Hip hop and gambling go way back – especially when rappers talk about money. Traditionally, these gambling references revolved around the glitz of physical casinos. But recently, things have changed.
Drake turned heads in the online gambling world when he partnered with a cryptocurrency casino. Not only did he become its face – but his massive bets also got everyone talking.
There was even a viral video of him teaching Lil Yachty how to play roulette. It is clear – modern hip hop is embracing the convenience of online gambling in ways older tracks couldn’t.
Let’s get into some iconic rap songs about gambling.
Vegas by Kendrick Lamar
This track’s title says it all.
Kendrick captures the thrill of Sin City – referencing blackjack, craps, and poker. The song didn’t make it onto his album To Pimp A Butterfly, but it is still a gem.
He even uses “Vegas” as a metaphor for taking risks on someone worth betting on. The verses, “Doin’ blackjack, twenty-one, twenty thousand in it. Probably twenty more before I’m done,” paint a vivid picture of high-stakes blackjack.
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It Was a Good Day by Ice Cube
“It Was a Good Day” Ice Cube’s iconic is about an ideal day where everything just clicks.
Among other wins – he raps about an incredible streak at the craps table: “What’s the haps on the craps?
Cube’s lucky rolls of sevens and elevens highlight his perfect day. For those unfamiliar – craps is a dice game where those rolls are major wins.
All In – Lil Wayne
Lil Wayne’s “All In” is probably one of the most obvious nods to gambling.
I mean, the title says it all.
Going “all in” is about putting everything on the line, right?
In the song – he is not just talking about poker or chips. It is about life. Love. Hustle. The stakes are always high – and Wayne’s approach is fearless. Honestly, I think it is a great reminder to be bold when it matters most.
Pokerface by Ghostface Killah
Ghostface Killah of Wu-Tang Clan fame dropped “Pokerface” in his 2006 album More Fish. Featuring Shawn Wigs – the song dives deep into poker culture – with nods to the World Series of Poker and the movie Rounders.
One standout line, “Can’t lose what you don’t push into the pot,” ties life and poker together – risks are necessary for rewards. Released during the height of the poker boom – the song captures the essence of Texas Hold’em and its high-stakes drama.
If you are a poker fan – this track’s rich terminology and bold vibe will resonate.
The Gambler – Kenny Rogers (Hip Hop Remix)
All right, this one is technically a country song.
But hear me out.
The hip hop remixes of “The Gambler” have brought it straight into the genre’s world. The message—”Know when to hold ’em, know when to fold ’em”—resonates in so many ways. Life is all about timing, right?
Whether you are at the poker table or making a big life decision – it is the same deal. I have heard versions of this song sampled in tracks that make you feel like you are right there – making high-stakes bets.
Who Gon Stop Me by Jay-Z and Kanye West
From their collaborative album Watch the Throne – Jay-Z and Kanye West’s “Who Gon Stop Me” celebrates their luxurious lifestyles and love for gambling.
Jay-Z drops the line, “I’m at the table, I’m gamblin’ Lucky lefty, I expect a seven,” referencing craps and his old nickname, “Lucky Lefty.”
The track oozes confidence – fitting for two rap giants who know the stakes and always play to win.
Jackpot – The Sugarhill Gang
Here is a classic.
The Sugarhill Gang was one of the first to bring gambling into hip hop. In “Jackpot,” they talk about hitting it big – whether it is money, luck, or just life in general.
The upbeat rhythm makes it feel less about the risk and more about the reward. Listening to this one always makes me think about how exciting it must feel to strike gold—metaphorically or literally.
As times change – we are seeing hip hop grow with modern trends like online gambling. Drake’s involvement is just the beginning—there is no doubt we’ll hear even more references to online casinos and crypto gambling in future tracks.
Hip-hop and gambling—whether at the table or on your phone—remain a perfect match.
