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Popcaan Joins Drake's 40th Birthday Celebration in New York as the OVO Family Turns Out for Night Two

By Ras MahddyOctober 27, 2026 at 10:39 AMTrending

Popcaan joined Drake, Bow Wow, Sexyy Red and more for night two of Drake's 40th birthday celebrations in New York City, with the second night held at Lady Delilah on Drake's actual birthday, Saturday, October 24. Drake's father Dennis Graham and his godfather Hal gifted him a custom Birkin bag bearing the face of his mother Sandra Graham, and Drake gave flowers to Bow Wow and Lil Wayne during the night. Popcaan, who signed with Drake's OVO Sound label in 2019, was part of the inner-circle guest list — though his appearance does not confirm any upcoming collaboration or new release.

Popcaan Joins Drake's 40th Birthday Celebration in New York as the OVO Family Turns Out for Night Two featured image

(ReggaeVibeMedia.com) - Popcaan was in the building for night two of Drake's 40th birthday celebrations in New York City, standing shoulder to shoulder with the OVO family as the Canadian superstar marked the milestone in style.

The second night landed on Drake's actual birthday, Saturday, October 24, with the party moving to Lady Delilah. Alongside his father Dennis Graham, Drake spent the night with Bow Wow, Sexyy Red, Loe Shimmy, Mack Maine and Popcaan — a guest list that read like a family reunion as much as a birthday party.

The gift that stole the night came from Drake's father and his godfather Hal: a custom Birkin bag decked out with OVO logos and symbols, carrying the face of Drake's mother, Sandra Graham. It turned a luxury flex into something far more personal — a son's birthday, marked by the people who raised him.

For dancehall fans, Popcaan's presence is no surprise. The Jamaican star signed with Drake's OVO Sound label in 2019 and released projects like "Fixtape" and "Great Is He" through the label, and the two linked up with PartyNextDoor on "Twist & Turn." Seeing the Unruly Boss at a family-level celebration says plenty about where he sits in Drake's inner circle — not a feature artist passing through, but family.

The night was not only about partying. Drake took a moment to give Bow Wow and Lil Wayne their flowers, saying that without them, he would not be where he is in the music industry. The Lil Wayne nod carries real history: Wayne brought Drake into Young Money in 2009, and Mack Maine, who was in the room, has been part of that camp from the start.

All of this followed a big opening night on Friday, October 23, at Casa Cipriani. The Backstreet Boys pulled up to perform and brought Drake onstage for their 1999 hit "I Want It That Way" — a song Drake has said goes back to his bar mitzvah, when a girl he liked asked him to dance. Night one also saw him give away $1 million worth of prizes.

The celebrations also arrived as Drake's "Janice STFU" debuted at No. 1 on the Billboard Hot 100. So Drake is turning 40 with a chart-topper, a room full of collaborators, and the dancehall world represented right at the centre of it.

For Popcaan, the appearance is another reminder of how far the Unruly Boss's reach now runs — from St. Thomas to the biggest rooms in New York, still carrying Jamaica with him. And for fans already wondering whether this birthday energy carries over into new music, one thing is worth saying plainly: Popcaan showing up does not confirm an upcoming collaboration or a new release. For now, it is simply a moment — dancehall and hip-hop, family to family, under one roof in New York.

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