Drake shares childhood photos and performs with Backstreet Boys at 40
Drake marked his 40th birthday on October 24 by sharing childhood photographs on Instagram and joining the Backstreet Boys on stage in New York City.
Childhood Photos Shared for the 40th Birthday Milestone
For his October 24 birthday, the artist paid tribute to his younger self on social media with a glimpse at who he was as a kid. “I accept you for you,” he wrote to himself on Instagram alongside childhood pictures posted on the eve before turning 40. In one snapshot, he sits on the hood of a car hugging his copy of the book My Teacher Fried My Brains.
Drake performs “I Want It That Way” with the Backstreet Boys at his 40th birthday celebration. https://t.co/ZupqTaXShr
Surprise Performance With the Backstreet Boys at Casa Cipriani
Stepping far beyond a typical birthday bash, Drake ushered in his 40s by performing alongside the Backstreet Boys on one of his absolute favorite pop tracks, “I Want It That Way.” The dedicated fan enthusiastically participated in the vocals throughout the 1999 track during the appearance on Friday night, October 23.
That year, the song reached No. 6 on the Billboard Hot 100 chart and dominated both Top 40 radio and MTV’s TRL countdown. Drake was 13 years old in 1999. Howie Dorough worked in a line from Drake’s own “Hold On, We’re Going Home” at the bridge. In addition to Howie, fellow members Nick Carter, Brian Littrell, AJ McClean, and Kevin Richardson all made appearances for the unexpected birthday bash held at the exclusive New York City venue Casa Cipriani.

Vocal Outro and Nostalgia for a Millennium Pop Hit
Drake wrapped up the ballad by taking on the vocal outro, crooning one of his favorite songs in a video shared on X. “Tonight isn’t about a tour, an album release, or a bunch of videos we shot,” Drake told party guests Saturday night. “It’s about being alive, staying alive.”
He once said that something about “I Want It That Way” made him feel like he was acknowledged for the first time, and felt like he had a shot at being cool for the first time. According to Drake, the Millennium track is one of the greatest songs of all time.