What was his range when you started and what is it now?

Hmm. Well, it's been so long. He was basically a baritone. I don't remember exactly how high he could go in his tenor voice, maybe up to a middle D? We've probably stretched him up to a G#, and he's gained his falsetto range, probably a whole other octave. I love that, I think a guy's falsetto is the coolest thing in the world: it's such a different timbre and sound. He's really just started using it, but I'm like, "Sing Usher's 'Climax'! Work on it!" He laughed at me and was like, "Oh my god, Didi, CLIMAX?! I can't—"

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If Drake covered "Climax"… I don't even know…

He's not afraid to experiment even on tour. He's pretty brave. He really has brass balls. I don't know how anyone can really make fun of Drake, because he makes more fun of himself than anyone else. He'll do whatever. When he hosted Saturday Night Live and did the skit as the Disney tour guide with the shorts all the way to his crotch—I just died! I remembered this moment on tour when I looked at him and told him, "Drake you have very pretty legs." He was like, no, I don't. I'm like, "Yeah you do! No girl has ever told you have pretty legs?" He goes, no.

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And there he was on SNL in those short, short, shorts! He probably encouraged the costume girl, "Go shorter with the shorts, you got to go shorter with the shorts." All just to make the scene even funnier!

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It's such a personal thing to be a vocal coach. You are helping people not just technically but in terms of emotional expression. I'm wondering what that's like with Drake, who is really emotional in his work.

Isn't that what being an artist about is—being vulnerable? Letting down those guards. I get so tickled. I just love crowd watching. You get 12-year-old white boys, African-American couples in their fifties, and then Indian college dudes! The span of people that relate to him is because of his willingness to be vulnerable. He understands the female psyche too, like no other rapper.

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Drake and I talk a lot about lyrics, too. Part of being a coach is trying to understand the whole person, their whole well-being, what they're about. What is it that he stands for? And I think Drake is true to that, and he's also honest about failures and failings and misgivings. That's what I like about his writing. Rap is an arrogant art form. It's, "I am more, I shine brighter, I have more." Drake is willing to have all of that and also say, "I haven't called my grandmother in two weeks." He's willing to talk about the difference between what society, media and culture wants us to be, and what we actually are. That's what a lot of twentysomethings fight with, I think. And I'm speaking as a fan, too. I'm 46, and this is what I see: people with his words just stamped on their lives.

Drake also seems willing to get silly.

Yeah, he loves to make people happy, he loves to make people laugh. He is an extremely naturally funny person—he's very smart, he's very witty, and very goofy. I always laugh, thinking, "Drake, if people could see you offstage, that street cred would just be—"

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I think that's part of his image already, though.

Yeah. That is the spirit of who he is. I told him, "Drake, good thing you're not trying to be this tough, hood guy. You had a bar mitzvah, for god's sake." I think he's become a better man for embracing every aspect of who he is. What you see is really what you get with him.

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I'm still thinking about how you have a mic to his in-ears. Do you ever get tempted to prank him?

Oh yeah! But I try to be careful. The last tour when we were in Europe, Drake wanted to speak some of the languages of the countries we were hitting. I've sung in German, Latin, and French, so I figured I could help him. So I started finding somebody in every place who could give me five phrases spelled out phonetically. I'd have them record it, and then Drake and I would go over it. Then I'd feed the words to him through the in-ears live. He is so good, he could be a newscaster. The guys in the band were like, "There's no way he can say all the things you just told them." But he did it, every time, and the crowds just went wild.

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Coolest tour stop?

I'm a big lover of history, so places like Radio City Music Hall, the Hollywood Bowl, the Chicago Theater, I'm always like, "My God, Drake, will you just look at the people who have been here?" Frank Sinatra, Liza Minnelli, everybody who was somebody.

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One time we started a tour in Düsseldorf, Germany—I can't remember the name of the facility right now, but it's where Hitler used to hold his youth rallies. The original balconies are still there, and the second balcony on the right was literally where Hitler stood, and the Allies dropped the bomb straight through the roof, and the bomb did not explode.

I looked at Drake and was like, "You, as a black Jewish man are standing on this stage right now." I was like, how cool is this—it's the ultimate finger to everything Hitler stood for. And Drake gets it. He's somebody that wants to make his mark.

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What's his favorite tour snack?

He's good now—he eats a lot of fruit, chicken and vegetables. He's got bananas and apples and grapes in his dressing room. And he's always drinking water, which is really good, because I've never seen anyone who is not a full-blown athlete sweat like that. He looks like he's showering on stage, he's shorted out microphones, let me tell you.

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What do you guys fight about?

Oh, more disagree than fight. But probably alcohol. He's an adult, and he may come in and say, "Didi, we drank too much last night." He generally steps away from all smoking. But probably in four years, we've only had two real times we've disagreed, and they weren't really arguments, it was me getting upset with him for spreading himself too thin. I keep saying, "You're the person that could get hurt here. You're the person that's going to walk on stage not being effective, and before you leave the building it will be on YouTube, and it'll be there FOREVER."

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I'm sure he gets frustrated with me more often than he shows it. I'm always like, "Drake, you don't have time to get your hair cut right now!" And he's like, "DIDI!" He's conscious about the way his hair looks. But then I'm over there, like Jiminy Cricket. The conscience.

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What is you on your worst behavior?

I'm pretty lame. Worst behavior for me, because I've been on a diet, would probably be eating an entire box of Krispy Kreme donuts in one sitting. I'm not a hell raiser, I was always that careful kid. I'm probably living vicariously through these rappers. If I drink I just fall asleep.

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Maybe it's driving like an idiot. I'm pretty aggressive in my car. It's a good thing there are no weapons on cars, otherwise I'd pull a Transformers!

Would you say that you subscribe to a YOLO philosophy in life?

Oh absolutely. My Facebook page header is a picture of these kids with signs like they'd done a seventh grade science project, just YOU ONLY LIVE ONCE in glitter.

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You know, people take YOLO in a negative sense, but to me it's very personal. I lost my brother at a very early age, at 33. He died very unexpectedly of a heart attack. My brother lived a simple life, he never really went to college. He worked with his hands for a living. But when he died, he had a three-month old baby, had just celebrated his first wedding anniversary, and it was the happiest I'd ever seen him. He didn't own much of anything. But when I stood in that funeral home and watched hundreds of people come by and tell all of these personal, amazing stories about things my brother had done for them—I realized the impact that this 33-year-old had on people. It made me change my values, change what I think is important. Like, Look at all this living he packed into 33 years. He failed at things, just like everyone, but all he ever wanted to do is get married and have a family. And he did. At least for a little.

So for me, that's everything. Especially with my artists. It's so scary to step out and follow your dreams. I have a strong understanding that you only get one shot at this life. It's short. You better step out and grab it, who knows if anything like this is going to happen again. So I'm trying to soak up what I can! Just trying to enjoy life and live large! I could die tomorrow. No one knows. You've got to pack all this living into this short time span we have. Who knows what happens after?

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I feel the same way.

And listen, I have the coolest job in the world. I get to help people find their voice. What could be cooler? What could be more personal? Your voice is you.

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Dionne Osborne is on Twitter.

Top image courtesy of Ruben Rivera; next two courtesy of Dionne Osborne; screengrab via Hulu; headshot by Mil Cannon.