Drake Celebrates 40th Birthday With Backstreet Boys Performance

A Milestone Celebration in New York City

The Drake 40th birthday festivities reached a peak on Friday night, October 23, at the members-only club Casa Cipriani in New York City. The Toronto-born superstar, known for his dominance in R&B and hip-hop, hosted more than 400 guests for the event, which took place just hours before his official birthday on October 24. The evening was characterized by extreme luxury, with reports indicating that guests received high-end giveaways, including Chanel and Hermès handbags. Additionally, the party featured a game show where attendees could win cash prizes ranging from tens of thousands of dollars to a grand prize of $1 million.

During the event, the rapper took a moment to address his guests and reflect on the significance of reaching the age of 40. He emphasized that the gathering was a personal milestone rather than a professional promotion.

"Tonight isn’t about a tour, an album release, or a bunch of videos we shot. It’s about being alive, staying alive."

— Drake

Surprise Performance With the Backstreet Boys

The highlight of the night’s entertainment was a surprise appearance by the Backstreet Boys. Band members Nick Carter, Brian Littrell, AJ McClean, Kevin Richardson, and Howie Dorough all took the stage to perform their 1999 classic hit, "I Want It That Way." Drake joined the group as a "bonus" member, providing vocals throughout the performance and taking over the vocal outro of the ballad. During the bridge of the song, Howie Dorough integrated a line from Drake’s own hit, "Hold On, We’re Going Home."

The performance held deep personal significance for the artist. "I Want It That Way" peaked at No. 6 on the Billboard Hot 100 in 1999, a year when Drake was 13 years old. He has previously described the track as "one of the greatest songs of all time," noting that it soundtracked a pivotal moment at his bar mitzvah when 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."

— Drake

This collaboration followed a previous appearance in July 2022, when the group brought him onstage during their DNA World Tour stop at Toronto’s Budweiser Stage, introducing him as their "sixth member."

Personal Reflections and Childhood Tributes

In the hours leading up to his 40th birthday, the rapper shared a series of personal childhood photographs on social media, offering fans a glimpse into his early life. One notable image featured a young Drake sitting on the hood of a car while holding a copy of the book My Teacher Fried My Brains. He accompanied the photo gallery with a brief, sentimental message directed at his younger self.

"I accept you for you."

— Drake

The New York celebration was the conclusion of a week-long series of events. Earlier in the week, he celebrated in his hometown of Toronto at the CN Tower, where friends including Popcaan surprised him with a collage of memories. He eventually traveled to New York accompanied by his mother and his entourage aboard Air Drake, his customized Boeing 767. On the night of October 22, he was seen dining at the SoHo restaurant Mamo.

Historic RIAA Career Milestones

The 40th birthday celebration coincided with a historic achievement in the artist's professional career. On October 23, the Recording Industry Association of America (RIAA) issued 30 new certifications for his catalog. This update officially made him the first artist in history to surpass 350 million RIAA-certified units.

His record-breaking RIAA portfolio now includes several high-profile updates:

• 18 Diamond plaques in total, extending his record for the most by any artist.

• "God’s Plan" reached 2x Diamond status.

• Views, "In My Feelings," and "Marvin’s Room" were all newly certified Diamond.

• His most recent album, Iceman, was certified Platinum just five months after its release in May.

The combination of these commercial records and the high-profile birthday bash solidified the week as a major landmark for the artist as he entered his fifth decade.