Drake Surprised by Backstreet Boys at 40th Birthday Bash in New York

Drake spent the first moments of his forties with 400 friends and family members — and the Backstreet Boys.

The boy band legends were surprise performers at Casa Cipriani in New York City on Friday (October 23), and brought Drake onstage for their 1999 hit "I Want It That Way," according to Billboard.

The five-time Grammy winner previously joined BSB for a live rendition of the song during their 2022 DNA Tour stop in Toronto. During the performance, Drizzy called "I Want It That Way" "one of the greatest songs of all time" and recounted a girl approaching him to dance to the song at his bar mizvah.

The Manhattan venue was packed from wall-to-wall, where Chanel and Hermès handbags were gifted to attendees, while a game show was also held, where cash prizes worth up to $1 million were given out.

During one point of the evening, the Iceman rapper delivered a sentimental speech about the next decade of his life. "Tonight isn't about a tour, an album release, or a bunch of videos we shot," Drake told attendees. "It's about being alive, staying alive."

Earlier in the week, Drake hosted a birthday celebration in his hometown of Toronto, where he linked up with close friends and longtime collaborators at the CN Tower, including Popcaan. He later boarded a flight to New York alongside his mother, Sandi Graham, and entourage aboard his customized Boeing 767, Air Drake, before dining at SoHo restaurant Mamo.

The week also delivered new record certifications for the chart-topper. On Friday (Oct. 23), the RIAA credited Drake with 30 new certifications, making him the first artist to surpass 350 million certified units, with a record 18 diamond plaques, and a platinum certification for Iceman five months after its release.