There’s an old saying suggesting that you should never bet against friends, but in the end many people still insist on doing so – including celebrities. The best wagers of all time generally involve famous starts, because they play with high stakes.
We have found some interesting wagers between celebrities, some involving poker rings, blackjack, and sporting wagers, as well as some others seeing interesting side bets that have made headlines. We’ve also included some advice at the bottom when it comes to betting against your friends, and the best casinos to gamble online.
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High stakes poker bets
Attended by celebrities such as Leonardo DiCaprio, Tobey Maguire, and Ben Affleck, high stake poker rings hosted by Molly Bloom were once a regular occurrence for these stars. With buy-ins of around $100,000 the poker ring featured some high stake bets against each other which would send us bankrupt. Not for these stars, who are all in fact friends, and six digit bets against each other were standard. However, it was discovered these rings were a part of the illegal underground poker ring scandal and Maguire actually ended up facing a lawsuit because of it.
Famous blackjack buddies
We’ve all seen the hilarious Matt Damon vs Ben Affleck debate, not only on Jimmy Fallon, but on various shows and sites. Regardless, the two are quite good mates and even went to Vegas together to make some bets on the blackjack tables. Now while it wasn’t against each other, the two played together instead, which was a lucky choice since they ended up winning $800,000 from three $20,000 hands.
Steven Spielberg vs George Lucas
So this one isn’t necessarily about bets on casino games, but it’s interesting. In 1997, Steven Spielberg made a bet with fellow director and friend, George Lucas, that has cost Lucas $40,00,000 and counting. Lucas visited Spielberg on his set of Close Encounters just before Star Wars: A New Hope was released. Both argued that each other’s film would do better than their own. Therefore, the only obvious choice was to make a bet against one another. Whichever movie was the most successful would see the director giving the other director 2.5% of the stakes.
Star Wars made $755 million in 1977, and to this day Lucas is the one paying for it. Though Lucas did end up selling Star Wars to Disney for $4 billion, so he definitely isn’t out of pocket.
The boxing bets
While this isn’t a bet against friends, it is a bet on them. Curtis “50 Cent” Jackson, has been friends with boxer Floyd Mayweather for quite some time, even citing that he sees him as a brother. So when the fight between Mayweather and Manny Pacquiao was planned, 50 Cent placed a whopping $1.6 million bet on Mayweather to beat Pacquiao. The friendship paid off with Mayweather beating Pacquiao unanimously on May 2, 2015.
P. Diddy vs Mark Wahlberg
On the same fight, long-time friends Sean ‘Diddy’ Combs and Mark Wahlberg bet $250,000 against each other over the result. P-Diddy won the bet when Mayweather won the fight, with Wahlberg’s wife taking to Twitter to let out her disbelief in the win.
Kanye vs 50 Cent
Not quite a casino style bet, nor a sporting wager, but a gambling bet nonetheless. 50 Cent bet Kanye that his album (released September 11, 2007) would do better than Kanye’s album released on the same day. If it didn’t and Kayne’s did better in terms of how many records were sold, then 50 Cent would no longer bring out solo albums.
It definitely isn’t obvious who won the bet due to the regular release of solo albums from the two artists, but Kanye did in fact beat 50 Cent in terms of the number of records sold on September 11. 50 Cent did not stick to his word and continued to release solo albums, later claiming the bet was just to bring more hype to the release of both of their albums.
Leonardo DiCaprio vs. Toby Maguire
While the two are regulars in the poker rings, this hasn’t stopped the pair from making an interesting side bet. DiCaprio and Maguire bet $25,000 that the other would be a dad first. DiCaprio is still sans child but he is up 25 grand since Maguire’s daughter Ruby Sweetheart was born November 7, 2010. We wouldn’t recommend Ruby try her luck on the tables when she grows up.
George Clooney vs. Nicole Kidman and Michelle Pfeiffer
George Clooney had a rough divorce, so much so he was willing to place a serious wager on never marrying again. He bet both Nicole Kidman and Michelle Pfeiffer 10 grand each that he would still be single at the age of 40. He won the two wagers but returned the winnings to make a double-or-nothing wager against the two, stating he would still be unmarried at 50. He won again, but we hope the two women accepted a triple-or-nothing wager for him being single at 60, because they’d win.
Is betting against your friends a good idea?
There are advantages and disadvantages when it comes to gambling against your friends. If you’re both good for the money and are quite aware of each other’s financial situation in terms of it being stable, then there shouldn’t be any dramas. However, if you know they have been notorious for not paying, are actually in a bad place financially, or they know how to guilt trip you if they do lose, it is definitely a bad idea to place a wager between friends. It can be quite fun when betting with friends, but it can easily turn sour.
Removing the middleman when gambling
A major advantage for betting between friends is that it removes the need for the middleman. Just say you and your friends are having a cheeky bet on the outcome of a sports game, there is no need to use a bookie and therefore you won’t be paying a fee to them, which is sometimes referred to as the Vig or Vigorish.
There can be many bets made between friends, but whether its over a game of blackjack, poker, craps, a sports match outcome, or something silly such as who will be married first, always remember to keep it friendly.