It makes sense that Drake is from Toronto. Just as he could only be from Toronto—a generally agreeable and insanely clean metropolis filled with whitewashed, modern architecture—the Canadian city could only produce a megastar like Drake. He's equal parts contemplative and idealistic, just like his hometown, and he's especially susceptible to loneliness, which Toronto seems like it could easily foster.

Much has been said about Drake's allegiance to Toronto, for despite buying a sprawling mansion in SoCal, he has continued to pledge his love for his hometown via his songs and even tattoos. Drake's most visible love letter to his city, though, is OVO Fest, a concert that he has organized, curated and headlined since his breakout year in 2009.

Now in its fourth year, Drake's OVO Fest (named after his October's Very Own imprint/crew) ambitiously hoped to expand itself to a two-day festival, featuring performances from electronic/R&B sensations Frank Ocean and James Blake, as well as Drake and special guests. However, due to an unexpected vocal chord injury suffered in the midst of his Australian Tour, Ocean was forced to pull out of the festival and it quickly condensed to one motley day that would feature Blake, Drake, new addition Wale and those special guests, who in the past have included Rick Ross, Snoop Dogg and 2 Chainz.

This would be a good time to consider how self-serving it is (or could be) to curate a festival and make yourself the headliner every single year, and to be fair, it sounds bad, but with Drake it's a different game. His fans and the city of Toronto have and will continue to want a Drake concert with such fervor that any additional acts he throws on the bill are merely for his enjoyment and are experienced by fans as added bonuses. Sprinkles on the already-delicious (so to speak) triple scoop of ice cream.

Anyway, with a day plucked from his precious Fest, Drake, ever the overachieving do-gooder, had to make up for Ocean's unfortunate absence in a big way, and of course, he did. The show, which took place on Monday, August 5th, a civic holiday in Canada, was an exercise in fan appreciation, one thing Drizzy has always been an expert on.

After a riveting opening set by Blake—admittedly an unlikely pal to the rapper, despite his recent collaborations with both RZA and Kendrick Lamar—who floated through hits like "The Wilhelm Scream," "CMYK" and "Retrograde" to a buzzing audience that started to fill out as anticipation grew for the evening's headliner. If the crowd—filled primarily with tweens, local high schoolers and canoodling couples—was excited to see Blake, it was slightly hard to tell, but by the end of his 35-minute set he did manage to coerce a few bro'd out crews to sway to his catchier tunes.

Following Blake was a concise run-through of jams by D.C. representer Wale. After touching on his lady-friendly cuts like "Lotus Flower Bomb" and "LoveHate Thing," from his recent No. 1 album The Gifted, his set seemed to come to an abrupt halt, as there were bigger things brewing. With less than a half hour before the evening's headliner was scheduled to take the stage, there were pyrotechnics to be handled and lights to be arranged. The city was out to see its son, after all, and OVO made sure to deliver him promptly and properly.

As the lights went down on Molson Canada Amphitheatre, Drake emerged to perform his stadium-status single "Headlines" to a receptive crowd that really had no idea what he had in store for them. Quickly, he got into "Crew Love," a standout cut from his Take Care album, with an assist from fellow hometown crooner The Weeknd, who sounded as gloriously sultry as ever over the stadium's booming sound system. With his fans buzzing, Drake hinted at what was to come when he invited Big Sean onstage for a rapid-fire set of his G.O.O.D. Music hits ("Clique," "Mercy") and a team-up performance of Drake's recent single "All Me," which features Sean and 2 Chainz.