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It’s not a secret that Michael Jordan is an avid gambler, even if there’s been a scarcity of detailed stories revealed. But Drake unveiled a battle that he had with the NBA legend in an interview for Stake, the online casino and sports betting company. Drake has a longstanding endorsement deal with Stake. The Honestly, Nevermind artist shared how he wound up in a tight battle over ping-pong with Jordan in the video, which was posted via Instagram last Thursday (March 20).
“He’ll gamble on anything. I think it was All-Star Weekend in Toronto and he had an event to be at, and I beat him at ping pong a couple of times,” he recalled. Drake referred to the former Chicago Bulls guard as his “gambling G.O.A.T.” before adding: “He just wouldn’t leave the ping pong table. He just kept betting bands. Like, 10 bands, 20 bands. He kept betting ’cause he just couldn’t stomach the loss. He’s definitely not a quitter. I respect him deeply for his gambling nature.”
The interview initially began with Drake being asked about the biggest win he ever had in gambling. The first question simply asked the Canadian superstar what his biggest win was. “Fuck… tax questions,” he responded while laughing. “The biggest win I ever had, I was actually in Dave & Busters — and this is [a] testament to playing in a brick-and-mortar casino versus playing on Stake. I was getting this random girl to call roulette numbers and I hit, like, eight out of 10 numbers. I think by the end of the night, we had won like $38 million, $40 million. Yeah, $40 million.” Drake continued, “It was crazy. The craziest night ever gambling, for sure. January of 2024 was crazy. There’s not even a word for it.”
Drake’s gambling adventures have become a much-discussed topic among Hip-Hop fans, particularly his losses. He lost $355,000 betting on Mike Tyson to beat influencer-turned-brawler Jake Paul. Paul won the fight by unanimous decision, thwarting a potential million-dollar payday. Drake also lost a reported $2 million by betting on Israel Adesanya to defeat eventual victor Alex Perreira in their UFC bout in 2022.
https://x.com/2Cool2Blog/status/1902952874604134669
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Source: Cole Burston / Getty / Drake
Drake is once again the butt of jokes on social media, and it’s not because Kendrick Lamar dropped another diss record but because his own label had bars for him.
Spotted on Variety, Universal Music Group let the chopper spray on Drizzy in a motion to dismiss the Canadian’s lawsuit against the music label accusing them of pushing Lamar’s epic diss record, “Not Like Us.”
In the dismissal, UMG claims that Drake is in his feelings and suing because he “lost a rap battle” and his decision to sue was only to “salve his wounds.”
Damn.
Per Variety:
The motion, filed earlier today and reviewed by Variety, took a cutting approach to making the case for dismissal, claiming that Drake “lost a rap battle that he provoked and in which he willingly participated. Instead of accepting the loss like the unbothered rap artist he often claims to be, he has sued his own record label in a misguided attempt to salve his wounds. Plaintiff’s Complaint is utterly without merit and should be dismissed with prejudice.”
The filing also calls the rapper who claimed to “study rap battles for a living” a hypocrite, noting that less than three years ago, he signed a public petition criticizing “the trend of prosecutors using artists’ creative expression against them” and stating their lyrics as fact. “Drake was right then and is wrong now.”
The motion continues, “Complaint’s unjustified claims against UMG are no more than Drake’s attempt to save face for his unsuccessful rap battle with Lamar.”
Drizzy’s Attorney Responds To UMG’s Filing
Drake did respond, well his attorney, Michael J. Gottlieb, did in a statement shared with Variety.
“UMG wants to pretend that this is about a rap battle in order to distract its shareholders, artists and the public from a simple truth: a greedy company is finally being held responsible for profiting from dangerous misinformation that has already resulted in multiple acts of violence. This motion is a desperate ploy by UMG to avoid accountability, but we have every confidence that this case will proceed and continue to uncover UMG’s long history of endangering, abusing and taking advantage of its artists.”
Social Media Is Clowning Drake
Drake’s attempt to sue UMG was already frowned upon by music and Hip-Hop fans alike, and now he catching more strays after getting clowned by his own label.
“UMG literally hit Drake with a Reverse uno,” one post on X, formerly Twitter, read.
Another post read, “all that talk of kendrick being a hypocrite drummed up by that fanbase only for UMG to point out how drake is also one……”
Welp.
You can see more reactions in the gallery below.
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Source: Getty Images / YesJulz / DJ Akademiks
Two of the biggest culture vultures, DJ Akademiks and YesJulz clashed over the weekend and social media was here for the drama.
