High-Rolling Hip Hop Stars

Date Created: Aug 01
Written by Jerico

Gambling is an activity that people from all walks of life particularly enjoy. Whether it’s the mailman or the CEO of a Fortune 500 company, gambling is a popular past time amongst everyone. Rappers and hip-hop stars are no different!

To use a popular word in the hip-hop lingo, these musicians and artists like to “floss,” what with their massive mansions, expensive and fancy automobiles, iced out jewelry and wardrobes packed with designer couture. The hip-hop world is often associated with excess, gaudiness, and materialism, which is ironic since one thing that these wealthy rappers want more of is money.

If hip-hop culture is themed on bling, and rappers often say money doesn’t mean a thing, shouldn’t hip-hop and gambling complement each other? Casino games and hip-hop music go well together like a fine-tuned melody. Thanks to this harmonious relationship between the two industries, it’s hardly surprising that many of the world’s top hip-hop artists have tried their hand at casino games.

Whether it’s a stint at the blackjack table or a round of poker, those with a knack for notes also seem to have a way — or not — with gambling. So, in an effort to highlight the harmony between casino gaming and hip-hop culture, we’ve picked out some of the biggest names in hip-hop that have hit the high notes in the betting world!

1) Nelly

Instantaneously recognizable by the ominous plaster on his cheek, the St. Louis-born and bred rapper named Cornell Iral Haynes, Jr. — better known as Nelly — kicked off his successful solo hip-hop career in 2000 with the smash hit album, “Country Grammar.”

His third single, “Ride Wit Me,” was a global hit that reached the top ten in many countries all around the world, instantly making him a worldwide phenomenon. He followed that up with another gold-selling record called “Nellyville,” which included the tracks “Hot in Here” and “Dilemma” featuring former Destiny’s Child member, Kelly Rowland — songs that still regularly make playlists today.

When away from the nightclubs and massive crowds that followed him wherever he went, Nelly also started the non-profit organization called “4Sho4Kids” and is the owner of an energy drink called Pimp Juice, which shares its name with one of his songs.

Another passion he has is for the game of poker. Just how much does he love it? He went as far as playing in the prestigious 2007 World Series of Poker Main Event. He was also a regular on the PokerStars European Poker Tour circuit. However, as much as he loves poker, it appears that the game has not reciprocated the same admiration as Nelly has taken out far less than he has put in over the years, cashing out a mere $5,153 so far.

2) Gladys Knight

Known as the “Empress of Soul,” Gladys Maria Knight is an American singer, songwriter, actress, businesswoman, and author. A seven-time Grammy Award-winner, Knight is known for the hits she recorded during the 1960s, 1970s, and 1980s with her group Gladys Knight and the Pips, which also included her brother Merald "Bubba" Knight and cousins Edward Patten and William Guest.

Gladys Knight wrote in her autobiography that she considered herself to be suffering from a gambling addiction with baccarat and sports betting. In the book, “Between Each Line of Pain and Glory: My Life Story”, Gladys wrote about her decade-long struggle in which she won less than she bet.

While she also enjoyed sports betting, it was her addiction to Baccarat that would cost her tens of thousands of dollars in just one table sitting. In the late 1980s, Knight finally admitted she needed help and turned to Gamblers Anonymous after a high-stakes binge that cost her $45,000. The singer of “Midnight Train to Georgia” and “Heard it Through the Grapevine” also admitted in the same book that she cared little for the money she lost but looked for help she desperately needed because she was gambling rather than taking care of her son.

3) Jay Z

Considered to be the pre-eminent titan in the industry, Jay Z — whose real name is Shawn Carter — is an American rapper, songwriter, producer, entrepreneur, and record executive. Considered among the best rappers of all time, he is regarded as one of the world's most significant cultural icons and has been a global figure in popular culture for over two decades.

Outside of his musical career, Jay-Z has also attained significant success and media attention for his career as a businessman. In 1999, he founded the clothing retailer Rocawear, and in 2003, he founded the luxury sports bar chain 40/40 Club. Both businesses have grown to become multi-million dollar corporations and allowed Jay-Z to fund the start-up for the entertainment company Roc Nation, which was founded in 2008. In 2015, he acquired the tech company Aspiro, and took charge of their media streaming service Tidal, which has since become the world's third-largest online streaming company. His marriage to one of the most famous musicians in the world, Beyoncé, has also been a source of immense media attention.

However, where he is not as good is in the casino, which also happens to be a favorite place of his. While there is no doubt that he can afford the odd bad beat but, as a bit of a fish when it comes to blackjack and poker, he is another who has probably lost count of how much he has lost at the high-stakes tables he regularly frequents. It has been claimed that, on a trip to Las Vegas, he lost $500,000 in a single high-stakes poker hand, which he probably barely even noticed.

Jay-Z has also admitted that he enjoys the gambling scene when he is visiting London. In an interview with the publication Time Out, Jay Z mentioned that he was quite proud of his blackjack and poker skills.

"I'm a pretty big, almost professional, gambler," he was quoted as saying. However, the 38-year-old refused to name his preferred casinos for fear of being hassled at the tables.

