Drake Welcomes Usher, 50 Cent, Lauryn Hill And Many More To Fifth Annual OVO Fest

Rich Arden / ESPN Images

Drake during the 2014 ESPYS on July 16 at the Nokia Theatre in Los Angeles, CA. 

Drake’s OVO Festival is like hip-hop Christmas in Toronto – you anticipate it every year but you never know what you’re gonna get.

Prior years have brought surprise cameos from the likes of Rick Ross, Nicki Minaj and Snoop Dogg, or Diddy, Mase, Kanye West and Lil Wayne, and this year’s finale Monday night (Aug. 4) only added to the epic lineups that came before it. From unannounced opener Lauryn Hill all the way to an 11th-hour visit from 50 Cent, with stops from Trey Songz, J. Cole, Tinashe, OB, YG, PARTYNEXTDOOR, DJ Khaled, Majid Jordan and Usher along the way, Year 5 of OVO was a nearly three-hour celebration of Drake’s “journey” from Toronto ruling the hip-hop world and the many artists who helped put him on the map, and vice versa. “The way I designed tonight is if you’ve been a fan of music, or a fan of Drake, I'm gonna take you back tonight.”

Because there were too many highlights to neatly summarize in one recap, let’s take a look at the minute-by-minute rundown of the night’s program. 

OutKast, YG Bring Few Surprises To First Night of Drake's Two-Day OVO Fest 

8:00 p.m. After a brief warm-up set from Jhene Aiko (who naturally sang her hook on Drake’s “From Time”), anxious fans start placing bets on who might show up tonight. Optimists are holding out for Rihanna, Beyonce or Jay Z, realists know that J. Cole and PARTYNEXTDOOR will be there for sure, and locals heard tell of Lauryn Hill and Usher being in town for rehearsals. Then there’s the absurdists holding out for a Justin Bieber cameo -- which, given the Usher rumors and the Canadian backdrop, aren’t entirely out there.

8:34 p.m. Two guitarists take the stage and start playing a funky dancehall groove. Three backup singers materialize shortly thereafter. Soon enough, a voice booms, “Get your hands together, Ms. Lauryn Hiiiilll!” OVO has officially begun.

8:37 p.m. Hill kicks things off with a reggaefied take on “Killing Me Softly,” which has doubled as the opener on her recent club gigs in New York and other markets. The new arrangement is so unique from her mid-90s cover that several fans start to ponder “Who is this?” out loud. 

8:43 p.m. “Ooh la la la. It’s the way that we rock when we’re doing our thang.” In case there was any doubt who was onstage, Hill drops a little “Fu-gee-la” to refresh the crowd. A more faithful take on “Ready Or Not” soon follows, and the young-skewing crowd is sufficiently hyped.

8:49 p.m. Just as “Doo Wop (That Thing)” is bringing the sunshine to the sunset backdrop, Drake shows up mid-song to pay his respects to Ms. Hill, bowing in praise and spitting a few appropriate bars from “Draft Day” (“five years later how am I the man still”). When a hip-hop legend opens your show, you know it’s going to be an epic night. 

8:55 p.m. “Y’all ready to get this shit started?” Drake drops a one-two with “We Made It” and “The Language” just to make sure.

9:01 p.m. Drake thanks “the greatest city in the world” for helping raise him and being able to host a concert that he’s been putting on its honor. Plus, “I gotta hug my mom before I do this show because it’s the fifth year…” Soon, Sandi Graham is rolled out onstage in a wheelchair, and confusedly repeats the question her son asks her rather than answering it: “Is it time to go home?” 

9:05 p.m. “Tonight’s not about one more song you heard 1 million motherfuckin’ times,” Drake says. “Tonight is about performing the songs I always wanted to do but never really got to.” And with that, he begins a chronological trip down Drake Lane, beginning with breakout mixtape “So Far Gone.” The title track and “Sooner Than Later” are tossed out, with the next surprise guest on deck.

