Drake Goes Full Captain Jack Sparrow on Night 2 of His Wildest Birthday Bash Yet, Parrot Included
Drake has never been one to let a milestone birthday pass quietly. Over the years, the Toronto rapper has turned his annual celebration into a themed spectacle, from a re-bar mitzvah to a cowboy-themed costume night. This year, the birthday celebration of Drake has stretched across multiple cities and several nights.
The occasion is a big one. Drake officially turned 40 on Saturday, October 24, and he started the festivities early with friends in his hometown of Toronto, including a gathering at the CN Tower. From there, he flew to New York City with his mom and kicked off the main event.
The first big party took place on Friday, October 23, at Casa Cipriani in Manhattan. Drake arrived in a sparkling black tuxedo jacket, a bow tie and wide-leg trousers, and more than 400 guests were on hand. The star attraction was a surprise performance from the Backstreet Boys.
The night was packed with extras. Guests could play a game show with cash prizes ranging up to $1M, and the giveaways included Chanel and Hermès items. Outside the venue, Drake was presented with a red Ferrari as a birthday gift.
Drake dazzles as Jack Sparrow at night 2 of his birthday celebration. https://t.co/jpsAH1fgll
— The XO Show ™ (@latenightxoshow) October 25, 2026
Then came the second night, and that is where the Jack Sparrow moment arrives. A video from Saturday’s celebration shows Drake in a white shirt and red pants with a gray parrot perched on his arm, a look labeled as a Jack Sparrow-style turn from the rapper. For fans of Disney’s ‘Pirates of the Caribbean’ franchise, the swagger and the parrot made the reference easy to spot.
The Saturday event was held at Delilah in New York, where Drake wore an animal-print Chrome Hearts jacket over a white shirt, red leather pants and dark boots. It was a very different vibe from the formal tuxedo of the night before. The bird, of course, was the real scene-stealer.
The second night drew another round of celebrities. Reported attendees included Travis Scott, Jack Harlow, Alix Earle, Adam22, Lena The Plug, Loe Shimmy, Giggs, Ashtin Earle and Landon Barker. According to Vogue, Drake also took the stage during the evening and was joined by Popcaan.
An attendee also said another party was planned for Saturday night, which suggests the weekend could have still more surprises. That fits the pattern of the week. Drake has been moving from one event to the next rather than packing everything into a single evening.
The pirate look continues a long tradition. For his 31st birthday, Drake threw a bar mitzvah-themed party in West Hollywood with sports arcade games and baby photos on the walls. At 35, he went with a Narcos-themed costume party in Los Angeles and dressed as a cowboy, tying it to the album ‘Certified Lover Boy’.
He has also gone with a mobster look for his 33rd and a 2000s theme the year before that. In other words, the costume is part of the brand. Showing up as a swashbuckling pirate fits neatly into that history.
The Backstreet Boys appearance had a built-in backstory. In July 2022, the group brought Drake onstage in Toronto and introduced him as their sixth member before performing ‘I Want It That Way’. Drake told the crowd that night that the song had been the theme to his bar mitzvah.
That callback made the surprise performance feel personal rather than random. It also showed how much thought goes into these celebrations. The mix of nostalgia, luxury and humor is a signature of the artist’s party style.
Taken together, the week has been a showcase of Drake’s talent for turning attention into an event. The parties delivered viral clips, celebrity guest lists and plenty of fashion talk, including a shawl look that had the internet calling him a fall style muse. Even the smaller details, like a parrot on his arm, have become part of the conversation.
It is also a reminder of how closely fans follow his every move. A short clip of a costume can spread quickly, and a milestone like a 40th birthday only raises the stakes. Whatever comes next, this year’s celebration is already one of his most memorable.
What do you think of Drake’s Jack Sparrow-inspired look at his 40th birthday bash?
Have something to add? Let us know in the comments!
