requires you to talk in front of a camera, sing into a microphone or chase around after a ball, some people seemingly have it all.

Even when the spotlight begins to fade slightly, those in the ‘business’ can console themselves in the knowledge that there will always be a place for them eating spiders in the Australian jungle or swearing loudly at fellow has-beens in the Big Brother house.

Life, it would appear, is pretty rosy for the social elite.

Some people, though, want it all, refusing to accept that they have it about as good as it gets and, wouldn’t you just know it, Lady Luck is often on their side then, too.

Here are four celebrities – but a drop in a much larger ocean – who like to win big in all walks of life.

ben affleck casino

Ben Affleck: Oscar-winning, J-Lo-dating, Jennifer Garner-marrying, Affleck is about as A-list as they come. You would think that someone so enveloped by the Hollywood lifestyle would find it difficult to drag himself away from the glitz and glam, with life one big pool party in the Los Angeles hills. Millions of bucks taken from the movie business is not enough for the Gone Girl star, though, as he is known to be partial to the odd casino visit. And who can blame him? Affleck was reportedly barred from the tables of the Hard Rock Hotel in Las Vegas after embarking on an eye-watering winning streak. Betting $60,000 per hand at blackjack, he is said to have walked away with $800,000 in winnings – even after tipping the dealers $150,000. Well you would, wouldn’t you!

Ashton Kutcher

Ashton Kutcher: From the catwalk to the big screen, Demi Moore to Mila Kunis, you get the feeling that Kutcher could tumble head first into a slurry pit and come up smelling of roses. His luck is not restricted to his professional and personal life either, he even manages to score big on the hobby front. A renowned sports fan, one who can often be spotted court side at LA Lakers home games, Kutcher once made $750,000 in a single month as the head of a college football syndicate, placing bets for professionals who knew how to beat the system. He told Esquire Magazine what happened.

50 Cent

50 Cent: It should, perhaps, come as no great surprise to learn that a paid up member of the hip-hop community – one who is named after an American unit of currency – embraces every opportunity he gets to line his pockets. Rappers like the finer things in life, and they don’t come cheap. Money has to be made somewhere, and for Curtis Jackson that quest has taken him to the recording studio, the film set and the bookies. Mr Cent is known for having the odd flutter, and he doesn’t do things by halves when the mood takes him. He landed a cool $1 million in cash after betting on Floyd Mayweather’s super fight with Oscar de la Hoya, while he also banked $500,000 predicting the outcome of an NFC Championship game between the San Francisco 49ers and New York Giants in 2012. He admitted after that success to having ‘followed the voices in his head’. Why don’t the voices in our head offer such useful information?

Teddy Sheringham playing poker

Teddy Sheringham: We may be breaking from the Hollywood trend slightly here, but Teddy Sheringham was once about as showbiz as a professional footballer / soccer player gets. He may not be in the David Beckham/Cristiano Ronaldo bracket, but he is still a figure who transcends the sport that made him famous. For a long time the former England international was more accustomed to being the subject of wagers, with punters on exchanges such as those at betfair placing their trust and hard-earned cash on him doing the business on the field for the likes of Manchester United, Tottenham Hotspur and West Ham United in the English Premier League. Nowadays, while back in the game as manager of Stevenage, Sheringham has been known to dabble in the profitable world of poker. He has won close to £250,000 in live tournament events, has competed in two World Series of Poker and once collected €93,121 from a single contest in Vilamoura. Not a bad day’s work!