Happy 40th, Drake!

The rapper celebrated his entry into middle age with a lavish Cipriani birthday bash — complete with Hermès party favors.

In 2011, at the tender age of 25, Drake was already so aware of the fleeting nature of life that he popularized the acronym yolo in his hit song “The Motto.” How must the superstar rapper be feeling now that he’s 40?

On October 23, surrounded by 400 well-wishers who affectionately refer to him as “the boy,” Drake celebrated his milestone at the Cipriani on 42nd Street. It was the beginning of his miniature birthday-party residency, followed by a bash on the 24th at Lady Delilah attended by the likes of Jack Harlow, Travis Scott, and Alix Earle. The first of these events was a dressier and more upscale affair, and the rapper rang in the occasion as any newly middle-aged person might: by retreating into the warm embrace of nostalgia. Special guests the Backstreet Boys provided background vocals while he did karaoke to their 1999 hit “I Want It That Way.” Per band member A J McLean, the appearance was one of only two wishes Drake had for his birthday, the other being a performance by Sade. Assuming the ability to delete Kendrick Lamar from the collective consciousness was not on offer, what else could one give this fellow who has everything? It wasn’t even the first time Drake got to live out his Backstreet Boys fantasy; he sang the same song with them in his hometown of Toronto in 2022. 

Drake, instead, took the opportunity to give. Guests walked away with Chanel and Hermès handbags, and some participated in a Deal or No Deal–style game, winning cash prizes of up to $1 million. (The game’s briefcases, of course, were inscribed with DRAKE STAKE.) On parting, the artist gave his guests an invaluable gift: his words of gratitude. In a toast that has since gone viral, he thanked everyone for attending, noting that the party was “not about a tour, or an album release, or a bunch of videos that we shot, or a fragrance, or a Nike shoe,” but rather “being alive.” A poet lives on.

Thank you for subscribing and supporting our journalism. If you prefer to read in print, you can also find this article in the November 2, 2026, issue of New York Magazine.

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