Drake is the type of artist whose technical abilities make a noticeable jump with every release. When in late October he dropped three new tracks, a few members of Jezebel staff noted that Drake was sounding like a properly impressive R&B vocalist: comparing "Days In The East" to 2009's "Best I Ever Had," for example, you can hear a real increase in control, depth, ease and decisivenesswhile his distinct, diffuse vocal texture remains.

We surmised that perhaps a mastermind vocal coach was behind this improvement, and we found Dionne Osborne, who's been working with Drake for more than four years. Dionne and I spoke on the phone last week.

Hi Dionne!

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Hi! I just have to ask you, how do you pronounce your name?

"Jia." Oh, you get it. Do you get lots of "Diane"?

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Diane, Donny, oh my Lord.

"Donny Osborne."

Oh, when I was a kid in the rural South, it sucked. I grew up in this rural area of North Carolina, and though it was great growing up there, I just couldn't get out fast enough. My dreams and my heart were bigger than the town I grew up in. I ran right out of high school, to Boston. I was this little country mouse when I got to Berklee [College of Music] but I loved it. I got some time to grow up there—but after eight years of snow shoveling, I couldn't take it anymore. So now I live in Atlanta. It's cultural, but it's got that Southern flair. It's the #3 city in terms of the music industry. We just surpassed Nashville, I think.

And it's having quite a hip-hop moment.

Georgia is a hotbed of musical talent in lots of different genres. You have a lot of hip-hop artists who were in LA but moved or got places here in the ATL. There's a pop-rock scene coming back, and country will always have good roots here, and then there's gospel and contemporary-Christian, of course.

It's when you moved to Atlanta that you started teaching.

Yes. I'd been singing in a band, was doing commercial jingles, stuff like that. People used to tell me that I should be a teacher, but for a while I still believed that only the people who can't, teach. And that's total crap. Teaching is an awesome creative process. Every person is like a new puzzle. You have to figure out, how are you getting that sound out, and how do I stop it? Singing always came so naturally to me, and working with people for whom it doesn't is a big reward.

You worked with the first woman ever signed to Rocafella/Def Jam, right?

Teairra Mari, very briefly. She was wickedly talented and one of the prettiest girls I've ever seen: like Tyra and Beyonce put together. I wish I'd had more time with her. They called us in to get her ready for her label showcase—she had a really smart A&R person who knew she needed some help, and when I showed up she was trying to do her choreography in shoes that were two sizes too big for her and she didn't even know how to hold the mic. I really felt for her. As a singer I knew what it was like to be that vulnerable.

And now you've been working with Drake for over four years. How did you get hooked up with him?

The call came into my colleague, Jan Smith, at Jan Smith Studios. At the time, Jan was on the road with Justin Bieber. She had also worked with Keri Hilson, whose team also managed Drake at the time. They called her because Drake was about to do his first tour and he needed someone to prep him. It's amazing that some labels/teams will send out artists without any training, even if they've never even played hole-in-the-wall bars. But they were smart enough to bring someone in.

So, Jan sent me to Toronto where they were doing rehearsals. I think I was supposed to be there for three to five days. I felt a bit of trepidation, because, Jia, here's the real truth: rappers only come to us when they already have vocal damage, and it's kind of too late to help. And going in, you don't know who wanted you there, the artist or the management team. You don't know if they're going to fight it.

So I show up early and the band is drilling me with questions. What are you going to do? What are you going to do to him? I start talking to them about health stuff, and they're like, He loves his sweet tea. You're never going to get him to give up his sweet tea.

Then Drake walks in with his posse. You know how rappers never go anywhere without a big group of people. And he stuck his arms straight out and gave me a big hug and that was it.

That was it!

You know, Drake is so funny. Later on he was like, "I looked at you and I just knew I was going to love you." He is exactly what you see. People say he's corny, or he can't be that nice, he can't be so sweet. But I can tell you, he was raised by his mother and his grandmother. He's had strong love from strong females. And we just totally connected. Maybe because he was an actor, I don't know—

He was open to taking direction.

Exactly. She's here to help me. After that first session, he just kept stretching it out. It went to seven days, and then past that into the tour.

Is this Thank Me Later Drake? Earlier?

