Drake has officially entered his forties, and he did it the only way Drake knows how: big. The Toronto superstar celebrated his 40th birthday with a lavish party in New York City on Friday night, and the evening’s biggest surprise came from a boy band he has loved since childhood.

Here’s what went down, based on reporting from Billboard and Complex, which both cited earlier reporting from TMZ.

A packed night at Casa Cipriani

The party took place at Casa Cipriani in Manhattan on Friday, October 23, just hours before Drake officially turned 40 on October 24. According to Complex, more than 400 friends and family members packed the venue wall to wall.

The guest experience was, by all accounts, over the top. Billboard reports that attendees received luxury giveaways including Chanel and Hermès handbags. A game show was also held during the night, with cash prizes ranging from tens of thousands of dollars up to $1 million, according to the reports.

The Backstreet Boys are back (again)

The musical highlight was a surprise performance by the Backstreet Boys. The group played for the crowd before bringing Drake onstage to join them on their 1999 hit “I Want It That Way.”

If that pairing sounds familiar, there’s a reason. Back in July 2022, the Backstreet Boys brought Drake onstage during their DNA World Tour stop at Toronto’s Budweiser Stage, introducing him as their “sixth member.” That night, Drake told the crowd the song soundtracked a formative memory from his bar mitzvah, when a girl he liked asked him to dance.

“That was the first time I ever felt acknowledged, and the first time I ever felt like I had a shot at being cool,” he said at the time, calling it “one of the greatest songs of all time.” Four years later, the same song soundtracked another milestone.

‘About being alive, staying alive’

Amid the spectacle, Drake took a moment to get reflective. Speaking to the room, he made clear the night wasn’t about business.

“Tonight isn’t about a tour, an album release, or a bunch of videos we shot,” he told guests, according to Billboard. “It’s about being alive, staying alive.”

It was a notably sentimental note from an artist better known for chart dominance and big-budget spectacle than for public introspection.

A birthday week, not just a birthday

The New York bash capped several days of celebrations. Earlier in the week, Drake gathered with friends in his hometown of Toronto at the CN Tower, where he was surprised with a collage of photos and memories. Dancehall star Popcaan was among those in attendance.

He then flew to New York with his mother, Sandi Graham, and his entourage aboard Air Drake, his customized Boeing 767, and was spotted dining at SoHo restaurant Mamo on Thursday night, October 22.

A record-breaking present from the RIAA

The timing of the party lined up with a major career milestone. On Friday, the Recording Industry Association of America awarded Drake 30 new certifications, making him the first artist to surpass 350 million RIAA-certified units, according to Billboard.

Among the highlights:

  • Views, “In My Feelings” and “Marvin’s Room” were newly certified Diamond
  • “God’s Plan” reached 2x Diamond status
  • His latest album, Iceman, went platinum five months after its May release
  • Drake now holds 18 Diamond plaques, extending his record for the most of any artist

Why it matters

Celebrity milestone birthdays have become events in their own right, and Drake’s 40th checked every box: an exclusive venue, a guest list in the hundreds, eye-popping gifts and a surprise headliner. But the Backstreet Boys moment gave the night something money can’t buy, a callback to a story Drake has told about his own awkward teenage years.

The wrap-up

Drake’s 40th birthday was equal parts blowout and nostalgia trip, with a chart-history milestone landing the same day. Few artists can say they celebrated turning 40 by singing their favorite childhood song with the band that made it, while collecting a fresh stack of record-breaking plaques. For Drake, it was just another week.

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