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Inside Drake’s over-the-top 40th birthday bash featuring $1M cash prize, Chanel bags and Backstreet Boys

October 24, 2026
in News
Inside Drake’s over-the-top 40th birthday bash featuring $1M cash prize, Chanel bags and Backstreet Boys

You only turn 40 once…

Drake reportedly went all out for his milestone birthday, treating guests to Chanel bags, a $1 million cash prize and a surprise performance by none other than the Backstreet Boys.

The rapper hosted the blowout bash at the exclusive Casa Cipriani hotel in New York City on Friday, inviting more than 400 friends and family members, according to TMZ.

Drake arrives at Cipriani wearing a sparkling black tuxedo jacket and bow tie.
Drake reportedly went all out for the milestone birthday, treating guests to Chanel bags, a $1 million cash prize and a surprise appearance by none other than the Backstreet Boys. (The rapper is pictured above arriving at the party Friday night.) Dario Alequin / BACKGRID
Drake surrounded by people in New York City.
Drake hosted the blowout bash at the exclusive Casa Cipriani hotel in New York City on Friday, inviting more than 400 friends and family members. UrbanxDivinity / BACKGRID

The outlet also reported that the iconic ’90s boy band — made up of Nick Carter, Howie Dorough, AJ McLean, Brian Littrell and Kevin Richardson — kept the party going with a nostalgic performance.

The “One Dance” hitmaker is said to have “spared no expense,” treating partygoers to lavish giveaways, including designer handbags from luxury brands like Chanel and Hermés.

He also reportedly turned the shindig into a game show, giving lucky guests the chance to win cash prizes ranging from tens of thousands of dollars to as much as $1 million, per TMZ.

He was dressed for the occasion, photographed arriving at the party in a tuxedo with a shimmering jacket.

Members of the Backstreet Boys, including Howie Dorough, Kevin Richardson, Nick Carter, AJ McLean and Brian Littrell, pose together at a movie premiere.
TMZ reported that the Backstreet Boys, made up of Nick Carter, Howie Dorough, AJ McLean, Brian Littrell and Kevin Richardson (seen above at the Los Angeles premiere of “Paw Patrol: The Dino Movie”) kept the party going with a nostalgic performance. Getty Images for Paramount Pictures
Nick Carter attending Drake’s birthday party in New York City.
After the iconic ’90s pop boy band entertained guests, Drake reportedly treated partygoers to lavish giveaways, including designer handbags from luxury brands like Chanel and Hermés. (Nick Carter of the Backstreet Boys is pictured above arriving at Drake’s party.) UrbanxDivinity / BACKGRID
Drake wearing a black sequined tuxedo and bow tie, flanked by bodyguards in New York City.
Drake (seen above arriving at the party in a tuxedo with a shimmering jacket) also reportedly turned the shindig into a game show, giving lucky guests the chance to win cash prizes ranging from tens of thousands of dollars to as much as $1 million GC Images

Drake, born Aubrey Graham, is no stranger to the luxury lifestyle.

In August, the “God’s Plan” singer showed off his one-of-a-kind, diamond-encrusted Rolex Daytona on Instagram, calling the iced-out timepiece “the most important thing I have ever had the pleasure of owning.”

The custom design was created to celebrate the “the record breaking milestones of 2026,” Drake wrote in the caption, seemingly referencing his trio of album releases this year, including “Iceman.”

He even had the words “Freeze the World,” a lyric from his song “Make Them Know” off “Iceman,” engraved on the back of the watch in blue lettering — with the bespoke Rolex estimated to be worth as much as $5 million.

Drake smiling and clapping while attending a Toronto Raptors basketball game.
Drake (pictured above at a Toronto Raptors game in 2024) is no stranger to the luxury lifestyle, having recently shown off his one-of-a-kind, diamond-encrusted Rolex Daytona. Getty Images
Drake attends the UK Premiere of
Drake (seen above at the UK premiere of “Top Boy”) gave fans a glimpse inside his $185 million private jet after it received a series of upgrades last year. Dave Benett/WireImage

“Please do not get your local jeweler to recreate,” Drake urged his followers, adding, “This is a standalone and a part of history.”

Last year, the OVO founder gave fans a glimpse inside his $185 million private jet after it received a series of upgrades.

He showcased his Boeing 767 on Instagram in July 2025, revealing a bedroom complete with a king-size bed, a flatscreen TV and mirrored walls.

Drake also flaunted the main lounge, which featured faux-fur seats adorned with custom pillows and a gambling table, alongside a movie screening area and three additional bedrooms for guests looking to “duck off.”

The post Inside Drake’s over-the-top 40th birthday bash featuring $1M cash prize, Chanel bags and Backstreet Boys appeared first on Page Six.

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