“This is the most important night of my life,” Drake told the sold-out Toronto crowd at the kick-off concert for his October World Weekend festival on Thursday night. He’s the biggest artist in the world, so you’d imagine he’s had many Important Nights™, but it didn’t sound like he was hyperbolizing. The show, dubbed “All Canadian North Stars,” was a four-hour-plus love-in featuring some of the most iconic names in the Great White North’s hip-hop and R&B history—fittingly taking place at History, the rapper’s venue. It’s music that The Boy himself clearly was a devout student of as a kid, along with a generation of old heads who grew up on these artists in the ’90s and early ’00s.

“The streets we walk, the restaurants we eat at, the clubs that we go to, the way that we speak, the aspirations and dreams that we have were shaped by each and every one of these individuals for me,” Drizzy said, before handing it over to Rascalz, Checkmate, Kardinal Offishall, and the gang to close out the night with “Northern Touch.”

While the concert was meant to be an aperitif before October World’s headlining shows at the Budweiser Stage—Chris Brown and Lil Baby on Friday, and a Young Money reunion with Lil Wayne and Nicki Minaj on Monday—for the noticeably older crowd at History, this was the main event. Curated by The Boy and local DJs Starting From Scratch and Charlie B, and boasting performances by MuchMusic and Flow 93.5 mainstays like Maestro Fresh WesChoclairk-os, and Jully Black—along with some very special guests—the evening was an instant Canadian Heritage Minute. A night when the artists who paved the way for today’s Drakes and Weeknds finally got the flowers they deserved. Here are the best moments we witnessed at the once-in-a-lifetime showcase.