Let’s make this abundantly clear while y’all are here, no likes either of these individuals, BUT, we must admit, we ain’t mad at YesJulz for stating the obvious about DJ Akademiks.
HotNewHipHop reported that everyone’s favorite dark room streamer claimed from his gaming chair that Kendrick Lamar was a creative director on Playboi Carti’s latest album, I Am Music.
“Kendrick is creative directing the whole shit,” Akademiks claimed.
Akademiks is no stranger to saying wild stuff for clicks, and that claim was quickly debunked by Carti’s longtime producer, F1LTHY, who most notably created the beat for Carti’s song “All Red.”
“Kendrick fam but he is NOT the creative director of this album,” F1LTHY said in a post on X, formerly Twitter. “This Carti album.”
You would think that would have ended the discussion, but no. Akademiks doubled-down on his claim, stating that Carti himself gave him the information, even taking a jab at the producer.
“No disrespect to F1LTHY, I don’t know who the f**k F1LTHY is,” the Drake stan said. “Kendrick is on the album. Whether it’s creative director, executive producer, I don’t give a f**k. I’m only going off what Carti told me.”
YesJulz Clowned Akademiks On X
YesJulz saw Akademik’s disrespect of F1LTHY and injected herself into the situation writing on X, “Not knowing F1LTHY is one of Carti’s main collaborators in 2025 as a journalist covering hip-hop is surely one way to admit you suck at your job.”
Akademiks caught wind of YesJulz’s response and went on a wild rant, dipping into misogynistic bag calling the influencer a “wh*re” for stating the obvious about him.
YesJulz had plenty to say in response, adding “Bro bout to pop a blood vessel” and that she doesn’t “don’t go back and forth with incels. I got somethin for that lil cootie patootie tho.”
DJ Akademiks is not having a good weekend on the socials. He is also getting clowned for sharing a video of bikini-clad women dancing on a boat to Drake’s music while talking about, you guessed it, Kendrick Lamar.
Social media has also been enjoying the back-and-forth between the two culture vultures. The gallery below shows those reactions, plus more replies from YesJulz.
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Drake is back to blazing the charts despite the overall consensus pointing to the fact that he seemingly lost the battle with Kendrick Lamar. In a new Instagram post, Drake vaguely suggests that he’s got more artistic moves on the way and teased his “next chapter.”
Taking to his preferred social media platform of Instagram, Drake captioned a series of photos with the following:
U know I grew up non confrontational and always treated this game as a sport where my pen won gold, but my these days the podium has been hard for all of us to ignore. I understand that this next chapter may leave you feeling uneasy, but I hope you see my honesty as clarity not charity that answers some questions especially about the unanswered texts you’ve been sending me.
Given that the OVO Sound honcho can be cryptic via social media, it isn’t known who this message is for or what it truly means. It could be assumed he’s ready to address all the chatter about his assumed downfall despite charting big with his latest collaborative album with PARTYNEXTDOOR, $ome $exy $ongs 4 U, which is currently the No. 2 selling album on the Billboard 200.
With the Anita Max Win tour in New Zealand and Australia put on pause, fans will certainly be awaiting new music and whatever the next moves are from Drake.
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Photo: Getty
Drake appears to be working on his next era, though he’s taken to social media to warn that it might not be for everyone.
The Canadian musician shared a post on Instagram on Monday (March 10), with its cryptic content swiftly generating much speculation as to what it might be referring to. “U know I grew up non confrontational and always treated this game as a sport where my pen won gold, but my these days the podium has been hard for all of us to ignore,” the post began.
Presumably, this could be in reference to the OVO rapper’s high-profile beef with Kendrick Lamar, which recently saw Lamar performing the incendiary “Not Like Us” at the Super Bowl LIX Halftime Show, only days after it won record and song of the year, best rap performance and song, and best music video at the Grammys.
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Drake had previously promised another round in their ongoing feud was on the horizon, with Lamar later addressing the 6 God’s claim while announcing his halftime performance. “You know there’s only one opportunity to win a championship,” Lamar said. “No round twos.”
Trending on Billboard
As Drake continues his post though, he hints that whatever comes next may be uncomfortable for some, adding that an unidentified individual has been sending him texts. “I understand that this next chapter may leave you feeling uneasy, but I hope you see my honesty as clarity not charity that answers some questions especially about the unanswered texts you’ve been sending me,” the post concludes.
The cryptic nature of Drake’s latest message is continued in the choice of photos used in the post, which – alongside selfies, live footage, and a screengrab from the 2017 film Phantom Thread – also includes an image of two Zofran pills, which the Mayo Clinic notes are “to prevent nausea and vomiting that is caused by cancer medicines (chemotherapy) or radiation therapy.”
