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The 29-year-old, who has been romantically linked with Rihanna, raved about the hit-maker after arriving on stage in his tuxedo with the award in his hands.
'She's someone I've been in love with since I was 22-years-old,' Drake admitted as he delivered a lengthy and glowing speech in honour of Rihanna immediately following her fourth performance during the MTV Video Music Awards.
Drake's appearance triggered speculation amongst fans that he was actually going to propose to Rihanna when he presented the award to her.
'She's one of my best friends in the world,' Drake added in his speech. 'All my adult life, I've looked up to her, even though she's younger than me.'
'She's a living, breathing legend in our industry, ladies and gentleman, the recipient of the Michael Jackson Vanguard Award for 2016, Rihanna.'
As Rihanna gave him a peck on the cheek, Drake continued to lean in to kiss her on the neck.
But the kiss didn't last very long, as he pulled away after several seconds just before Rihanna said several words to him.
'MTV, this is such an amazing night, it's such an amazing moment in my career,' Rihanna started off her speech. 'When I think about the Vanguard Award and receiving this tonight, all I could think of was my country. They're gonna be so proud, this is the first Vanguard to land anywhere close to my country,' she said.
'And so, you know my success, it started as my dream. But now my success is not my own. It's my family's, it's my fan's, it's my country's, it's the Caribbean as a whole, it's women, it's black women, so many people feel like their little piece is such a major part of this puzzle, and I have to thank you guys for supporting me over and over.
'Thank you to every director whose taken a chance on me, and a chance with my crazy ideas, there's just so much growth that has happened over the last eleven years, and I can't believe I'm receiving a Michael Jackson Video Vanguard Award at 28 years old.