He added: "I'm not gonna say any names because that'll mess it all up, but there are these little private clubs you can go to in the West End where you can hang out and gamble, and it's pretty cool."

4) 50 Cent

Curtis James Jackson III or more known as the superstar artist 50 Cent, is an American rapper, singer, songwriter, actor, television producer, entrepreneur, and investor. In his career, 50 Cent has sold more than 30 million albums all over the world and has won several awards, including a Grammy Award, thirteen Billboard Music Awards, six World Music Awards, three American Music Awards, and four BET Awards.

50 Cent has been known to enjoy an ill-advised gamble, especially given that he never stakes as little as his namesake, $0.50, on a bet. No, 50 Cent prefers to go all in at way higher, once even famously betting as much as $1 million on his friend at the time, Floyd Mayweather Jr, when he took on Oscar de le Hoya in Vegas a few years back.

Also, in 2012, he placed a winning bet of $500,000 on the New York Giants against the 49ers in the NFC Championship. Despite, doing well on some bets, he once penned the following unintelligible lyrics for a track that was released back in 2007 called “What You Got.”

“I got a gambling problem. I bet you **** I’mma be back bustin’. But you won’t notice me when that gat dumpin’, you wan’ bet?. I lost money when I bet on Roy. Won money when I bet on Floyd, I’m the one that bet on boy,” and, true to form, 50 Cent has previously filed for bankruptcy despite earning millions.

5) Birdman

Bryan Christopher Williams, known by his stage name Birdman, is an American rapper, record executive and entrepreneur. He founded the recording company Cash Money Records with his older brother Ronald "Slim" Williams in 1992.

Birdman is well known for being a shrewd businessman and is also heavily invested in a clothing line as well as an oil and gas company. However, Birdman enjoys spending some of his disposable income on sports betting and at the casino. In 2011, he lost $2 million wagering that the Miami Heat would win the NBA Championship ahead of the Dallas Mavericks.

It’s not all bad luck, though. In Super Bowl XLV, he won $1 million for backing the Green Bay Packers.

6) P Diddy

Sean John Combs, who is more popularly known by the stage names Puff Daddy, P. Diddy, Puffy or Diddy, is an American rapper, singer, songwriter, record producer, record executive, actor, and entrepreneur. He is widely considered to be a legend in the rapping and hip-hop business.

When it comes to living the highlife and basking in luxury, Diddy is peerless. He fast became known as the king of bling and it’s no surprise that he has a penchant for gambling and casinos too. When Diddy is in Las Vegas, you can be sure to find him at the high stakes tables playing his favorite game of blackjack.

It is totally unsurprising to see that back in 2012, when Harrahs’ Atlantic City launched their new selection of poolside blackjack tables, Diddy was asked to perform at the opening ceremony. The rapper not performed but he did the same on the blackjack tables, trying first-hand the new products. In fact, he was asked to place the first wager on the new luxurious selection of blackjack tables in Atlantic City.

7) Young Thug

Jeffery Lamar Williams, known professionally as Young Thug, is an American rapper, singer, songwriter, and record producer. Known for his eccentric vocal style and fashion, he first received attention for his collaborations with rappers Rich Homie Quan, Future, Birdman, Cash Out, Shawty Lo, and Gucci Mane.

Young Thug is widely regarded as one of the best rap acts to come up over the last few years, but close associates say that his one true passion is actually gambling. He is usually regarded as an avid gambler, and his team actually indicate that they have to keep an eye on him and deter him when he seems to be spending too much time at the tables. A story that was published in XXL told about how Thug was cleaned out of tens of stacks but fought back to gain back all his cash and then won a $100,000 watch right after that.

Thug’s favorite game is dice, and he likes going at it with his boys. A sad twist to the story is that the rapper’s brother died as a result of a gambling argument. It is also reported that Thug is so smooth and skillful with his table game that other gamblers refer to him as “Slime.”

8) Drake

Aubrey Drake Graham is a Canadian rapper, singer, songwriter, record producer, actor, and entrepreneur. As an entrepreneur, Drake founded the OVO Sound record label with longtime collaborator 40.

Drake has also gained a reputation for being a notorious gambler. According to a report on PageSix, Drake blew some big bucks during a trip to Hard Rock Hotel & Casino in Atlantic City. The rapper arrived an hour late, closer to 3 a.m., to DAER Nightclub for a club performance that was scheduled for 2 a.m. after his Philadelphia stop on the "Aubrey & The Three Migos" tour with Migos.

Sources said that Drake and his clique were heading to the strip club, Scores, inside of Hard Rock before changing their mind because it was packed. DJ Spade, Drake's affiliate, was reportedly spinning inside of the strip club. According to the report, “Drake took one look and decided to go gambling,” before adding that, "He got the itch."

It was also reported that Drake "stayed at the table” for the evening and the rapper lost nearly $200K gambling that evening. However, Drake likely still had some dough left from his appearance earlier in the night. Drake and his crew also had the casino opening up their restaurant Sugar Factory after it closed.