Drake With Owl
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Like him or not, Drake is on a fast ascension to the top. The 26-year-old rapper took his career to new heights during his 4th annual OVO Fest, where he outdid himself last year by bringing an all-star lineup of surprise guests. Standing among the biggest names in rap at the Molson Amphitheatre, it’s safe to say that Drake has gotten the respect he deserves.

While this is one staple of October’s Very Own, the brand has picked up as its own label since signing a partnership deal with Warner Bros. In typical Drake fashion, he’s been calculated with every prospect rather than signing whoever is hot at the moment. This year, he’s been on somewhat of a signee spree, welcoming his first artist PartyNextDoor and singing/producing group Majid Jordan. Now, the Internet has been buzzing over talks of Cassie and Ma$e making the move to OVO.

Again, these are rumors, but it got us thinking about who would fit under Drake's relatively new label. Here are 10 artists we think that should sign on the dotted line.—Eric Diep, Dan Jackson, & Christina Kelly

The Weeknd

Drake introduced much of the world to the Weeknd and contributed to the track "The Zone" on the mysterious Canadian singer's second mixtape, Thursday, but the two haven't exactly seen eye to eye since. Afte hinting at disagreements for months, the pair seemed to make amends earlier this month when Champagne Papi posted a photo on Instagram of the two back in the studio together. You know what would be a great way to celebrate this reunion? Snatching The Weeknd away from Republic Records after the release of Kiss Land and bringing him on board to OVO.

Chilly Gonzales

The best labels have eclectic rosters that do more than just echo the taste of the imprint's figurehead. Signing a pianist and composer like Chilly Gonzales, who has worked with Drake in the past on "Marvin's Room" and other tracks, would be a good move for a label trying to establish itself as a home to adventurous music. Gonzales' Solo Piano II came out in 2012, so why not release a third part in the series on OVO? Also, maybe if they were on the same label we'd get to see Drake and Chilly do more monologues together.

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Jay Electronica

There's no beating around the bush with this one – an album from the New Orleans native is well overdue. After the late 2009 release of the Just Blaze produced singles “Exhibit A” and “Exhibit C”, it was clear that Jay's wordplay warranted him respect. Excitement ensued in the hip-hop community when he was signed to Jay-Z's Roc Nation label in November of 2010. With mention of Act II: Patents of Nobility (The Turn), which was to be his debut album under the Roc, and Act III: The Last Will & Testament of Timothy Elpadaro Thedford (The Prestige), to be his sophomore release, being completed, many looks to Electronica as a game-changer. However, for sparingly-known and variously-predicted reasons, neither album have been released to the public.

So What would Drake want to do with an artist like Jay Electronica? Two things. Firstly, Electronica has undeniable talent. As a master of wordplay himself, Drake would be smart of harness Jay's talent to build repertoire for his OVO label brand. Electronica, though not highly decorated, is a veteran to this game, having worked behind the scenes with long-respected names such as late and legendary producer J. Dilla, Yasiin Bey, Mos Def and Nas. Secondly, if marketed and branded correctly, Drake can provide the direction and means for Jay Electronica to not just finally drop an album, but drop an album that successfully displays Jay's talents and preserves his natural boom-bap sound while exposing him to a new, more mainstream demographic outside of the underground. Sounds like a win-win to us.

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Hit-Boy

Hit-Boy has come into his own as the newest producer who can spit a few bars too. Surprisingly, there hasn’t been an official collaboration with Drake yet. However, there are several photos of their studio sessions that hint it’s coming real soon. Hit’s got a signature sound—alluring synths and explosive drums—and is starting to become a compelling rapper that fans can relate to. Plus, he seems like an easy sell to adapt to the OVO sound. If his track record of scoring hits with Drizzy’s contemporaries is enough proof, then we might see a HS87 x OVO joint venture in the future.

