Drake’s ‘Lavish’ 40th Birthday Included Him Performing with Backstreet Boys, Giving Out $1M Cash Prize (Exclusive Source)
Some birthdays are quiet. Drake’s 40th was not one of them. On Friday evening, October 23, 2026, the Canadian rapper celebrated his milestone birthday at Casa Cipriani in Manhattan, New York City, in a party described as very lavish but tasteful, elegant, over the top and expensive — and, in a twist that says a lot about him, he spent much of the night giving things away, even though it was his own birthday.
According to an exclusive source who attended the festivities, it was a memorable night from start to finish. Drake, who turned 40 on Saturday, October 24, 2026, was at the centre of it all, chatting, smiling, and then taking the stage for a moment no one in the room is likely to forget.
A Lavish Night at Casa Cipriani
The venue set the tone. Casa Cipriani in Manhattan hosted the bash on Friday evening, and the decor was elegant and over the top in equal measure. Lavish, but tasteful, was how the night was described — expensive without feeling careless, and grand without losing its warmth.
About 400 people attended, according to another source. The insider said Drake chatted with many different women all night and kept a huge smile on his face, which fits the picture of a host who was enjoying his own party as much as his guests were.
Gifts, Bags and Cash Prizes
Despite it being his birthday, Drake gave out gifts. The giveaways included Chanel and Hermès bags, along with cash prizes of varying sums. The cash prizes started at $10,000, and the biggest prize totaled $1 million.
The article does not state who won the top prize, or how it was won, and no method is claimed here. What is clear is the scale of the gesture: a birthday guest list that went home with luxury bags and cash, with $1 million as the headline prize of the night.
Backstreet Boys Take the Stage
The Backstreet Boys performed at the bash, and that alone would have made the night special. The members named are Nick Carter, AJ McLean, Kevin Richardson, Brian Littrell and Howie Dorough, all five of them onstage together.
Then came the moment that turned a great party into a story. Drake joined all five members onstage for their 1999 hit, “I Want It That Way.” The article calls it his onstage birthday moment, a gift to himself, and it was not his first time sharing that song with the band — he had previously performed it with them during a 2022 Toronto concert.
A Second Party, and a Historic Year
The night did not end the story. A second birthday party was said to follow on Saturday, which means the 40th celebrations stretched across the weekend, not just a single evening.
The New York celebration also coincided with a career milestone. On Friday, Drake received 30 new RIAA certifications, making him the first artist to surpass 350 million RIAA-certified units, as reported via Billboard. It came near the end of a historic year in which he broke Michael Jackson’s long-standing record for most No. 1 songs by a solo male artist in May, with “Janice STFU” debuting at the top of the Billboard 100, a couple of weeks after a May 15 triple-album release: ICEMAN, HABIBTI and MAID OF HONOUR.
Put together, the night makes sense as a milestone in every sense. A lavish but tasteful party, about 400 guests, luxury bags and cash prizes, a stage shared with the Backstreet Boys, and a career record being set in the same week. Drake turned 40 by giving, by performing, and by marking the moment with the people around him — and, for one song at least, by becoming, for a few minutes, the sixth Backstreet Boy.
