Backstreet Boys surprise Drake’s 40th birthday at Casa Cipriani, performing “I Want It That Way” for 400+ guests in a nostalgic ’90s pop highlight.
- October 25, 2026
AceShowbiz - Backstreet Boys made a memorable appearance at one of the most extravagant birthday celebrations of the year, performing live during rapper Drake’s 40th birthday festivities. The iconic boy band took the stage to deliver their timeless 1999 hit “I Want It That Way,” joining the rapper for a nostalgic singalong that perfectly captured the evening’s celebratory spirit.
The birthday weekend was nothing short of spectacular, set in New York’s upscale Casa Cipriani and attended by over 400 guests. Drake’s choice to bring the Backstreet Boys on board highlighted the blend of nostalgia and star power that defined the event. Their performance was a standout moment, adding a unique, unexpected touch of ’90s pop to an otherwise ultra-modern celebration.
Drake’s style throughout the weekend was as bold as his party planning. For the main event, he was dressed in a sparkling black tuxedo jacket with silk lapels, paired with pleated, wide-legged trousers and a crisp white shirt, all topped off with a satin bow tie featuring a diamond “D” pin. The rapper’s wrist was adorned with an exclusive, diamond-encrusted Rolex Cosmograph Daytona engraved with “Freeze the World,” underscoring his penchant for rare, statement-making accessories.
Generosity was another theme of the night. Guests were treated to high-end fashion gifts, including Chanel and Hermès handbags, with some lucky attendees receiving coveted Birkin bags. Beyond luxury handbags, a game-show-style giveaway dished out cash prizes starting at $10,000 and soaring up to an astonishing $1 million. This level of extravagance made it clear that no expense was spared to mark this milestone birthday.
The festivities extended beyond the black-tie affair. On the following night, Drake shifted gears with a more daring look, sporting a cheetah-print Chrome Hearts jacket paired with bright red leather pants. This outfit set the tone for a dynamic performance featuring himself alongside dancehall artist Popcaan, blending high fashion with high-energy entertainment.
The presence of the Backstreet Boys at the event reflects Drake’s appreciation for music history and his ability to seamlessly incorporate diverse influences into his celebrations. Their collaboration on stage not only thrilled guests but also created a memorable cultural moment, bridging generations of music fans.
Drake’s 40th birthday weekend was a masterclass in combining luxury fashion, star-studded performances, and heartfelt celebration. With the Backstreet Boys delivering an unforgettable throwback performance, the event transcended a typical celebrity birthday, becoming a landmark occasion marked by style, generosity, and iconic entertainment.
This article is based on reporting originally published by Vogue.