Specifics relating to Drake’s upcoming plans remain unclear currently, but his update follows the release of his $ome $exy $ongs 4 U collaborative album with PartyNextDoor on Feb. 14, and the postponement of a number of Australian and New Zealand tour dates due to a “scheduling conflict.”
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With much of the Hip-Hop community siding with Kendrick Lamar these days and having become the butt of many jokes, Drake really seems like the definition of a lonely boy these days, and recently, a video circulating social media seems to drive home that notion, as Drizzy has taken to turning up all by himself in the club… literally.
Recently, video surfaced, which showed the Canadian crooner sitting by himself in a club that he rented out for personal use. But instead of filling it with close friends, family or women, Drizzy simply sat by himself while Sabrina Carpenter’s “Espresso” blasted out the speakers and he gambled the night away as his Stake bets played on the big screen TV’s in the club. Enjoying himself some bubbly while sitting comfortably in a fur coat, Drake seems to be at peace as he ultimately won some paper and confetti showered his person to celebrate his earnings.
We hate to say it, but it seems like the Certified Lover Boy artist needs, well, some love.
While many are suggesting that this could be Drake doing some promotion for the Stake gambling site (for which Drake has money invested in), we low-key think this is how isolated Drizzy’s been feeling as of late, as even his Nike Air Force 1s have been bricking upon release. Y’all know heads ain’t f*cking with a rapper when his/her personal Nike collaborations are dead upon arrival. Heck, even Lil Yachty’s Air Force 1s sold out when they dropped. That’s saying something.
Drake has yet to address the video of himself by his lonesome in the club, but you can bet Kung Fu Kenny is somewhere basking in his victory and in the seclusion he’s subjected Drake to in the aftermath of their classic rap battle of 2024.
Don’t feel too bad for Drake, though. The man is still richer beyond most people’s wildest dreams and has bedded some of the most famous women both in entertainment and on Instagram. So yeah, he’ll be aight.
What do y’all think about Drake politicking in the club all by himself? Is this a reflection of how he feels on the inside, or is this just promo for Stake? Let us know in the comments section below.
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Kanye West’s X, formerly Twitter, posts have been out of control for the past few weeks now, with the College Dropout artist doing everything from attacking the Jewish community (again) to proudly proclaiming himself a Nazi and a racist, but now, Ye seems to be going a different route as he’s extended an olive branch of sorts to a former rival in the King of the North, Drake.
After years of animosity between the two men, Kanye seems to have grown a soft spot for the embattled Canadian crooner/rapper as of late, and in a recent X post, Ye not only gave Drizzy a little love for his writing skills, but even went so far as to say he wants Drake to speak at his funeral.
In a random X post Kanye wrote, “I SAW A VIDEO OF DRAKE WALKING THROUGH HIS HOUSE AND SHOWING HE HAD A LIBRARY OF RYHME BOOKS MAN I WISH I COULD HAVE SEEN AND REMEMBERED THIS WHEN MY JEALOUSY OVERTOOK ME,” before adding, “I LOVE DRAKE IMA SAY THIS WHEN I DIE I NEED YOU TO SPEAK AT [MY] FUNERAL.”
The post comes after a video of Drake kicking it at an empty club all by himself while gambling began circulating social media. While some said Drizzy is showing how big ballers play out in the field, others felt this was a sign of just how lonely Drake is feeling right now, as Kendrick Lamar did to him what 50 Cent did to Ja Rule in the mid 2000s.
Obviously, these two men are going through some things right now. Given their history of beefing with each other, maybe a reconciliation would help them heal at least a small piece of themselves that they need to in order to move forward. While there’s still hope for Drake to once again be the music darling he once was at the height of his popularity, the same can’t be said for Kanye West who’s proudly stating his allegiance to the Nazi movement at a time where fascism seems to be engulfing America thanks to the Racist-in-Chief and his administration.
We can’t call it, man.
What do y’all think about Kanye West requesting that Drake speak at his funeral? Why is Kanye even thinking about his dying day? Sound off in the comments section below.
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2025 hasn’t been too kind to Drake (neither was much of 2024 thanks to Kendrick Lamar), but it seems like at least one of his legal issues is resolved; his lawsuit against iHeartMedia has apparently been settled.
According to Pitchfork, Drake and iHeartMedia have reached an agreement in the lawsuit that Drake slapped them with in which he claimed a pay-to-play plot to help boost Kedrick Lamar’s scathing diss record “Not Like Us” in 2024. With the record becoming a tremendous hit right out of the gate, rumors began to spread that the Drake was in the crosshairs of an industry wide conspiracy to take him down by helping boost spins of K. Dot’s classic diss record, to which Drake responded by suing everyone and they mama for allegedly helping the record break all kinds of records and even defamation.
