Every year, Drake brings his guest-heavy OVO Festival to his Toronto hometown, and this year’s edition, which ended at Molson Canadian Amphitheater last night, had a more nostalgic theme than previous years. OutKast headlined the first of the festival’s two nights. And while Drake’s headlining set last night featured a ton of his contemporaries — J. Cole, YG, Trey Songz, PARTYNEXTDOOR, DJ Khaled — his biggest moments came alongside rap and R&B legends who made their deepest impact a decade or more ago. The show started with Lauryn Hill performing her immortal “Doo Wop (That Thing),” turning it into a medley with Drake’s recent single “Draft Day,” which samples “Doo Wop.” Midway through the show, Usher came out to do a five-song mini-set, and the only new song he sang was “Good Kisser.” And toward the end, 50 Cent and his reunited G-Unit did a surprise mini-set. Below, watch fan-made videos of Drake and Hill doing “Doo Wop” and “Draft Day,” of Usher doing “Confessions Part 2″ and “Lovers And Friends,” and of 50 making his dramatic entrance while doing “What Up Gangsta?”

I am so jealous of everyone in Toronto; this looks like too much fun. (There was originally supposed to be a rift-mending performance of a new song with Chris Brown, but Brown was prevented from entering Canada.)

[Photo by George Pimentel, via Getty Images]