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Kanye, Diddy and more: Hip-hop heavyweights surprise crowd at Drake’s OVO Fest

Drake is joined by The Weeknd as he performs at OVO Fest at the Molson Amphitheatre in Toronto, August 5, 2013

J.P. MOCZULSKI/The Globe and Mail

"Wait till I get my money right / Then you can't tell me nothing, right?" The lines are from Kanye West's defiant 2007 hit Can't Tell Me Nothing , but they were more than apt on Monday night at Toronto's Molson Amphitheatre, where the fourth annual edition of Drake's OVO Fest left even the most disgruntled hip-hop fan satisfied.

And disgruntled they were, at least initially, as a poorly organized box office resulted in waits as long as two hours for fans looking to change their two-day tickets to single-day ones following R&B crooner Frank Ocean's cancellation due to throat issues last week. The ticket backup meant hundreds of fans were left waiting outside the gates to get paperwork sorted out, as British singer-producer James Blake (a holdover from the cancelled Day 1) and Washington rapper Wale, respectively, warmed up the modest, chatty crowd inside.

But the ticketing issue was the only evidence of growing pains at the increasingly popular OVO Fest. In its first three years, OVO (which stands for October's Very Own and acts as a defining moniker for the October-born rapper's group of friends/collaborators) has garnered a reputation for showcasing some of Drake's most famous friends by way of surprise appearances, and Monday evening's show more than delivered in that regard.

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The former Degrassi star took the blue-lit stage shortly after 8:30 p.m. to the strains of Headlines , but he wasn't alone for long, as enigmatic R&B up-and-comer The Weeknd joined him for Crew Love , and Detroit fast-talker Big Sean followed, both to big applause from the sold-out crowd. Drake's own set leaned heavily on his new material – his third full-length, titled Nothing Was The Same , is expected in September – but that didn't mean there wasn't room for nostalgia.

And there was plenty of that, starting with an appearance by R&B icons TLC, whom Drake introduced to the stage to sing the hook for the new track I Get Lonely Too . That loneliness was surely alleviated when TLC's Chilli smothered him with a bear hug after the group's brief, triumphant set, which included Waterfalls and No Scrubs (each featuring recorded raps by founding group member Lisa "Left Eye" Lopes, who died in a car crash in 2002).

After TLC, Drake brought out his "twin" J. Cole, who performed two tracks of his own before being joined by elaborately coiffed crooner Miguel, who stayed on to perform his own hit Adorn .

Following a chipper drop-by from New Yorker French Montana, a wistful Drake reminisced about his uncle taking him to a show at the venue as a kid, which segued into a typically bombastic appearance by Diddy. Clad in a loudly patterned T-shirt, the Artist Formerly Known As Sean Combs received a hysterical welcome, which was only amplified when he was joined by his former protegé Mase on classic tracks like Feel So Good . After the twosome ambled off, Drake once again tipped his hat to the new school with a boisterous A$AP Rocky, who performed the by then highly appropriate Wild for the Night.

Far from playing second fiddle to his famous friends, Drake enjoyed baiting the crowd as he danced, quipped and teased them about who else could be waiting in the wings.

One-upping Diddy, who, despite his somewhat cheesy demeanour remains one of hip-hop's biggest names, was no small feat, but Drake got it done. Kanye West's appearance had been perhaps the biggest, loudest rumour leading up to the show, but the crowd's shock was still palpable as the Louis Vuitton Don actually took the stage. The Chicago-born rapper performed New Slaves, All of the Lights and Can't Tell Me Nothing, which he stopped to pay his respects to the evening's host, something that all names big and small did Monday night.

The night's final guest slot went to Drake's mentor, Lil Wayne, who grinned and rapped his way through HYFR, The Motto and Love Me , before leaving the king of the night to end things off, which he did, of course, by shouting out Toronto yet again. "No matter where you are, every time you hear my voice," Drake told the ecstatic crowd before saying his final goodbye, "you're hearing a piece of this city."

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