One moment at a glitzy party revealed exactly where Michael Jordan draws the line with rap. Yep, when Michael Jordan made a blunt gesture at a flashy Def Jam party, it didn’t just ruffle a few feathers—it sparked serious buzz across the $15.7 billion hip-hop scene. But what truly caught everyone’s attention wasn’t just his icy brush-off of the genre—it was the two names he didn’t dismiss: Jay Z and Drake. For someone who has long had a love-hate relationship with rap, Jordan’s choice to make exceptions speaks volumes. Now here’s where things get interesting.

Despite being a legend constantly name-dropped in hip-hop lyrics and idolized in rap circles, Michael Jordan has never fully embraced the genre. Back in the late ’90s, even when rap royalty tried to connect with him at events, he reportedly gave them the cold shoulder. All the while, his Air Jordans became fashion staples in hip-hop culture. Confusing, right? But it starts to make sense when you realize that His Airness has always leaned into a different musical lane.

Mike has openly said he prefers jazz and soul—think Anita Baker, James Brown, Diana Ross. In an interview with ABC, he flat-out admitted he didn’t listen to Public Enemy or other rap groups, even though they helped hype up his brand. A defining moment in this saga came during the aforementioned Def Jam holiday party. According to N.O.R.E., Jordan was told that Method Man and Redman wanted to meet him. His reply? A sharp “f— rap” paired with a wave of the hand, as per N.O.R.E. This reminder of the interesting events comes in a post on Instagram by raps.

The post further mentions that Michael Jordan brushed past every rapper, except Jay-Z. And more surprisingly, he’s gone on record saying he listens to Drake. That kind of approval doesn’t come easily from MJ. But there’s seemingly a reason these two were spared. His history with Jay Z isn’t just surface-level. The two have shared a mutual respect for years. Jordan even introduced Jay to his inner circle. Jay himself once called a dinner with MJ an “absolute dream conversation” in his autobiography. As for Drake? That connection runs deeper than music. It’s built on mutual interests, especially gambling.

Drake once called Jordan the “gambling GOAT” and even recalled intense ping-pong battles and life advice from the NBA icon. However, Mike raised some eyebrows when he was seen grooving to Kendrick Lamar’s Not Like Us. But given Drake’s account for his experiences with MJ, chances are the Chicago Bulls legend had no clue about the beef around it between Lamar and Drake.

Drake’s revelation of great moments with Michael Jordan

When two icons cross paths, stories are bound to follow—and Drake, never one to hold back on a good tale, let fans in on a few unforgettable moments he’s shared with none other than Michael Jordan. Sitting down for the House Money series, the Toronto-born rapper opened up about his most memorable gambling encounter, and who he believes sits on the throne when it comes to high-stakes risk-taking.

“Controversial take, but probably Michael Jordan. He’ll gamble on anything,” Drake said with a grin, the kind that hinted there was a lot more to the story. That knowing laugh? It was a preview of the gem he was about to drop. As it turns out, one of their most competitive moments didn’t come courtside—it came over a ping-pong table.

“I think I remember it was All-Star Weekend in Toronto, and he had an event to be at. I beat him at ping-pong a couple times, and he just wouldn’t leave the ping-pong table,” Drake recalled, still clearly entertained by the memory. “Just kept betting because he just couldn’t stomach the loss… He’s definitely not a quitter. I respect him deeply for his gambling nature.” But MJ’s connection to Drake doesn’t stop with playful wagers.

Back in 2016, just before Drake coached Team Canada in the NBA Celebrity All-Star Game, he got some serious words of wisdom from the legend himself. “Michael Jordan talked to me earlier today,” Drake told The Canadian Press after his team’s 74-64 win over Team USA at Ricoh Coliseum. “He told me to go out there, told me what plays to avoid running, told me: ‘If you want the champagne and cigars, you gotta win.'”

Their connection—marked by competition, mentorship, and mutual respect—has fans reflecting on just how deep-rooted and unique this bond is. No wonder he’s among the handful of artists, along with Jay-Z, to whom Michael Jordan listens to the rap genre.