Key Takeaways

Drake celebrated his 40th birthday with more than 400 guests at New York’s Casa Cipriani, where the Backstreet Boys surprised him and brought him onstage for "I Want It That Way."

Guests received Chanel and Hermès handbags and competed for cash prizes worth up to $1 million, while Drake framed the night as being "about being alive, staying alive."

The celebration capped a birthday week that included a Toronto gathering and 30 new RIAA certifications, making him the first artist to surpass 350 million certified units.

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.…