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Jhené Aiko

The songbird, whose infectious falsetto has brought her notable collaborations with the likes of Black Hippy, J.Cole, Big Sean and more, has been in Drake's sight's for quite some time. The two were first associated when Drake decided to cameo on Aiko's “July” track, off her debut mixtape Sailing Souls, released in early 2011. Since then, not much was to be said about the brief partnership until earlier this month, when Drake took to Twitter to confirm that Aiko would indeed be on his upcoming and well-anticipated album Nothing Was The Same. Signing Jhene Aiko would be a predictable and well-played move by Drake for many reasons. Aside from the fact that her signature crooning would make her a befitting 'first lady' (think Teyana Taylor for G.O.O.D. Music, Ashanti for Murda Inc, etc.), her singing style is also in sync with Drake's characteristically expressive music. His style of production would also work well with Aiko's gentle vocal nuances.

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Key Wane

Currently, Key Wane is part of Big Sean’s extended Finally Famous roster. The 22-year-old producer was behind some of the biggest rap songs such as Meek Mill’s “Amen,” Sean’s “Guap” and Drizzy’s summer banger “All Me.” With OVO's in-house roster looking pretty promising—Boi-1da, Mike Zombie, T-Minus and 40—the beatmaker would be the perfect addition. Who wouldn’t want to see more Key Wane/Drake collaborations?

Sampha

Few are aware of the person behind the lulling, mesmerizing vocals behind one of Drakes most recent releases, “The Motion." Sampha is actually one half of the London indie pop duo SBTRKT, whose sound is most known in the western hemisphere for their alternative hip-hop/electronica 2011 release “Wildfire” with Little Dragon's Yukimi Nagano, which Drake later remixed with his own verse. It is clear that Drake kept in touch with the duo after the brief yet well-remembered remix, but is it a partnership that will reach such a height as the OVO label? We think it's pretty likely.

As Drake is doing with the talented vocalist James Fauntleroy, Sampha would be an outstanding vocalist for the label. Sampha's unorthodox crooning and indie-pop background with SBTRKT would surely diversify the OVO roster, expanding it's reach outside of the hip-hop demographic. Consequently, signing Sampha would be another indication of Drake's expansion of his own sound. As we've been seeing with his more recent releases, particularly “Hold On We're Going Home,” Drake seems to be testing the waters outside of his R&B/hip-hop sound and experimenting with the fusion of hip-hop and other alternative genres.

Nickelus F

Nickelus F a.k.a. Sweet Petey was one of Drizzy’s main influences when he started rapping. Over the course of his career span, the Virginia native has gained a reputation for his string of mixtapes such as Heathen, Thank You, and his most recent Vices. That tape featured the Jake One-produced collaboration “The Number 15,” which stood out for their chemistry and fluidness. Drizzy is all about giving back to those who show him love, so we wouldn’t be surprised if he signed one of his early supporters.

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Ma$e

Late '90s rap superstar Ma$e has made waves recently, hinting that he's ready to come back to music by signing either with Kanye West's G.O.O.D. Music team or Drake's OVO camp. Drake himself spoke on the matter this weekend, telling MTV News that he's had conversations with Mase about working together in the future. Will Kanye and Drake end up in a bidding war?


Cassie

In a recent Revolt TV clip, we saw Diddy and Ma$e behind the scenes at Drake’s OVO Fest. It was moment that made hip-hop history since they haven’t officially been together for a performance in nearly 9 years. Surprise guests such as Kanye West, Big Sean, 2 Chainz and more were celebrating with them, as well as Cassie who was seen hanging out with the crew during the afterparty.

Days after OVO Fest was over, rumors circulated that Cassie may have joined Drizzy and 40’s imprint. The source was an upcoming Mediabase newsletter, which stated the R&B songstress “now inked another deal with Drake and Noah “40″ Shebib’s OVO Sound, their first big signing.” She’s currently in a distribution partnership with Bad Boy/Interscope and that means OVO would be her second home.

Whether there's any truth to it, Cassie joining OVO would be a major win for Drake. Her RockaByeBaby mixtape marked a huge return into the R&B/hip-hop game because it was the first project since 2006's Cassie that really showcased her maturity. To see her finally get comfortable as an artist, it's the right moment to capitalize and build the OVO brand.