Drake turns 40 today, and the Backstreet Boys showed up to help him celebrate. The legendary boy band surprised him with a performance at his birthday party in New York City on Friday night, and Drake ended up on stage singing “I Want It That Way” right alongside them.
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The party went down at Casa Cipriani, where Drake hosted more than 400 friends and family members. According to TMZ, Drake had no idea the group would be performing, and video from the night shows him completely losing it once he realized what was happening. He did not stay in the crowd. He did not just record on his phone. He grabbed a spot on stage and sang the 1999 hit with Nick Carter, Howie Dorough, AJ McLean, Brian Littrell and Kevin Richardson harmonizing behind him.
The song means more to Drake than a karaoke moment. He has said “I Want It That Way” is tied to one of his earliest memories of feeling accepted, so singing it with the actual Backstreet Boys on his 40th hit different.
Drake dressed the part for the night, arriving in a tuxedo with a shimmering jacket. And while it was his birthday, he was the one handing out gifts. Guests were treated to designer handbags from Chanel and Hermès, and Drake turned part of the evening into a game show where lucky attendees could win cash prizes starting in the tens of thousands and going all the way up to $1 million.
The New York party capped off a full week of celebrating. Earlier in the week, Drake held a private gathering at the CN Tower in his hometown of Toronto, where friends surprised him with a collage of memories. He then flew to New York on Air Drake, his customized Boeing 767, with his mother and his crew, and was spotted having dinner at Mamo in SoHo on Thursday night before the big bash.
Over the top birthdays are nothing new for him. For his 32nd, he recreated the “106 & Park” set for an early 2000s themed party. In 2023, Bryan Cranston and Aaron Paul showed up working behind the bar after Drake booked their catering company without knowing the “Breaking Bad” stars would be serving drinks.
Drake turns 40 with a party that will be hard to top, and a sing along with the Backstreet Boys that he clearly will not forget.
