Talk about a milestone birthday…
Drake’s birthday celebration was nothing short of extravagant, and the rapper pulled out all the stops to mark the big 4-0. The Toronto superstar rang in his 40th with more than 400 guests, a surprise performance from the Backstreet Boys and a game show where partygoers could win up to $1 million.
According to TMZ, Drake hosted friends and family at the exclusive Casa Cipriani in New York City on Friday, October 23rd, hours before officially turning 40 on October 24. Sources told the outlet he “spared no expense,” treating guests to luxury giveaways that included designer handbags from Chanel and Hermès. The game show portion of the night reportedly gave lucky attendees a shot at cash prizes ranging from tens of thousands of dollars to a staggering $1 million. Page Six reported that Drake arrived dressed for the occasion in a tuxedo with a shimmering jacket.
The biggest musical moment of the night came courtesy of the Backstreet Boys. The iconic boy band, made up of Nick Carter, Howie Dorough, AJ McLean, Brian Littrell, and Kevin Richardson, performed for the crowd before Drake joined them onstage for their 1999 hit “I Want It That Way,” according to Billboard.
The pairing isn’t random. In July 2022, the Backstreet Boys brought Drake onstage during their DNA World Tour stop at Toronto’s Budweiser Stage and introduced him as their “sixth member” before performing the same song. Drake told the crowd that night that “I Want It That Way” was the theme song to his bar mitzvah. Subsequently, a girl he liked asked him to dance.
“That was the first time I ever felt acknowledged, and the first time I ever felt like I had a shot at being cool,” he said at the time, calling the track “one of the greatest songs of all time.” He even worked parts of his own “Hold On, We’re Going Home” into the performance. Four years later, the song became the soundtrack to another milestone.
Drake’s Birthday Brings Out Air Drake
Amid all the spectacle, Drake took a moment to get reflective. “Tonight isn’t about a tour, an album release, or a bunch of videos we shot,” he told the room, per Billboard. “It’s about being alive, staying alive.”
The New York bash capped several days of festivities that began back home in Toronto. Earlier in the week, Drake gathered with friends at the CN Tower, where he was surprised with a collage of photos and memories, and Popcaan was reportedly among those in attendance. He then traveled to New York with his mother and members of his entourage aboard Air Drake, his customized Boeing 767, and was spotted dining at SoHo restaurant Mamo on Thursday night. The plane, which Drake showed off on Instagram in 2025, reportedly features a king-size bed, mirrored walls, a main lounge with faux-fur seats and a gambling table, plus a movie screening area and additional bedrooms.
The celebration also arrived alongside a major career milestone. On Friday, the Recording Industry Association of America awarded Drake 30 new certifications, making him the first artist to surpass 350 million RIAA-certified units. Views, “In My Feelings” and “Marvin’s Room” were all newly certified Diamond, while “God’s Plan” reached 2x Diamond status. His latest album, Iceman, also went platinum just five months after its May release. With 18 Diamond plaques, Drake extended his record for the most of any artist.
Flashy moments are nothing new for him. In August, he showed off a one-of-a-kind, diamond-encrusted Rolex Daytona on Instagram that Page Six estimates could be worth as much as $5 million, with “Freeze the World,” a lyric from his Iceman song “Make Them Know,” engraved on the back. He called the piece “the most important thing I have ever had the pleasure of owning” and said it was made to celebrate “the record-breaking milestones of 2026.”