9:07 p.m. “This next person was the first person to ever embrace my music to ever do a feature with me,” Drake says before bringing out Trey Songz to perform “Successful” and Songz’s current hit “Na Na” (no sign of Lauryn Hill, however, on the Fugees-referencing chorus). “I promise you my career as a human being would be nowhere without this guy,” Drake continues of Songz, who appeared to be going out of his way to smooth over any beef from his dis lyric on 2013’s “From Time." “We come a long way in five, six years.” 

9:14 p.m. Now it’s time to enter the “Thank Me Later” era, and it’s nearly all deep-cuts affair, beginning with snippets of “Karaoke” and “Fireworks” before blazing into “Show Me A Good Time” and fan favorite “Up All Night,” with Drake handing the mic to the crowd for the first half of Nicki’s verse. We get the first verse of “Over” before it’s time for the next guest to say "hi."

9:21 p.m. “At this point in my life,” Drake says of the 2010 period, “I’m getting calls from the greats to write songs, be part of things, and while I’m doing that there’s this other guy who can really rap, he’s from North Carolina. And instead of becoming enemies, we become great friends.” J. Cole makes what has quickly become an annual visit to OVO, reprising his 2013 appearance with “Can’t Get Enough” and “Power Trip.”

9:25 p.m. Drake uses the occasion with J. Cole to kill beef with another rapper, Kendrick Lamar, who didn’t make the trip to Toronto but whose presence Drake nevertheless wanted to be felt. “Man, this rap game can get fucked up sometimes, they try to make stuff happen,” Drake says. “I wanna shout out my man Kendrick Lamar -- he was on my album, I was on his, we were touring together. He’s one of the hardest n****s out there. He should be standing right here.”

9:27 p.m. No signs of Chantal Kreviazuk or The Weeknd tonight, but their hooks from “Over My Dead Body” and “Crew Love,” respectively, are getting a loud performance from the Molson Amphitheatre. 

9:35 p.m. “I got one request up here,” Drake says, scanning the audience. “I got to go out there and see the people. It takes a lot for you to spend your hard earned money and come out here.” And with that, he steps on his mic stand, the mic stand ascends from the stage, and Drake begins singing “Marvin’s Room” while floating above the crowd, saying "hi" to friends like Jhene Aiko and shouting out random fans in the process. “There’s not too many rappers who would do this shit, by the way,” he adds upon descension back to the stage. “It's like me and One Direction or some shit.”

9:42 p.m. A bright red “6” logo flashes on the screen as Drake begins to spit verses from recent hype track “Days In The East.” It would appear the Toronto section of the set has arrived. To further affirm that assumption, PARTYNEXTDOOR shows up, performing “West District,” “Persian Rugs” and Drake collab “Recognize.”

9:56 p.m. PARTY’s mellow vibes slow the energy level a bit, but Drake already has a party trick up his sleeve. “At one point I bought this condo in Miami, like I lived in Toronto my whole life, I needed to spend five, six months in Miami,” he explain. “Some of the craziest times in my life are because of this crazy motherfucker.” DJ Khaled appears to the strains of “All I Do Is Win,” with Drake jumping on the mic for “No New Friends” and “I’m On One.” 

10:02 p.m. Drake revisits his famous courtside lint-roller moment from earlier this year in a GIF that accompanies his triumphant performance of “All Me,” deftly tackling (and nailing) the 2 Chainz verse on his own. 

10:05 p.m. Tinashe appears to perform current hit “2 On,” which Drake and OVO Sound rapper OB jump on to add their “Thotful” verses. As if to keep the DJ Mustard sound flowing, YG shows up next for a little “Who Do You Love?”

10:09 p.m. “I'm so honored to have this particular piece of the show,” says Drake. “This is probably gonna be one of the best moments in OVO history so make some mothafuckin’ noise.” When Usher emerges from sidestage, OVO reaches its own kind of “Climax,” even though there’s still an hour left in the program.

10:20 p.m. Usher sustains the shrieks that met his arrival with full-length run-throughs of “Confessions Pt. II,” “Lovers And Friends” and “U Don’t Have To Call,” before gauging whether he can indulge the crowd in “my new shit that I’m cooking with.” Though the crowd certainly seems to recognize currently single “Good Kisser,” it gets the weakest reception of his short set.

