With all the other news that tends to swirl around them, the fact that many of the best-known rappers also happen to be avid gamblers is not exactly common knowledge. Yet this is evident in the music videos and lyrics that show them living the high life, spending money on mansions, women, and cars—as well as gambling and placing wagers on their favorite games.
Because of their love of gambling and cash, many hip-hop artists wager big chunks of change during games with their homies, visiting high-profile casinos, and playing on online casinos. Below are some of the most famous rappers and their infamous wagers.
1. Sean Combs (P. Diddy)
Best known for his hit song “I’ll Be Missing You,” P. Diddy is one of the most recognized names in hip-hop. With his wide range of efforts earning him a net worth of around $740 million, it is no wonder he likes to gamble.
The rapper and businessman is most fond of blackjack and is known to feed his hobby at physical tables and online. He also likes to wager on sporting events — his most notable wager involved actor Mark Wahlberg in a bet worth $250,000 in favor of Floyd Mayweather Jr. in his final fight of many against Manny Pacquiao.
This massive bet on a single fight paid off for the rapper when Mayweather won the match — proving that P. Diddy’s big risks sometimes come with even bigger rewards.
2. Shawn Carter (Jay Z)
Jay Z is widely known in the industry, having released over 13 studio albums and amassing a net worth of about $1.3 billion.
The popular rapper is said to favor blackjack and poker above any other games. He also has a reputation for only playing at high-stakes tables where the chance to lose (or win) big is greater.
In 2015, the rapper lost an undisclosed six-figure amount when betting on a boxing match against Oscar De La Hoya. In addition, it has been said that he lost almost $500,000 in a single hand of Texas Hold ‘em in Las Vegas. Luckily, he has the net worth to afford these losses.
3. Curtis Jackson (50 Cent)
“In da Club” is easily one of the most popular and recognizable songs within the hip-hop genre. The iconic tune, sung by 50 Cent, aided greatly in gaining the rapper a net worth of $52 million. While significantly less than others, this is still no small amount.
The rapper’s lower net worth may be because of the insane wagers he has been known to make. Although he loves table games like blackjack and has dabbled in slots like those found on slotsource.com, most of Jackson’s wagers have focused on boxing and other sporting events. Most notably, he wagered around $1.6 million for Floyd Mayweather to win his fight against Manny Pacquiao in 2015.
Aside from this, he has previously bet almost $1 million on a fight between Floyd Mayweather and Oscar De La Hoya and a further $500,000 on an NFC Championship between the New York Giants and San Francisco 49ers.
4. Cornell Haynes III (Nelly)
Nelly, best known for his number one hit “Dilemma,” has released 15 studio albums over his long-spanning career. This has led him to be one of the most prominent rappers in the industry, with a net worth of $45 million.
This popular rapper is known for his love of Texas Hold ‘em. However, his participation in the 2007 World Series of Poker pushed his love of gambling into the spotlight. In addition to this, he often plays in the PokerStars European Casino Poker tournaments.
While there is hardly any news on whether Nelly has any luck at gambling, the consensus is that the rapper often loses way more than he wins. And considering his total online poker tournament payouts have only totaled a measly $5,135, that truly seems to be the case.
5. Jeffery Atkins (Ja Rule)
Known for many great tunes, including “New York” featuring Fat Joe and Jadakiss, Ja Rule has a net worth of $4 million. Considering he has released seven studio albums, this rapper is worth substantially less than many others on this list.
However, his slightly lower net worth may result from his love of poker. This love has extended so far that Ja Rule launched his own online poker room. Sadly, the room didn’t last long before it was shut down.
While there is no record of how much this rapper has won (or lost), he is known to frequently host poker parties at his home.
6. Aubrey Graham (Drake)
Drake, who released his seventh studio album in June 2022, is well-known for his song “One Dance,” alongside many others. This song became a number-one hit in 15 different countries, making him a popular name in the hip-hop industry and helping him amass a net worth of $260 million.
While the rapper tries incredibly hard to keep his private life out of the public eye, he has been known to enjoy gambling during his downtime. The most notable instance of his gambling losses was the $200,000 he lost in a single card game.
Drake has recently partnered with an online casino and sportsbook website to promote various events. This partnership even led to the famous rapper giving away 35 bitcoins to fans and players during a live Twitch stream. On the same night, he won $18 million playing roulette, but unfortunately, he soon lost this and even more.
Rappers work in a massive industry but have a knack for enjoying their time off by playing within another hugely popular industry — gambling. As seen above, some of the biggest names in hip hop love gambling and have even (at times) been very successful at it.