Thoroughly aware the now-traditional OVO Fest surprises will garner the immediate attention of the sold-out crowd in attendance at the Molson Amphitheatre, Drake aimed to make sure the crowd had a storyline relating to his career to hold on to long after they had tweeted excitedly about who just strolled on to the stage.
After Jhene Aiko's opening set in which she performed "From Time," her collaboration from Drake's Nothing Was The Same, that first surprise guest was Ms. Lauryn Hill.
Her band had been playing reggae-inflected grooves for a few minutes before she emerged, and it was a genuine surprise when she walked out to deliver Fugees tracks like "Killing Me Softly," "Fu-Gee-La" and "Ready Or Not." Closing her set with the solo salvo "Doo Wop (That Thing)" she introduced Drake to the audience, who immediately bowed to Hill before dovetailing into his track "Draft Day," which incidentally samples the lead single off The Miseducation of Lauryn Hill.
After his moment with his mother, Drake launched into "We Made It" as the onstage screen flashed "This Is Not A Rehearsal" at the crowd. Drake insisted he would perform songs he had rarely done or had not been able to do before.
So, it was interesting to hear him perform tracks like the Lykke Li-fuelled "Unstoppable" and ballad "Bria's Interlude" (presumably to show how he has improved as a singer) from the So Far Gone mixtape before bringing out Trey Songz, whose association with Drake dated back to Comeback Season, for Gone's "Successful." Songz stuck around to perform "Na Na," and because of the randomness of some past OVO Fest appearances, you half-wondered if Hill would come back out to sing along to the chorus.
After a medley of songs from Thank Me Later including a curiously abbreviated "Over," Drake's "twin brother" J. Cole emerged to perform a couple of his biggest singles in "Can't Get Enough" and "Power Trip." Drake took the opportunity, with Cole by his side, to forcefully declare he has no beef with Kendrick Lamar after the recent tension perceived between the two due to Lamar's "Control" verse.
There was no Chantal Kreviazuk or, more surprisingly, the Weeknd, for "Over My Dead Body" or "Crew Love" as he covered the Take Care era. Drake ended that segment suspended on a mic stand above the crowd for "Marvin's Room," shouting out people in the crowd below.
The first noticeable lull in the crowd reaction occurred when Mississauga's PARTYNEXTDOOR hit the stage. Much like fellow OVO crew affiliate, Majid of Majid Jordan's appearance later in the show for "Hold On, We're Going Home," the vocals were fine, but his stage presence and body language indicated being daunted by performing in front of a large crowd at a relatively nascent period in a career. Still, PND grew more comfortable by the time Drake joined him for "Recognize."
DJ Khaled revived the crowd with a quick run-through of "All I Do Is Win" and "I'm On One," and then we were treated to a double shot of DJ Mustard beats courtesy of rising R&B singer Tinashe (along with OVO's OB O'Brien) and YG, who returned for OVO's second night after opening the first night with Outkast to perform "Who Do You Love" rocking what looked like an inaugural Raptors season jersey.
Promising the next moment to be "one of the biggest in OVO Fest history," Drake ceded the stage to Usher. With black hoodie up, he nailed the falsetto for "Climax," leading the crowd in a loud sing-along. Usher was the only special guest to really address the crowd at length, and when he made references to his connections to Canada mentioning Stratford, Ontario, the veiled Bieber reference didn't go over too well. Usher has a very good catalogue at his disposal, and he could have performed more without the in-between song banter, but "U Don't Have To Call," "Confessions" and new single "Good Kisser" underlined Usher's excellent vocal chops. While some may question Usher's ranking in the superstar stratosphere compared to past OVO guests, Drake's excitement regarding his performance was manifested when he re-emerged to tell Usher of his influence of him. He even offered a passable imitation of Usher's sideways dance, which the R&B star comfortably one-upped; he glided off the stage, with his signature swinging his chain around his neck move.
After a medley of Nothing Was the Same tracks, ending with a raucous reaction to "Started From the Bottom," Drake figured the crowd was ready for 50 Cent and G-Unit, the final surprise of the night. 50 Cent and co. gruffly delivered their rhymes, barrelling through "What Up Gangsta" alongside tracks like the underwhelming new track "Smoke," which the re-emerging Trey Songz couldn't save. Fortunately for 50, he pulled out two of his finest singles in "I Get Money" and "In Da Club" to completely win the crowd over. As G-Unit left the stage, Drake acknowledged 50 for making it possible for him to be successful.
On the surface, it seemed an incongruous statement, as 50's music bears very little resemblance to Drake's (although G-Unit recently did their own version of "0 to 100"), but 50 Cent's ruthless disruption of the mixtape ethos in the early aughts influenced the shift from the DJ to the MC on those tapes, enabling artists to build sizable fanbases before their major label debuts — something from which Drake benefitted immeasurably.
Fittingly, Drake ended OVO Fest with a mini set heavy on the non-album loosies he's released on the Internet this year. The triumphant "Trophies" was followed by the menacing head-nodder "0 to 100," but Drake wasn't quite yet done. Acutely aware of his role as Toronto Raptors global ambassador (he'd earlier shouted out players and ran the infamous Vine video of him lint rolling his pants on the screen at a game during "All Me"), he urged the crowd to let Kevin Durant, who was in attendance, hear what it would sound like if he came to play in Toronto. This drew a loud response and a "KD! KD!" chant from the crowd. It was another moment where Drake mixed genuine feelings with a clear narrative he wants to execute. Stay tuned for 2016 free agency.
In the meantime, Views from the 6 may not be here yet, but in a largely successful attempt to trace his journey to the fifth OVO Fest, Drake is staking out ground for the next leg.