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.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. On September 13, Carrey roasted the man himself, Jeff Ross, for his 61st birthday. Upon seeing footage of this roast, Drake publicly commented, “Wow, this is now all I want for my birthday.” Instead, he got the “Roastmaster General” himself. Footage from the roast hasn’t been released yet.The Celebration Doesn’t End ThereHouston also got in on the festivities, with multiple venues and clubs hosting Drake-themed events for his 40th birthday. The city has hosted some memorable celebrations for the rapper before. In October 2024, for instance, Drake threw a 2000s-themed party at Escape nightclub, where he had a dance-off with singer-dancer Omarion. He also visited Area 29, where he was seen “making it rain” and handing out stacks of cash. Those events were part of his 38th birthday celebrations, rather than this year’s festivities.As Drake went all out for his 40th, his three May 2026 albums reportedly won’t be competing at the Grammys in February 2027. The rapper reportedly didn’t submit any of his three albums or their songs released in May 2026. Drake is still appealing the dismissal of his defamation lawsuit against Universal Music Group over Kendrick Lamar’s diss track, “Not Like Us.” Oral arguments in the appeal are scheduled for December 4, 2026. Drake has previously criticized the Grammys, but no verified explanation links his latest decision not to submit music to the lawsuit. In February 2025, the diss track won in five different categories at the 67th Annual Grammy Awards.Photo by XNY/Star Max/GC ImagesThe post Drake Gets Unexpected Birthday Surprise After Asking to Be Roasted by Jim Carrey appeared first on VICE.