It was the mixtape, So Far Gone, and he was already pretty huge. On our first session, I told him that my goal was to make him a singer who raps, not a rapper who sings. I know Drake loves rapping, that's his first love. But the road is just littered with rappers who sing. They all try it. If you love music, you love singing, but not everyone succeeds.

So on that first tour, we're on the road, and Cortez Bryant, Lil Wayne's manager, comes up to me and says, "Drake told me you changed his life." I just started laughing. He said that? But what I do think I did, honestly, was that I was the first person who treated Drake like a professional singer. I said, "Here's the deal. You have to change your diet. You're heading out on tour in the spring and not thinking about your asthma or your allergies. You've got to take care of yourself too. Let's focus on helping you do your job."

What was your first impression of Drake's voice? What was it like, technically?

Well, obviously I'd done my research. 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.

One thing we worked on right away was his live sound—he had this tone that he didn't use in his recordings, this thin tone to make the sound cut. It was whiny-sounding to me. Actually, once I said, "You sound like an uptight white Jewish dude!" He started laughing really hard and later on, I was so embarrassed, because I found out he was Jewish. But he was just trying to get the sound out and make an impact. He was worried it wouldn't sound cool enough or hit hard enough live.

Part of the problem was his approach physically. He'd be bending over to the floor and doing all of this crazy stuff and I'd be like, "What are you doing? Your diaphragm is totally curled over." We talked a lot about body structure, too. It's important for every singer. It's not rocket science, but you have to understand the body. From there we worked to bring out that natural, dark, strong color in his tone that he uses so well, now. We grounded his sound. Made him support more from the diaphragm and the lower abs.

How did you deal with translating that to tour life?

The first tour, honey—I was horrified. This major rapper was onstage just screaming at Drake and I remember Drake turning around on stage to look at me, and I tried to hide it, but my face must have been horrified. Let me tell you, rappers are the most underserved artists in our industry, and they are grossing the biggest bucks! They desperately need coaching. They come out and it's like four of them, all yelling! All yelling the same thing. They're not even yelling different bars. They're not even layering themselves. They're not even yelling the right pitches. They're yelling the lead vocal up the octave and they sound like some random dude in a basement screaming along to their own songs. Like bad karaoke. Not like the artists they are.

It just sounds horrible. But then again, if you don't know what you're doing, you do need three other dudes to do it along with you.

The year we did the Club Paradise tour, we had J. Cole, Waka Flocka, Meek Mill, French Montana, and it was just amazing and crazy. I think the other acts changed some, watching Drake. I loved watching the evolution of all of the artists that summer. It was dope.

What about after the show, when it's the after party?

The tour itself is already so intense, you know: that first tour, Drake was doing a 60-minute set, we didn't even have an opener, he's sleeping on a tour bus, eating crappy food, and he was recording his album. But he's still got to go to the after parties. So, I went out with him the first two nights on tour to help him learn how to manage that on the road. These club owners were sending out thousand-dollar bottles of champagne. Drake's the biggest sweetheart, and he's cool with me just standing in the VIP area with him. Unfortunately, everyone thinks I'm his mom, not someone there as a professional.

Hahaha. Oh my god.

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!

What a dude.

I've never had anyone trust me implicitly like he did. He really opened up his heart and his brain. Even after all this time, he rarely doubts me. He wants to get better and he did from the very beginning. I'm very proud to say that even when I'm not there, he's drinking water. He says "Goodnight, God bless, I'm Drake, take care," and he gets offstage and starts cooling down his voice. He takes a chef with him, he works out. He's doing it on his own now.

What other kinds of stuff do you have him do?

I've told Drake a million times, we need to do a workshop. No one's really telling hip-hop artists how to take care of themselves—they have short careers, they live it large and hard, with the smoking, the drinking and the partying. My point has always been that the competition is so tremendous, and you must do everything to make the most out of this moment. If you want to be those artists, if you want to be an Eminem or a Kanye, you have to go smarter, not harder. I try to get rappers to remember, you use the same vocal cords that Usher does. Imagine what Usher would sound like if he was smoking a pack a day and never touched a vegetable.

