10 of the Best (and worst) Celebrity Gamblers

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Gambling isn’t just for those who want to get rich, there are loads of flush celebrities trying their hand in the casino. Seems kind of backwards when you think about it. Why would somebody with millions of dollars in the bank want to risk it all to make a bit of extra cash?

Poker is generally the game of choice for the majority of our celebrity gamblers, but some like blackjack and even a couple are inclined to dabble at the bookies. Whatever they play it’s usually with big bucks. We’re not talking about a few dollars here or there, we’re talking about $10k spins and $60k hands.

With some celebrities racking up $60 million worth of losses, it just goes to show that if you don’t gamble smart you’ll lose big. We’ve got a feeling that a Lucky Nugget gaming guide could have saved them a lot of cash.

Here’s 10 of the very best (and some of the worst) celebrity gamblers we could find. Honestly, you’ll be surprised about some of the names that crop up – possibly.

Charlie Sheen

Claimed to be winning – lost $200k a week gambling. Some will know him from his successful acting career and others from his days as a raging alcoholic with drug issues. Fortunately, it looks like he’s got over the drugs and alcohol, but we’re guessing his gambling losses still sting to this day.

What was his game of choice?

Charlie Sheen was a fan of the bookies but has also been known to dabble in the casino from time to time. With the $1.8 million he was making per episode from Two and a Half Men, he could easily afford it.

Was Charlie Sheen a good gambler?

In his altered state we reckon he couldn’t differentiate between red and black, so probably not. Nothing has been reported about his wins though and he’s a little bit of a genius so maybe he actually busted the casino – probably not.

John Daly

One of the hardest drivers in golf, it’s a shame he hit the casinos just as hard. Overall John Daly gambled over $90 million from tour winnings and sponsorship deals. It is rumoured he managed to recuperate $35 million, resulting in a net loss of $65 million. That’s still quite a hefty amount.

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What was his game of choice?

Blackjack.

Daly was a big fan of blackjack playing 7 hands at a time. People used to crowd around to egg the big man on, but it did him no good. If only somebody would have put a hand on his shoulder (or maybe a Lucky Nugget blackjack guide) he might have come out a little bit richer on the other side.

Was John Daly a good gambler?

No. He lost $60 million.

John Daly was a dreadful blackjack player.

Floyd Mayweather, Jr.

Now for somebody who knows how to gamble. Floyd Mayweather, Jr. – as you probably well know – is an American boxer and business magnate. He’s rather boring to watch but he’s undefeated and as such has a rather large profile. He’s not one to shy away from a challenge and for no reason other than to boast he likes to stake extraordinary amounts of money on sport bets – he’s a bit of a show off.

Floyd-Mayweather

What’s his game of choice?

Sport betting.

It’s safe to say he’s gambling mad. The $11 million he spent on a single Denver Broncos match certainly suggests he enjoys dabbling at the bookies. Floyd Mayweather is known for exaggerating his winnings slightly though and the $6.49 million he picked up in winnings could be somewhat inflated.

How good is Mayweather at gambling?

Yes, much better than John Daly.

Mayweather doesn’t advertise his losses, unfortunately, so we don’t really know if he’s up or down. We’re guessing he’s up because he seems like a smart bloke.

Qui-Gon Jinn

Jedi Master and foolish enough to think that Anakin Skywalker would be a goody, Qui-Gon Jinn manages to snatch Skywalker away from Watto in The Phantom Menace with a gentlemen’s bet.

What was his game of choice?

The only way Qui-Gon could ever save Skywalker was through a simple bet on pod racing. If Anakin won, he would go free – if he didn’t, Qui-Gon would lose his ship to Watto. Never in doubt, Anakin somehow managed to cross the line and seal his fate as the biggest baddy ever.

Was he any good?

It was the only bet he ever placed and he won – that’s a 100% success rate. Can’t argue with that.

Derren Brown

The famous magician/illusionist/wizard from London, England is rather famous for his mind-boggling tricks and illusions. Derren Brown is probably most famous for guessing the results of the National Lottery in England, which back then was a pick 6 from 49 style game. The odds of him correctly choosing six numbers was around 14 million to 1 – so yeah, it was a pretty magical event.

What’s his game of choice?

