Gambling and hip hop have always had this cool relationship—especially when you look at some of the biggest names in the industry.
Yes, rappers are known for blowing their millions on flashy cars, custom designer outfits, and even crazy stunts (like Lil Uzi Vert getting a diamond literally implanted in his forehead).
But something they love just as much? Gambling at casinos.
Let’s break down how some of these hip hop stars take their love for risks from the studio to the betting table.
50 Cent
First up, you already know we have to talk about 50 Cent. The guy’s name alone screams bold moves – and it is no different when it comes to gambling at casinos.
He has dropped some wild bets over the years. Back in 2012 – 50 bet a casual half a million dollars that the New York Giants would make it to the Super Bowl. Spoiler alert – they did. But he didn’t stop there—he doubled down – betting on the Giants to win the game, and guess what? He cashed in.
Fast forward a few years – and 50’s making headlines again – this time with a $1.6 million bet on Floyd Mayweather to beat Manny Pacquiao. Floyd won, of course – and 50 walked away with a sweet $2.3 million.
Oh, and let’s not forget his more petty side—like when he publicly bet $750,000 that Mayweather couldn’t read a single page of a Harry Potter book. (Yes, that one never actually happened – but it is still classic 50 drama.)
Nelly
Nelly is a big poker guy and has played in some high-stakes games – including a Rolling Stone 40th-anniversary tournament where he took the prize and donated the winnings to charity.
He has also competed multiple times at the World Series of Poker. While his total winnings—around $100K—don’t sound like crazy rapper-level money – Nelly has skills at the poker table.
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Young Thug
Young Thug’s story is more of a cautionary tale. In 2021, he – admitted on social media that he lost $800,000 in one night at a Vegas casino. Ouch. And if that was not enough – he tried to win it back. He managed to recover $100,000 and then lost that, too.
Fans joked online about helping him “get revenge” on the casino – but let’s be real – gambling can be brutal. That’s why it is best to choose a trusted platform and play with caution. These days, though – Thug has got way bigger things to worry about – like his legal troubles.
Jay-Z
Jay-Z gambling? He does it a bit differently – with strategy + style. Sure, he has played his fair share of poker – but his most iconic gambling move was not even at a table.
In 2021, Jay partnered with Caesars Entertainment to pitch a casino idea for Times Square. It was not about the money, either—Jay wanted the casino to benefit the city and create opportunities for Broadway workers and local businesses.
Even though the bid didn’t go through – it helped bring attention to the legalization of sports betting and casinos in New York. Leave it to Jay-Z to turn gambling into a business opportunity.
Drake
Drake basically turned gambling into a public spectacle. He has been live-streaming his roulette sessions and even posting massive sports bets online. This shows that Drake isn’t shy about showing off his love for high-stakes gambling.
There is even a running joke about the “Drake curse,” – where teams or athletes he bets on seem to lose. But that hasn’t stopped him from scoring big wins.
One of his most insane victories came at a roulette table – where he reportedly walked away with a jaw-dropping $17 million in a single night. For Drake, gambling is just another way to add some drama and excitement to his already over-the-top lifestyle.
Birdman
Birdman, Cash Money Records co-founder and all-around high-stakes kind of guy – is no stranger to throwing around massive bets. Back in 2012 – 50 Cent claimed Birdman bet $5 million on the Super Bowl – though that’s never been officially confirmed.
What is confirmed is Birdman’s love for big sports bets. He reportedly bet $2 million on the Miami Heat to win the 2011 NBA Finals (and won) and took home $1 million after betting on the Green Bay Packers to win the Super Bowl. With a net worth of around $160 million – Birdman’s gambling habits fit right in with his fearless persona.
So yes, these are some of the top hip hop artists that are into online casinos and gambling.
