TORONTO — In an age of spoiler alerts and album leaks and too much information, true surprises are harder to find than love, more difficult to schedule than memories.
But once a year at Caribana, under a Greek-inspired amphitheatre overlooking Lake Ontario, a half-white, half-black Jewish Santa Claus makes a list of surprise guests he’d like to bring out, checks it twice, and—this time with an assist via $300,000 of government grant money—manages to genuinely shock us with music.
Drake’s past OVO Fests have brought his city cameos from Jay-Z, Eminem, Kanye West, Lil Wayne, Puff Daddy and Ma$e, Stevie Wonder, Snoop Dogg and Nas. So, what gifts would Drake pull from his sleeve for the fifth day of Christmas?
1. Jhene Aiko blessed early arrivals with a mellow, 25-minute warm-up, busting out a sweet, unexpected cover of 2Pac’s 1993 demand for better treatment of women, “Keep Ya Head Up.” After a rainy afternoon, the skies had cleared just in time for the outdoor show. Walking casually offstage, Aiko pointed out the rainbow in background. “Look,” she instructed. “It’s beautiful.”
2. Unlike the first four OVOs, the first star to take the stage for the main event was not Drake, but rather Lauryn Hill. Supported by a trio of backup singers, Ms. Hill ran through her biggest tunes from The Miseducation of Lauryn Hill and The Score at a jacked-up pace: “Killing Me Softly,” “Lost Ones,” “Fu-Gee-La” and “Ready or Not.” The queen then brought the evening’s host onstage as “Doo Wop (That Thing)” segued into Drake’s Hill-sampling “Draft Day.” Ladies first.
3. After hyping the crowd with “We Made It” and “The Language,” the pride of the Six brought out his wheelchair-bound mom and gave her a hug as she fought back tears. A clumsy but endearing moment followed as Sandi Graham fumbled her attempt to hype the crowd at her son’s encouragement. Drake laughed it off: “We’ll work that out in rehearsal,” he quipped.
4. Bompton’s YG, decked out in a throwback Raptors jersey, stormed onstage to perform his “Who Do You Love?” joint with Drake. YG delivered a full set the night prior, opening up for OutKast on the first evening of the festival. Dude was chuffed to have made it across the border, saying, “I got strikes and felonies and all that shit.”
5. Never be as big as Trey Songz? Boy, was she wrong. Drake showered praise on Trey Songz, pointing out the R&B star was the first American artist to work with him, before the two knocked out “Successful”—a tune that holds up better than any other from Drizzy’s early catalogue—and Songz rocked his current radio smash, “Na Na.”
6. Playing a continuous loop of the clip of Drake lint-rolling his trousers during the Raptors-Nets playoff series throughout his performance of “All Me” was a stroke of self-deprecating genius. (Drizzy’s rhymed the absent 2 Chainz and Big Sean’s verses himself.)
7. “If the owner of the Molson Amphitheatre is here, I should just buy it, because I already own it,” Drake joked. Then he mounted a circular platform attached to mic stand. The apparatus elevated and hovered the MC over the 100 and 200 levels of the screaming fans, most capturing the moment on their smartphones as Drizzy performed “Marvin’s Room” and pointed out specific fans in the crowd (“I see you with the OVO hat!”), a cloying bit he cribbed from Jay-Z.
8. It was a nice touch that Drake brought out DJ Khaled, with whom he recorded a pair of monsters—“I’m On One” and “No New Friends”—but considering Khaled neither rhymed nor DJ’d, and knowing past OVOs have featured “I’m On One” cohorts Rick Ross and Lil Wayne, the cameo was a little underwhelming.
9. Better was the drop-in by J. Cole, whom Drake referred to as “my twin brother.” A regular performer in the city, Cole is adored in Toronto. So much so, the screams when he walked onstage were probably louder than for Usher, a guy with a diamond album.
10. Ah, yes, Usher. Drake credited the man who actually changed Justin Bieber’s life for changing his own as well—and those of everyone in the venue. Our affable host may have laid the hyperbole on a little thick, but Usher’s lengthy set, which included “Climax” and “Confessions,” appealed to the ladies. We learned that Drake will appear on Ushers new LP, Everything You Can Imagine. And in an off-script moment, Drake challenged Usher to do his “side waddle,” then demonstrated the vintage Usher dance. The artist more hilariously known as “Ursher” then asked for a beat and slid circles around the stage MJ-style. It was the kind of lighthearted, pure fun moment the show could have used a few more of, as the festival may be starting to creak slightly under the burden of high expectations.
11. Drake made a special point to shout-out peer Kendrick Lamar, a “king” in the game. “He should be standing right here,” Drake said, mentioning the two have recorded and toured together. It was a nice rumour-squashing gesture after Kendrick’s cutthroat “Control” verse (and his own snub at J. Cole’s recent LA tour stop), but it would’ve carried soooo much more weight had he been able to bring Lamar out for the show. (See: Kanye West, 2013.)
12. The appearances by lesser-known OVO Sound artists Majid Jordan, OB O’Brien and PartyNextDoor (who was granted a good half-dozen songs) showed crew love, but the up-and-coming artists may have been better served by getting proper billing and performing as opening acts. No doubt PND can sing, but next to an act like Usher, his still-developing stage presence pales. The down-tempo tunes also lulled a decidedly party-revved crowd into impatience. “Bring some rappers out!” demanded one boisterous head, speaking for many.
13. And so Drake obliged. After kicking away the clouds of smoke that set the mood for his Billy Oceanesque “Hold On, We’re Going Home,” it was as if Drake sensed the restlessness. “Enough soft shit,” he said.
14. “Started from the Bottom” bled into the best surprise of the night—50 Cent and G Unit compadres Lloyd Banks and Tony Yayo storming the dais to “What Up Gangsta.” Banks got off “Beamer Benz or Bentley,” and Trey Songz returned to perform “Smoke” with 50. “I Get Money” and, of course, “In Da Club” moved the crowd to rhyme-along mode that Drake carried through with new bangers “Trophies” and “0 to 100.”
15. NBA MVP Kevin Durant walked around general admission and was flocked by fans—tough to show up incognito when you stand six-foot-nine—until someone, mercifully, found him a spot in the VIP backstage. The Raptors’ global ambassador attempted to recruit when he asked the T.O. crowd the kind of reception KD would get if he played for the Raps. Naturally, the fans went berserk. Again. —Luke Fox