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OVO Fest 2016 predictions: which surprise guests will Drake bring onstage?

Melody Lau

For seven years now, Toronto rapper Drake has treated his city to an annual celebration of rap, hip-hop and R&B with his blowout event, OVO Fest. In addition to performing, Drake has brought along some amazing guests, including Outkast, the Weeknd, Big Sean and J. Cole. This year, performers include Snoop Dogg, Wiz Khalifa, Beenieman and Machel Montano.

What’s even more exciting though are the guests that don’t appear on the bill – the surprise guests. Since its launch in 2010, Drake has consistently dazzled fans with an impressive list of surprise appearances from Kanye West and Jay Z to Stevie Wonder and TLC. Whether they’re collaborators or influences of Drake’s, he has always put together a list of artists that is hard to predict. That, of course, doesn’t stop people from theorizing every year, which is what we’re about to do. Below is a list of who we think may show up to this year’s OVO Fest.

Who do you want to see show up? Share your thoughts and predictions with us on Twitter at @CBCMusic!

Gucci Mane

Last week, Drake showed up to Gucci Mane’s triumphant homecoming show in Atlanta. Drake even shows up on Mane’s new album Everybody Looking, so maybe the newly released rapper will return the favour by appearing at Drake’s hometown gig.

Chances of showing up: 10-1

Editor's note: strong language warning.

French Montana

Drake recently teamed up with New York rapper French Montana on the track “No Shopping,” and while he does have a tour later this summer, Montana appears to be free this coming weekend.

Chances of showing up: 4-1

Editor's note: strong language warning.

DJ Khaled

DJ Khaled’s upcoming album Major Key features a long list of guests, including Drake on the track “For Free.” With the song climbing up the charts right now, OVO Fest would be a prime spot for the two to get together and perform it live.

Chances of showing up: 7-3

Editor's note: strong language warning.


Toronto artist and OVO Sound signee PartyNextDoor has shown up to multiple OVO Fests in the past and with a new album coming out next month (which will include the Drake collaboration, “Come and See”), it’s almost certain that both PartyNextDoor and Drake will take the opportunity to promote the release.

Chances of showing up: 3-2

Editor's note: strong language warning.

Majid Jordan

Another OVO Sound artist who has made an appearance at OVO Fest before, Majid Jordan might show up to perform some tracks from their self-titled debut which came out earlier this year. They could also team up with Drake to perform the Nothing Was the Same hit single, “Hold On, We’re Going Home.” While Majid Jordan have plans to hit the road in the fall, it looks like their summer is open right now, leaving plenty of room and time to trek down to the Air Canada Centre.

Chances of showing up: 3-1


Chicago R&B artist Jeremih was one of the many guests on Drake’s new album Views, performing on a track called “With You” alongside PartyNextDoor. To further his OVO connections, Jeremih and PartyNextDoor announced a collaborative album called Late Night Party (as part of Jeremih’s Late Night series of releases) last month so perhaps they might preview some tracks this weekend. Jeremih is scheduled to perform a show in Beverly Hills, Calif. on July 30, but with no tour dates on the following days, it leaves him plenty of time to head north to Toronto.

Chances of showing up: 5-2


Drake has guested on two YG songs, 2014’s “Who Do You Love?” and this year’s “Why You Always Hatin?” off of YG’s latest album, Still Brazy. YG is currently on tour with G-Eazy, Logic and Yo Gotti but isn’t performing on Aug. 1. On July 31, he will be in Cincinnati, OH which isn’t terribly far from Toronto.

Chances of showing up: 6-2

Editor's note: strong language warning.

Cypress Hill

While the iconic hip hop group has no ties to Drake, Drizzy is known to bring some old school talent to OVO Fest (Lauryn Hill, TLC, Diddy and Mase). Cypress Hill will be performing at this year’s Osheaga festival in Montreal so a trip to Toronto is plausible.

Chances of showing up: 15-1

Editor's note: strong language warning.

Vince Staples

Also performing at Osheaga is Long Beach, Calif. rapper Vince Staples. Like Cypress Hill, Staples doesn’t have any connections to Drake but it would be a nice surprise to see Drake bring in one of rap’s most exciting young voices right now.

Chances of showing up: 35-1

Editor's note: strong language warning.


Frequent collaborator and rumoured girlfriend Rihanna has a tiny gap in her tour schedule, with no performances scheduled on July 31 or Aug. 1. But the pop star is in Europe so that might make travelling a little more complicated, though not impossible.

Chances of showing up: 30-1


Queen Bey is also currently on tour in Europe but is also free on Aug. 1. Will she hop on a plane from Belgium to Toronto?

Chances of showing up: 100-1

Jay Z

Beyoncé’s husband, on the other hand, is not on tour and could show up, pending there’s no bad blood between the two over Jay Z’s exclusion from Views due to Drake’s allegiance to Apple Music (Jay Z and Tidal’s main competitor).

Chances of showing up: 60-1

Missy Elliott

With a new album on the way (or so we hope), Missy Elliott has been making more appearances lately, from this year’s VH1 Hip Hop Honors to Michelle Obama’s Carpool Karaoke segment on the Late Late Show With James Corden. Elliott and Drake have never really teamed up on anything but Drake has long shown love for one of Elliott’s closest friends, Aaliyah, who died in 2001.

Chances of showing up: 35-1

Editor's note: strong language warning.

Frank Ocean

In 2013, R&B star Frank Ocean was slated to perform the first of a two-day OVO Fest, but later canceled due to a torn vocal cord. Many have speculated that Ocean will return in the future for a make-up set but he has yet to make a proper appearance at the festival. With a new album coming out soon, could this be the year Ocean finally shows up?

Chances of showing up: 25-1

Joe Budden

Yes, the two are in the middle of a vicious feud, but Drake did say this at his Dallas show: "I should have brought Joe Budden up here and let him do 'Pump It Up' one time tonight." Maybe he'll actually let him do that at OVO Fest!

Chances of showing up: 1,000,000-1