10:31 p.m. Drake reveals he’ll be appearing on Usher’s upcoming album, expected this fall, and asks his friend to show off his signature slide dance. “From ‘My Way’ to ‘8701,’ I used to swing a chain around my neck,” Drake recalls, “I had the Sean Johns on, I had the roller-skating shoes on. Can we just slide walk for a second, you still got it?”

10:33 p.m. “Should we find out the last chapter of the story or what? Because I promise you it’s not time to get tired yet.” “Wu Tang Forever” and “Own It” set a downtempo vibe, but before you know, “Hold On, We’re Going Home” has been fired up. And with one of the first public performances from Majid Jordan’s lead singer Majid al Maskati, it becomes an epic eight-minute funk-turned slow jam, with Drake and Majid trading vocal runs to make the ladies swoon. Perhaps because he’s outsinging his label boss, or maybe because few in the crowd have seen what he looks like, Majid appears to be winning over the crowd. “All these lookin’ at me, they confused. They should be talkin’ to the girl next to them,” he says.

10:45 p.m. “Alright we slowed down too much. I don't wanna hear any more of that soft shit tonight.” The snare from “Started From The Bottom” kicks in, while the night’s final guest cues up.

10:48 p.m. “Now look, I told you I wanted to bring people to you that maybe you ain’t never seen before.” And with that, 50 Cent and his G Unit crew members Lloyd Banks and Tony Yayo appeared, ripping into “Gangsta,” “Smoke” (featuring another cameo from Trey Songz), “I Get Money,” “Don’t Worry Bout It” and a rousing “In Da Club” to bring things home. All the slow jams paid off, because the 16,000-plus crowd saved their lungs for 50’s appearance.

10:57 p.m. OVO Year 5 hasn’t quite ended yet, but Drake is already taking requests for Year 6. “Who you want me to bring next year?” Eminem, Jay Z and Nicki’s names can be heard. “Lemme work on some things,” he teases.”

11:10 p.m. The Molson technically has an 11 o’clock curfew, but Drake is blissfully ignoring it by playing the majority of “Trophies,” “Believe Me” and current hit “0 to 100” to bring things to a proper coda. But before he leaves the stage, he asks the crowd one last favor: to give his friend Kevin Durant, of the NBA’s Oklahoma City Thunder, a taste of what could happen should he ever decide to come play for the Raptors. The crowd officially out-screams themselves, proving that Drake has far more pull in Toronto than even 50 Cent. 

11:15 p.m. And his next, as-yet-unrecorded album “Views From The 6” will make sure he reps his city even harder. “I’ma let you know I’m about to go on this tour, and I’m about to come home and make the best I ever made for y’all,” Drake teases, before finally calling it a night. Rob Ford may technically still be the mayor of Toronto, but Drizzy owned his city for three blissful hours. 

Drake Set List:

"Draft Day" w/ Lauryn Hill
"We Made It"
"The Language"
"So Far Gone"
"Sooner Than Later"
"Successful" with Trey Songz
"Na Na" w/ Trey Songz
"Show Me a Good Time"
"The Resistance"
"Up All Night"
"Can’t Get Enough" with J. Cole
"Power Trip with J. Cole"
"Crew Love"
"The Motto"
"Marvin’s Room"
"Days in the East"
"West District" with PARTYNEXTDOOR
"Persian Rugs" with PARTYNEXTDOOR
"Recognize" with PARTYNEXTDOOR
"All I Do is Win" with DJ Khaled
"I’m on One" with DJ Khaled
"No New Friends" with DJ Khaled
"All Me"
"2 On" with Tinashe
"Thotful" with OB
"Who Do You Love?" with YG
"Climax" with Usher
"Confessions Part 2" with Usher
"Lovers and Friends" with Usher
"U Don’t Have to Call" with Usher
"Good Kisser" with Usher
"Wu-Tang Forever"
"Own It"
"Hold On We’re Going Home" with Majid Jordan
"Started From the Bottom"
"Gangsta" with G Unit
"Smoke" with G Unit and Trey Songz
"I Get Money" with G Unit
"In Da Club" with G Unit
"Believe Me"
"Worst Behavior"
"0 to 100"