Drake’s complicated relationship with the Grammy Awards
Like many young artists, Drake always dreamed of winning a Grammy. It was the age-old tale of stepping up on stage and thanking those most important to him, but he soon realised he wouldn’t have his way in the music industry. By as early as 2011, with only his Thank Me Later and Take Care albums out in the world, he had a different perspective on the Grammy Awards.
Following the release of his second album, Drizzy had been nominated for six Grammys but failed to win in all of the categories. The Toronto rapper was particularly disappointed that Jay-Z beat him to the ‘Best Rap Solo Performance’ award at the 52nd Annual Grammy Awards in 2010. Hov picked up the win for ‘D.O.A. (Death of Auto-Tune)’, taken from his The Blueprint 3 album, when Drake felt ‘Best I Ever Had’ deserved the prize.
“I’ve always been fascinated with the Grammys, so I don’t mean disrespect when I say this, but I’ve kind of given up on them,” he told Billboard in 2011. “If I ever get one, or when I get one, I’ll be ecstatic, because that’s a recurring dream I’ve had since I was a kid: That my mother’s still alive and that I’m onstage accepting a Grammy, and I get to thank her on that stage.
“But it’s tough. They can never really break their mould. Forget last year, because when I read up on the young lady that won, she did some incredible things. And if we’re talking numbers, nobody’s really achieved what Justin Bieber achieved as far as the earnings and just worldwide. He deserved it as well. But the one that really got to me was when I lost to ‘D.O.A.’ for ‘Best I Ever Had’.”
He continued, “That one to me was, like, really? Not to say that Jay-Z isn’t the most incredible rapper and that ‘D.O.A.’ wasn’t a good song. I just felt like they had an option to give me a Grammy for a mixtape, and they just didn’t do it. Because it goes against the grain of everything that is traditional.”
As of 2025, Drake has won a total of five Grammys. His wins came for his Take Care album and the songs ‘Hotline Bling’, ‘God’s Plan’, and ‘Wait for U’. After losing in all four categories in 2024, he wrote on Instagram, “All you incredible artists remember this show isn’t the facts — it’s just the opinion of a group of people whose names are kept a secret. Literally. You can Google it. Congrats to anybody winning anything for hip-hop, but this show doesn’t dictate shit in our world.”
Not only has Drake called them out in interviews and on social media, he also took the opportunity during his acceptance speech in 2019. “We play in an opinion-based sport, not a factual-based sport,” he said on stage. “It is not the NBA. This is a business where sometimes it is up to a bunch of people that might not understand what a mixed race kid from Canada has to say or a brother from Houston right there, my brother Travis [Scott].”
He continued, “You’ve already won if you have people who are singing your songs word for word, if you are a hero in your hometown. If there is people who have regular jobs who are coming out in the rain, in the snow, spending their hard-earned money to buy tickets to come to your shows, you don’t need this right here. I promise you, you already won.”
Drizzy boycotted the Grammys in 2022, submitting then withdrawing Certified Lover Boy for ‘Best Rap Album’ and ‘Way 2 Sexy’ for ‘Best Rap Performance’. Rubbing more salt into the wound is the fact that Kendrick Lamar won five Grammy Awards for his Drake diss track ‘Not Like Us‘ this year. He picked up ‘Song of the Year’, ‘Record of the Year’, ‘Best Rap Song’, ‘Best Music Video’, and ‘Best Rap Performance’ for a track that accused Drizzy of paedophilia and sexual misconduct. That’s enough to turn anyone against them.