Drake marked his 40th birthday with a private celebration for more than 400 friends and family members at Casa Cipriani in New York City on October 23, 2026. The rapper, born Aubrey Drake Graham on October 24, 1986, in Toronto, turned the exclusive venue overlooking New York Harbor into a night of designer gifts, cash prizes and live music.
According to sources who spoke to TMZ, guests received Chanel and Hermès handbags. A game-show segment modeled on Deal or No Deal offered cash awards that started in the tens of thousands of dollars and climbed as high as $1 million.
A clip shared by accounts including @raphousetv2 captured one moment from the stage: a woman receiving a briefcase clearly marked $500,000. No mainstream reports have identified the recipient by name beyond the circulating video footage.
The evening also featured a surprise appearance by the Backstreet Boys. Nick Carter, Howie Dorough, AJ McLean, Brian Littrell and Kevin Richardson performed before bringing Drake onstage for their 1999 hit “I Want It That Way.”
Drake paused during the party to address the room. “Tonight is not about a tour or an album release or a bunch of videos that we shot or a fragrance or a Nike shoe,” he said, according to Complex. “Tonight is just about being alive, staying alive.”
Public estimates of Drake’s net worth in 2026 generally fall between $250 million and $400 million, with several sources citing the higher figure. The total reflects earnings from his music catalog, touring, the OVO brand, brand partnerships including a reported multi-year deal with Stake, and real-estate holdings.
Large-scale giveaways have become a recurring part of Drake’s public activity. At his third annual Strong Women, Stronger Drinks event held in August 2026 at Casa Loma in Toronto, he presented $50,000 each to 10 women and distributed luxury vehicles that included a Mercedes-Benz G-Wagon, according to reporting by Complex and other outlets. Some accounts placed the overall value of that night’s prizes above $1 million.
Earlier examples include the cash and support distributed during the filming of the “God’s Plan” music video in Miami in 2018, as documented by Variety, as well as repeated on-stage gifts during tours. Those have ranged from $100,000 handed to a fan who had finished chemotherapy to the payment of a late mother’s mortgage reported near $160,000, coverage of medical bills and college tuition, and smaller cash awards of $10,000 to $50,000 for fans holding personal signs.
The October 23 celebration at Casa Cipriani continued that pattern of high-value cash and luxury items distributed among invited guests while Drake framed the milestone itself around gratitude and the simple fact of still being present.
