Drake rang in his 40th birthday with the Backstreet Boys, a $1 million game show and more than 400 guests at New York’s Casa Cipriani.
The rapper celebrated on Friday night (Oct. 23), hours before his official Oct. 24 birthday, with a lavish party that included a surprise performance from the Backstreet Boys. Footage shared from the event shows Drake joining the group for their 1999 smash “I Want It That Way” — a song with some history in his own life.
According to TMZ, the night also featured luxury giveaways including Chanel and Hermès handbags, while guests competed in a game show offering cash prizes of up to $1 million.
The New York party closed out several days of celebrations for the Toronto superstar. Earlier in the week, Drake marked the milestone with a private gathering at the CN Tower in Toronto, where friends surprised him with a collage of memories, according to XXL. Popcaan was among the guests.
He later traveled to New York aboard his customized Boeing 767, Air Drake, with his mother and members of his entourage, and was spotted dining at SoHo restaurant Mamo on Thursday night (Oct. 22).
Drake had already made one birthday wish public before the festivities began. In September, he said that all he wanted for his 40th was to be roasted by Jim Carrey.
The Backstreet Boys appearance, however, offered the night’s most fitting throwback.
Drake previously joined the group onstage during their DNA World Tour stop at Toronto’s Budweiser Stage in July 2022, when they introduced him to the hometown crowd as their “sixth member.” The rapper then helped perform “I Want It That Way,” weaving parts of his own “Hold On, We’re Going Home” into the song.
At the time, Drake explained that the Backstreet Boys hit was tied to one of his earliest memories of feeling accepted. He recalled hearing the song 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,” he told the crowd, before describing “I Want It That Way” as “one of the greatest songs of all time.”
Four years later, the song returned for another milestone.
Drake enters his 40s with one of the most dominant chart résumés in Billboard history. He has logged more than 400 entries on the Billboard Hot 100 — the most of any artist — and also holds the record for the most top 10 hits. His 14 Hot 100 No. 1s are the most among solo male artists.
He added another unprecedented achievement in May when Iceman, Habibti and Maid of Honour debuted at Nos. 1, 2 and 3, respectively, on the Billboard 200, making Drake the first artist to occupy the chart’s entire top three at the same time.
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