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.

What followed these quick guest slots, though, was so grandiose… so epic, that the only way to properly give an explanation of the events is in bullet-point format (below), for the sake of not ranting for pages upon pages. Before that, though, it should be noted that sprinkled throughout the insane number of guest appearances, was Drake delivering some of his most popular songs—he has so many—and reminding the crowd of the unique balance of earnestness and cockiness in his artistic statement.

When he's onstage alone, Drake is all bravado, all the time. While not exactly a hyper-masculine presence like his rap (and some of his R&B) peers, he's more of a one-man Rat Pack, equipped with enough confidence, charisma and most importantly, a strong back catalogue, to properly possess the stage for as long as he wants. His creative maturation helps, too.

From hits from his So Far Gone days to his latest vulnerability-celebrating songs like "Girls Love Beyonce" and "The Motion," Drake has found ways to keep a clear through-line in his worldview while finding new ways to express it. What's more, he truly walks the line between being a heartthrob and "one of the boys," attracting both men and women to swoon throughout the night. He could've done Jay Z and JT's Legends Of The Summer Tour all on his own.

Regardless, the remainder of Drake's 2013 OVO Fest saw:

- French Montana emerging and performing club killers "Ain't Worried About Nothin'" and "Pop That."
- Drake inviting TLC (seriously) onstage for updated renditions of classics like "Waterfalls" and "Scrubs."
- Born Sinner J. Cole running through choice cuts from his catalogue like "Nobody's Perfect," "Power Trip" (alongside Miguel, who was also there) and "Forbidden Fruit" to a rabid crowd.
- Bad Boy icon Diddy introducing a two-track glorious set from Ma$e, including a nostalgia trip to the days of "Mo Money, Mo Problems."
- Former Drake protege and rising star A$AP Rocky playing hits like "Fuckin' Problems" and "Wild For The Night" to flocks of excited teen girls.
- Drake mimicking Kanye West's "Diamonds" verse, but remixing it to say "What's up with you and 'Ye, man? / Y'all okay man?" before inviting Lord Yeezus onstage for a highlight-reel performance that included renditions of "New Slaves" (with Yeezy basked in only red light), "All Of The Lights" and "Can't Tell Me Nothing."
- YMCMB chief and one of Drake's earliest cosigners Lil Wayne blessing his former mentee with praise in front of his hometown. The duo went on to perform collaborative hits like "The Motto," "HYFR" and "Bitches Love Me." Before leaving the stage, Weezy would admit, "I'm happy to be a piece of this puzzle."

At times, what was even more striking than Drake’s unfolding all-star show was his heartwarming interactions with his peers. There was a sense of likability and goodwill between him and every one of his collaborators that seemed too genuine to be faked. Of course, as he's wont to do, he hugged each guest, and went on to say kind words (Kanye is "the reason I'm rapping," Wale is "one of the deepest minds in this game," "Without Lil Wayne, there would be no Drake") about every single one of them. Assembling so much starpower couldn't have been easy, and it seems unlikely that Drake could've actually made any money from OVO Fest, but when you're presenting such an elaborate gift to your city, profits hardly matter.

So, after nearly two hours of surprise guest-after-surprise guest, the audience was visibly winded (and blunted, and drunk, and overjoyed), but Drake still wasn't done. As OVO Fest came to a close, Toronto's idol stood alone in the spotlight on a stage that he'd proven he deserved. Looking out into an audience of roughly 20,000, he smugly asked, "Oh, you think we're done?" and followed that with some final pleasantries for his city, before politely asking if he could "bring it home." Everybody was happy to play along, knowing full well that this was Drake's friends' show more than his own.

Still, for his final triumverate of hits, Drake spit his blistering verse off recent Migos single "Versace" and sang a hook and a verse from DJ Khaled's anthemic "No New Friends," before finally preparing his Canadian fans for a performance of their country's "new national anthem" with his fire-starting single "Started From The Bottom." Though the tune is nearly seven months old now, it sounded fresher and more grandiose than ever, and served as a perfect summation for the night. Drake started from the bottom, now he's an icon among icons.