Naturally, everyone accused Drake of being a sore loser and clowned him to no end, but that didn’t deter him from continuing with the lawsuits. Now, it seems like this one has come to an end, as iHeartMedia announced that “in exchange for documents that showed iHeart did nothing wrong, Drake agreed to drop his petition. No payments were made—by either one of us.”
Per Pitchfork:
Drake had accused iHeartMedia of illegally accepting the payments from Universal Music Group (UMG)—the label of both Drake and Lamar and the target of a separate Drake lawsuit—in violation of the Racketeer Influenced and Corrupt Organizations (RICO) Act. Drake’s petition, filed in Bexar County, Texas, also claimed that UMG should have blocked the release of “Not Like Us,” on the basis that it “falsely [accused] him of being a sex offender, engaging in pedophilic acts, harboring sex offenders, and committing other criminal sexual acts.” Drake is continuing to pursue his federal lawsuit against UMG, claiming the label’s release of “Not Like Us” constitutes harassment and defamation.
In the court document announcing the settlement, Drake’s attorneys said he and iHeartMedia had “reached an amicable resolution of the dispute,” according to The Associated Press.
The news comes weeks after Drake dropped his latest R&B heavy album, $ome $exy $ongs 4 U, which many fans felt was “meh.”
While we’re glad Drake and iHeartMedia were able to put this legal back-and-forth behind them, we’re just wondering if the world will ever embrace Drake like they once did, or if Kendrick Lamar ruined his reputation for all eternity going forward.
At least the man is still rich, right?
What do y’all think about Drake and iHeartMedia finally coming to terms with the pay-for-play lawsuit? Let us know in the comments section below.
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At the 2025 Oscars, Conan O’Brien dropped a witty Drake joke. This had everyone crying when the host said, “Well, we’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile”
omg this Oscars joke from Conan O’Brien
“Well, we’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile” pic.twitter.com/d7gzCFHfsF
— Spencer Althouse (@SpencerAlthouse) March 3, 2025
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The joke about Drake being a pedophile played off Kendrick Lamar’s diss track “Not Like Us.” The joke hit just after Kendrick had a massive halftime performance where he called out Drake, saying he’d probably sue if Kendrick ever performed the track. The timing of O’Brien’s joke was on point, especially with all the heat Kendrick was throwing Drake’s way. But what made it even crazier was that a producer at the Oscars was actually pushing hard for this controversial joke to air.
They believed it was going to land, no matter how risky it seemed. They were all in on the joke. Turns out, it wasn’t just O’Brien who believed in it. The punchline was written by his longtime writer, Skyler Higley, who knew exactly what he was doing.
wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. just made $50.
— Skyler Higley (@skyler_higley) March 3, 2025
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After the joke landed and the crowd reacted, Higley hopped on Twitter and let everyone know how confident he was. He tweeted, “Wrote the Kendrick Lamar joke and bet our executive producer $50 that it would kill. Just made $50.” The whole thing was a gamble, but it paid off. The producers stuck their necks out for it, and with the audience laughing, Higley cashed in. Sometimes, timing and a little bit of risk lead to a perfect moment.
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Drake and his Anita Max Win world tour in the Oceania region kicked off near the top of the month and was slated to run until March 16. However, reports have emerged that Drake will halt the remaining days of the tour due to scheduling conflicts with a promise of rescheduling those dates.
Drake was scheduled for select show stops in Australia and New Zealand after kicking off the Anita Max Win tour on Feb. 4 in Perth. As seen on Rolling Stone AU/NZ, a rep for the OVO Sound honcho confirmed that the remaining dates will be put on pause and shared a brief statement.
From Rolling Stone AU/NZ:
“Due to a scheduling conflict, four of Drake’s 16 sold-out shows in Australia and New Zealand will be postponed. We are actively working on rescheduling these dates along with adding some additional shows.
All tickets for the affected shows will remain valid for the new dates. Refunds will be available for those who prefer, but please note that as these shows are sold out, any refunded tickets will be released for sale.
We sincerely apologize for the inconvenience and appreciate your patience. Drake and the entire team have had an incredible time doing these shows and are excited to return soon.
We look forward to sharing the rescheduled dates with you as soon as possible.”
Drake was scheduled to play shows on March 4 in Brisbane, then trekking over to Sydney on March 7. The final two shows on March 15 and 16 were slated to take place in Auckland, New Zealand.
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