Drake Turned 40 With a Backstreet Boys Surprise, a $1 Million Giveaway, and One Night Nobody Will Forget
Drake Turned 40 With a Backstreet Boys Surprise, a $1 Million Giveaway, and One Night Nobody Will Forget
Most people get a cake on their 40th birthday. Drake got a boy band, a room full of designer handbags, and a game show where the top prize was $1 million. And that was only the first party.
The Canadian rapper turned 40 on Saturday, October 24, 2026. He started the celebrations a night early, on Friday, October 23, with a lavish bash at Casa Cipriani in Manhattan, New York City. According to PEOPLE, which spoke to an attendee, about 400 people were there. And if the reports are anything to go by, Drake was not the one collecting presents. He was the one giving them away.
The party where the birthday boy gave everyone else gifts
An insider described the night to PEOPLE as “so elegant, over the top and expensive.” The room, the source said, was decorated in a way that was lavish but still tasteful. Drake arrived in a sparkling black tuxedo jacket with a bow tie and wide leg trousers, ready for a black tie night.
Then came the giveaways. Guests were handed Chanel and Hermes bags, according to PEOPLE and TMZ. On top of that, Drake turned part of the evening into a game show, with cash prizes on offer. The prizes started at $10,000, the PEOPLE source said, and the biggest prize totaled $1 million. Reports differ on whether the top prize was actually won, but nobody disputes the scale of it. For one night, the birthday boy played game show host with his own money.
It is a very Drake way to mark a milestone. He has built a career on generosity as spectacle, on turning a lyric into a real life moment. This time the moment was not a music video. It was a ballroom full of his closest people, all going home with something expensive in their hands.
Then the Backstreet Boys walked out
The biggest surprise of the night was not a bag or a cheque. It was a boy band.
The Backstreet Boys performed at the bash, and Drake joined them onstage to sing their 1999 hit “I Want It That Way.” The group, made up of Nick Carter, AJ McLean, Kevin Richardson, Brian Littrell and Howie Dorough, turned a 40th birthday party into a full on 1990s singalong.
This was not the first time Drake and the band have shared a stage. He previously performed the same song with them during a 2022 concert in Toronto, where they introduced him as their sixth member. The song clearly means something personal to him. He has spoken before about hearing it at his bar mitzvah, when a girl he liked asked him to dance to it, a moment he described as the first time he felt he had a shot at being cool.
On Friday night in New York, that memory came full circle. Only this time he was not a teenager hoping for a dance. He was a 40 year old superstar singing the chorus with the band itself, in front of 400 of his friends.
A week of celebrations, from Toronto to New York
The New York bash capped off several days of birthday celebrations. Earlier in the week, friends surprised Drake with a collage of memories at a private gathering at the CN Tower in Toronto. Popcaan was among the guests, according to reports. Drake then travelled to New York with his mother, Sandi Graham.
Reports also said Drake was presented with a red Ferrari outside the venue, and that he stopped to pose for photographs with fans before leaving. In a clip shared from the night, he reflected on reaching 40 in an emotional speech to the crowd, saying: “Tonight is just about being alive, staying alive.”
PEOPLE also reports that the New York celebration will be followed by a second birthday party on Saturday, the day he actually turned 40. If Friday was the warm up, Saturday may be even bigger.
A record breaking birthday week
The party came at the end of what has already been a historic year for Drake. PEOPLE notes that the birthday celebrations coincided with a career milestone reported by Billboard: the Recording Industry Association of America awarded him 30 new certifications on Friday, making him the first artist ever to surpass 350 million certified units in the United States. Reports say that total includes 18 Diamond records, including his album Views and hit singles “In My Feelings” and “Marvin’s Room.”
Earlier in 2026, he also broke Michael Jackson’s long standing record for the most No. 1 songs by a solo male artist, according to PEOPLE. That came after a massive triple album release on May 15, with three records, ICEMAN, HABIBTI and MAID OF HONOUR, arriving at once.
Put together, it is quite a way to enter a new decade. Most artists would be happy with one of those milestones in a year. Drake collected them in a single birthday week, then celebrated by giving a million dollars away.
Why this party will be talked about for a while
Celebrity birthday parties are usually forgotten within a week. This one has a few things going for it that will keep people talking.
First, the surprise was genuinely surprising. The Backstreet Boys are not a random booking. They are tied to one of Drake’s most personal pop memories, and watching him sing their biggest hit with them again felt like a full circle moment rather than a stunt.
Second, the generosity was the story. Birthday coverage usually focuses on what the star wore or who showed up. Here, the headline was what the guests took home: designer bags, cash prizes, and a night they will be telling people about for years.
And third, the timing was perfect. Drake turned 40 at a moment when his chart record is untouchable and his cultural footprint is as large as ever. The party did not feel like a nostalgia trip. It felt like a victory lap.
It is the same spirit that runs through the biggest music moments of recent weeks. When Jay-Z reportedly picked himself to headline the 2027 Super Bowl halftime show, fans reacted to the sheer confidence of it. When Harry Styles was filmed with an autograph seeker in New York, the story flipped once the other man spoke up. And when Janet Jackson honored Missy Elliott at the Dancers Against Cancer gala, the night was about friendship as much as fashion.
Drake’s 40th fits right into that run of unforgettable music moments. Only his version came with a boy band, a ballroom, and a million dollar game show.
Forty looks good on him. And if Saturday’s second party is anything like Friday’s first, the celebrations are only just getting started.
