On October 23, 2026, Drake began celebrating his 40th birthday ahead of his actual birthday on October 24. Over the weekend, the rapper attended a series of parties in New York City. At Casa Cipriani in Manhattan, Drake celebrated with around 400 guests, who were treated to a surprise performance by the Backstreet Boys. The 90s boy band performed “I Want It That Way”, with Drake joining the group.

On the second evening in New York City, October 24, Drake celebrated at Delilah. This evening featured appearances and performances by Bow Wow, Sexyy Red, and Jamaican dancehall star Popcaan, whose appearance reportedly marked his first-ever performance in the US after years of visa difficulties. Three days later, celebrations continued with a big surprise in Houston.

Videos by VICE

On Tuesday, October 27, Jeff Ross, known as the “Roastmaster General”, surprised the rapper with a roast set. Though Drake praised Ross afterward, he actually requested to be roasted by actor Jim Carrey.…