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Drake had a quiet 2019 but was just as influential as years past. He may not have released a ton of new music this year, mostly collaborations with the likes of Summer Walker, Chris Brown, Rick Ross and others, but he did earn his fourth Grammy Award, in addition to becoming the first solo artist to make 200 appearances on Billboard’s Hot 100. In February, the superstar entertainer re-released his third mixtape, So Far Gone, onto streaming services for the first time, commemorating its 10-year anniversary. Then in May, he kicked off his Wynn Nightlife residency in Las Vegas.

Outside of music is where Drake owned 2019. He brought two critically-acclaimed shows to television in HBO’s Euphoria and Netflix’s Top Boy, while Showtime ordered his Ready for War docuseries. His hometown team, the Toronto Raptors, renamed their practice facility the "OVO Athletic Centre" and then went on to win the Championship. His OVO fashion label collaborated with Dsquared2 and recently opened a flagship store in Tokyo. Drake even expanded his empire into the realms of cannabis and eSports. If 2019 was about growing his business portfolio, then 2020 should bring new music and hopefully a new album.