Long before Drake was one of the biggest names in music, he was Jimmy Brooks on the Canadian teen drama Degrassi The Next Generation, and his character dated Hazel Aden, played by Andrea Lewis. This week, two decades removed from that storyline, Drake handed Lewis a 50,000 dollar gift in front of a room of guests at his own event in Toronto, joking that the moment felt like it was written for the occasion.
The gift came at Drake's third annual Strong Women, Stronger Drinks event, held on a Tuesday at Casa Loma, the rapper's ongoing effort to build a networking night aimed at women, a format he has credited to Shannae Ingleton Smith's What Women Want events from 2007 and 2008. Lewis was one of ten attendees who each received 50,000 dollars during the night, on top of 1,000 dollar welcome gifts handed to everyone who walked in.
Drake did not let the connection to Lewis pass quietly. This is poetic, he told the room, because me and Andrea used to be on Degrassi together, tying his current status back to a show that first put both of their names on Canadian television. Lewis, who turns 41 on August 15, 2026, posted about the moment afterward with a caption that captured the whole story in one line, my TV boyfriend stays blessing me.
The rest of the night matched the scale of that gesture. Sports journalist Kayla Grey walked away with a G Wagon, and Drake separately gifted 100,000 dollars spread across creators, business owners, and people he described simply as people I deeply respect. For a rapper who built an entire persona out of nostalgia and loyalty to where he came from, handing his old TV girlfriend a five figure check in front of a crowd was Drake doing what Drake does, just with better production value than Degrassi ever had.