Dionne Osborne is the vocal coach who started working with Drake during the Away from Home tour to promote So Far Gone and Thank Me Later in 2010. She's not to be confused with Drake's mom, though as Jezebel's recent interview with with Osborne's confirms, folks tend to mistake the middle-aged white woman chilling with OVO in V.I.P. for Sandi Graham all the time, when in fact, Dennis is the only other Graham outchea.
Among Osborne's earliest goals in her work with Drake was to keep him from sounding "like an uptight Jewish dude" in his live performances. In her interview with Jezebel, Osborne, who's professionally based in Atlanta, says she totally understands modern rappers' infatuation with singing. Drake, she says, is ideally a "singer who raps, not a rapper who sings":
I'd done my research. [After So Far Gone, he] was blowing up, so I was like, let me listen to this and figure out what people are loving about this kid. What I found in those recordings was that he has the most comfortable voice. It wasn't showy, and it had a very nice tone: it sounded so conversational. He wasn't singing at you, but singing to you. A lot of singers overdo it, try to bombast you, but Drake doesn't. And the average person can sing Drake's songs, and that's part of what they love.
Osborne goes on to share her abundance of insights into Drake's nightlife and drinking habits, which she tries to regulate by force-feeding Drake bottles of water, not unlike how your own mother fed you between the ages of zero and two years old:
The first three years, everyone thought I was his mom. Sandy is a cute Jewish woman who looks nothing like me, but you've been in the club, you know—if I'm older than everybody, and I'm in the VIP, I must be Drake's mom!
So he's standing there, his hand wrapped around the neck of this thousand-dollar champagne bottle. I pull it to me. I'm not a big drinker, I'm a total lightweight—I'm a daiquiri drinker, or margaritas, but champagne just knocks me out. So I don't know anything about it, don't know this one's so expensive. I'm like, "You don't think you're gonna drink this whole thing, do you honey? You can have a GLASS." He looks at me like I'm crazy! So I call over the management and tell them Drake needs water, and they bring me a whole case! There are more and more people crowding in here, I'm getting crowded to the back, so I start passing a bottle of water through the crowd. His bodyguards are all looking back at each other, like, "What is this?" And I'm just mouthing, "GIVE IT TO DRAKE."
Finally it gets to Drake, and the bodyguard just points right at me. Literally, Drake's shoulders go down six inches. Totally resigned. But, he drank the water. He got it!
Voss water in the V.I.P. is essentially Drake's version of #RossFit.
