Drake rang in his 40th birthday with more than 400 guests, million-dollar prizes and a surprise performance from the Backstreet Boys — one day after adding another record to his already historic résumé.

The Toronto superstar celebrated at New York’s Casa Cipriani on Friday night (Oct. 23), hours before officially turning 40 on Oct. 24. According to TMZ, guests were treated to luxury giveaways including Chanel and Hermès handbags, while a game show held during the party offered cash prizes ranging from tens of thousands of dollars up to $1 million.

The night’s biggest musical surprise came courtesy of the Backstreet Boys, who performed for the crowd before Drake joined them onstage for their 1999 hit “I Want It That Way.”

Amid the spectacle, Drake took a moment to reflect on the milestone.

“Tonight isn’t about a tour, an album release, or a bunch of videos we shot,” he told the room. “It’s about being alive, staying alive.”

The New York celebration capped several days of birthday 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. Popcaan was among those in attendance.

Drake later 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 (Oct. 22).

The Backstreet Boys appearance also carried some history. In July 2022, the group brought Drake onstage during their DNA World Tour stop at Toronto’s Budweiser Stage and introduced him as their “sixth member” before performing “I Want It That Way.”

Drake told the crowd that night that the song had soundtracked a formative memory at his bar mitzvah, when a girl he liked approached him and 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 recalled, before calling the track “one of the greatest songs of all time.” He joined the group for the performance, even weaving portions of his own “Hold On, We’re Going Home” into the Backstreet Boys classic. Four years later, the song returned as the soundtrack to another milestone.

Drake’s 40th birthday arrived alongside another major career milestone. On Friday (Oct. 23), the Recording Industry Association of America awarded him 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. Drake now holds 18 Diamond plaques, extending his record for the most of any artist.