Derren Brown is quite the smart bloke and before he kicked off as a career magician he was a rather successful blackjack player; so good that he never lost a hand. Now, casinos don’t really like you constantly win and so Derren was slowly banned from every British casino. He got away with it for a while, though, betting small and infrequently, but soon pit bosses started to recognise his face and even subtle disguises couldn’t fool casino security.

Unfortunately, his casino days were over but his career as a magician had just started.

Was Derren any good at gambling?

Well, he never lost. Magic was most definitely on his side though and that’s going to boost your odds a little. We’ve always wondered if Merlin would have been a good gambler and now we know.

Ben Affleck

The words ‘gambling’ and ‘Ben Affleck’ are commonly found in the same sentence nowadays. Whether it’s blackjack or poker, he’s going to be in the news for one reason or another. His recent split from Jennifer Garner is reported to have been caused by his gambling vices; as far as we can tell he was pretty good at the old game.

What’s Affleck’s game of choice?

Often found at the poker table, Affleck has gained quite the reputation with fellow celebrity and Casino star James Woods complimenting his fierce poker skills.

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Whether Affleck gets his practice in playing video poker remains to be seen but it must be said should the acting dry up Affleck could have a second career as a poker pro.

He’s also a big fan – like most celebs – of blackjack. Like Derren, he’s been banned for card counting and can’t find his way into one anymore. Guess that’s the problem when you have a recognisable face.

Was Affleck any good?

Well, he’s won more than $300,000 playing poker so he can’t be that bad. It’s not really about the money for Affleck, he’s got plenty of it. It’s about winning.

Queen Elizabeth

Imagine that, the Queen of England dabbling on the horses. She owns a few don’t you know, and she can be found trackside for most major events. When her horse Free Agent flew past the field in the final three furlongs and won the race, she jumped out of her seat with joy – how quaint.

What’s her game of choice?

Keno – only kidding. Her Majesty will have the occasional bet on her horses, but that’s about it. She’s not one to rock up at the bookies on a Sunday so don’t wait for her to stumble in – she’s far too posh for that.

Is she any good?

Unfortunately, we can’t give Buckingham Palace a bell, which is a shame, but we reckon she’s not too bad. She knows her horses well and has owned a few winners over the years, so yeah, we reckon she’s pretty good.

Marge Simpson

The loveable over half of Homer Simpson and star of the hit US television show The Simpsons, Marge is often regarded as the saint of Springfield.

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What was Marge’s game of choice?

When the casino arrived in one of the most famous episodes $pringfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling) – Marge develops a love of all things slots, becoming an overnight master.

Was Marge any good?

She immediately won her first game and so luck was definitely on her side. After that, she didn’t do too well presumably losing quite a bit. Fortunately, Homer defeated Gamblor and snatched her back, otherwise she’d probably still be there now.

Gladys Knight

The ‘Empress of Soul’, Gladys Knight is an American recording artist, businesswoman, author and big- time gambler. Well, she was a big-time gambler, not anymore. Something to do with spending shed loads of money and ignoring her kids.

What was her game of choice?

Blackjack – $40,000 a night. She was gigging at a casino one night and a friend introduced her to the famous table game and from that point on she was hooked. Enthralled in blackjack, her lowest point was when she should’ve been at home sorting her kids out for school but instead was still gambling – fortunately she’s over that now.

Was she any good?

Not really – she lost track of time and let the game take over her life. If you’re smart and safe that’s fine but Gladys sure was not.

Tiger Woods

Another golfer, another turbulent life; Tiger Woods’ rollercoaster life has been well documented by the press.

With a net worth of around $600 million, he’s certainly had one of the most successful careers in golf, but he’s not immune to the vices that regular people fall victim to. He was back in the headlines around 2009, not for golfing but for cheating on Elin Nordegren. From that point on Tiger’s life has been a bit rocky.

What was his game of choice?

Again, it’s blackjack, which seems to be the game of choice for the wealthy and famous. It was one thing he couldn’t cheat on and as such he ended up losing around $25,000 a hand, although some report that the golfer bets up to $200,000 at his lowest moments – ouch!

Was he any good?

Nope, these celebrities really need to start using our blackjack guide – it could save the likes of Woods and Daly millions.