Bets of Celebrities

Betting on the High Life: Unraveling the Extravagant Bets of Celebrities

Everybody wants to be like celebrities. However, it seems many celebrities want to become Mattress Mack and pocket millions of dollars on the bounce. Some celebrities love to flaunt their bet slips and winnings, while some have called out their own BS on over-gambling. We love it, and since they love entertaining us anyway, we’ll be here to watch it all godown. Let’s see some of these glamorous celebrity bets, their outcomes, and how much we’ll love to do so on top betting sites like

Drake ($965,000/partial win)

Riddle us this! Who loves Drake more; the fans or the gambling houses? Accurate answer: We don’t know, but it’s certainly a close call. If Drake wasn’t such a good artiste, he’d probably take up betting as a job—that’s how much he does it. The Drake’s Curse is also a thing, meaning he loses a considerable chunk of his stakes.

But at least not the whopping $965,000 he placed on Superbowl LVII in 2023. The $700,000 moneyline bet was on Kansas Chiefs v Philly’s very own Eagles, while Drake split the remaining $265,000 on prop bets here and there. Thankfully, the big-dog-bet won a $1.2 million payout, while the rest catastrophically lost. 

50 Cent ($1 million/win)

Among other things, a million-dollar bet plus another nude photo bet with a fan on Twitter has to be the biggest show of confidence in your home team. I mean, we all know the man to be bold, but this was just another level. At the XLVI Super Bowl between the New York Giants and Patriots in 2012, 50 Cent placed an enormous $1 million wager on NY. Luckily, he won the bet, walking up home with a $500,000 profit. 

Bryan “Birdman” Williams ($1 million/win)

Did you know the co-owner of Young Money Cash Money Billionaires (YMCMB) is also a big fan of doubling down on the Super Bowl? Well, you do now. He once wagered $1 million on Super Bowl XLV team, Green Bay Packers, to defeat the Pittsburgh Steelers. He doubled his bet money, getting a $2 million payout. Safe to say he won big and – as he’s fond of doing – wasted no time reminding us just how lavishly exciting he can be. First things first, he got himself a new Maybach worth 1.3 million dollars. Who knows what the other $700,000 bought for the rapper?

Floyd “Money” Mayweather ($1.1 million/win)

If you were made to guess a sure name on this list, and it wasn’t Mayweather, you definitely have some catching up to do. If his passion for boxing didn’t mean he received punches, we might have equated the same passion to betting and the bragging that comes with making a correct stake.

From college sports to the Super Bowl, the man has gathered bet slips like a collector, just like his $1.1 million wager on Oregon beating Arizona State. Was this another win? Oh yes, it was! With $1 million, he got an extra $1 million, making his payout $2 million in total. Money man does everything big, and that includes taking on college sports. 

Charles Barkley ($2.5 million/loss)

Have millions of dollars in the bank? Check! Bet millions of dollars in a casino? Multiple Check! The former basketball player and legend is known for frequenting casinos. He once admitted to losing—wait for it—a quarter of $10 million. Plainly put, the man lost a heart-rending $2.5 million on Blackjack. If you thought that was crazy, wait until you hear that six hours was all it took to lose that much.

Seems luck was absent in the casino that night. He stated, “I gamble too much.” However, he also recognised that for one who has millions in the bank, he hardly feels a thing losing that kind of money in a short spate. Again, have millions in the bank? Check!

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