A lot of it was educating his tour group about how to help him manage being on the road. I took him to a Wal-Mart in the middle of Kansas, or somewhere, and made them put a humidifier on the bus. He needed the humidifier on the bus because it was so dry in there. Later on in the tour, Drake thought he was having trouble singing, so I showed up to help. He was getting his haircut and I took one look at his face and said, "Oh, baby, you're sick." I could see it in his eyes. Well, after sending one of the guys back on the bus to retrieve the humidifier, I opened up that humidifier and I just wanted to kill somebody. I laid into them, "You see this pink stuff? THIS IS MOLD. THIS IS WHY HE'S SICK."

Singers have fragile ecosystems. He's got spring allergies on a spring tour and yet they were letting him sleep all the way up to show time. You can't just immediately roll out of bed onto the stage and be a rock star. But they all learned how to help him and Drake changed his habits. Before the next tour, he called me up and was so proud of himself. He said, "Didi, I got a trainer, I've been working out, and I haven't had any sweet tea." I was so happy that he was taking it seriously, and he saw the difference. He would come offstage and and say, "I could go another set."

That frees him up to focus on the connection he makes with his fans in his shows. I tell him, "Drake, people are drawn to your music for a reason. You're saying things people want to say, but can't." The first time he felt that connection for real it was a religious experience. It really is a high, for everyone involved. The audience is looking to be acknowledged. Everyone wants to be acknowledged. Drake gets blasted by the media for one part of his set where he calls out his fans. It stretches out long, sometimes 15 minutes. But it's great and he loves it. He goes section to section, people have signs, guys are holding up their prosthetic legs. It's crazy. They need to know he sees them, and he does.

Drake is particularly good at inflecting his rap with a discernible pitch. What is that like to coach—the modulation of melody into a rap line?

You just made the hair on my arms stand up! I'm so glad you recognized that! You know, I am sort of like a gardener with Drake. I plant seeds in his head. I keep watering them and then eventually they grow into something good. I told him, "Baby, listen, you're rapping over music. The music has a key. There are eight pitches you can choose from. Choose one, any one and go from there!" Once he heard how much better the whole song sounded, he took off with it. As a musician, it makes it so much more listenable to me.

Right. I don't think people often think about rap, or speech either, as having a correlative pitch.

Absolutely. We all speak with pitch. Drake was doing the remarkable thing of rapping in the right key! And he always pitched his raps around where he wrote the melodies.

So, during one tour, I told him, "Drake, you know what would be really cool? If you could flow directly out of your raps into the melody and and go right back into the rap. Just flowing back and forth, back and forth." He told me later on, "You said that to me and it kind of pissed me off. I thought I was already doing that." But then he went home, listened to his stuff and started working on it. He got what I was saying. He's got that ability and he improved.

I mean, singing is just exaggerated speech. You're sustaining the tones; you're holding the notes longer. So I tried to get him to do that more with rap, connecting his flow. It's like writing in cursive. The technical term is legato. It's a better use for the air when you're singing and makes for a better sound overall.

Interesting to think about legato into rap, which has to be percussive.

You're right! It's just like being a dancer. You've got sharp movements, but they move smoothly from one to the next. When Drake first started he was having trouble jamming up his phrases. So we broke them apart, slowed them down, cleaned up the rhythms, found what he wanted to stress in every phrase. And when you put it back together, you realize you have plenty of time to do it. You're hitting the right beats and everything's connected. You're like a hot Latin dancer who's got that fluidity even though you're popping the moves.

That's one of the first things I notice about rappers, the way they handle emphasis in their phrases. I love that. Can you rap, Dionne?

HECK NO. But yeah, I do know all the words to Drake's stuff, I'm side-stage with my microphone, talking to him on his in-ears during the show, sometimes rapping along with it. People get so tickled! Drake laughs at me too. A middle-aged white woman going all-in on "Show Me A Good Time." But I am a great lover of lyrics, and some of those songs are just wonderful. I love his insight.

What are your favorite Drake songs?

You know, vocally, I love, love, love "Karaoke." So beautiful. I love the groove and the melody. And he sounds so smooth!

I was going to ask you about "Karaoke!" It's the same range as "Hold On We're Going Home" but the tone sounds so different.

And he's bringing more new stuff to his singing. This past November I heard him do it at the Houston Appreciation Week. He was doing all this falsetto stuff, and I was just jumping out of my skin. Love it!

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—"

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.

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!

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.

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—"

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.

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.

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.

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.

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.

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."

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.

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.

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.

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?

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.

Dionne Osborne is on Twitter.

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