The Goodnight Bar in Toronto is impossible to find if you don’t know where to look. Photos of dead dignitaries hang in the dimly lit, wood-paneled space. Drake shuts Goodnight down so it’s only his boys and me—oh, and a female friend who joins us later. Drinks flow courtesy of Mr. Graham. Blunts are rolled, sparked, and passed to almost everyone except Drake. It’s a good time.

When Drake talks about his Toronto movement, he’s primarily speaking about the people in this room. He’s glad to provide his friends with the means to better their lives. “All these people are happier than they’ve ever been,” he says. “They can afford to get their own place, get their own car, or maybe it’s just having a jacket, feeling a part of something. I’m embracing that role.”


I really, really love and care for Serena Williams. She’s definitely in my life and I’m in her life. It’s great to watch her play tennis. Very impressive.


Drake’s continued to put on for his city by shining light on a Toronto- based singer named Abel Tesfaye. You know him as The Weeknd. The 21-year-old with the wicked falsetto has put out two strong mixtapes, further establishing October’s Very Own as a force. “I wasn’t like ‘Yo, I’m looking for new artists,’ ” says Drake. “The Weeknd was presented to me, and anybody with any form of an ear can understand why I had to fully embrace that.”

“It’s our responsibility if there’s talent in the city to shine a light on it,” says Oliver. “That’s our duty. There were a lot of people that came before us that were extremely talented but I feel like they bred a generation of kids that didn’t fuck with them. That’s kind of the Toronto mentality: ‘Nobody respects you until the Americans respect you.’ But now I feel like we’re going to do the right thing and if there’s talent here we’re not going to pretend it doesn’t exist.”

Drake may only have one artist under his wing, but the number of women he’s associated with grows by the day. He’s talked at length about his heartbreak with Rihanna and his love for Nicki. Though he tries to keep mum, it’s impossible to tamp down speculation. He was recently snapped playing tennis with Serena Williams. Surely there’s more to their pairing than a couple of aces, right? Drake smiles and gives a ready-made response: “I really, really love and care for Serena Williams. She’s incredible. That’s someone I’m proud to say I know. She’s definitely in my life and I’m in her life. It’s great to watch her play tennis. Very impressive.”

When asked about Quincy Jones’s Harvard-educated daughter (and star of Parks & Recreation) Rashida Jones, Drake pauses, then offers: “Rashida has a beautiful, beautiful spirit. So talented, so funny. I met her at Rihanna’s birthday party. I was DJing and she liked my set.”

Around 2:30, Drake closes his tab, puts on his hoodie, and gives daps to everyone in attendance. The bar empties out into the alley and then into the street where a motorcade of Range Rovers waits to shuttle everyone home. Though they spend a great deal of time together, everybody in the crew takes time to say goodnight. This is what Drake means when he calls these people his family.

Like Wayne and Jay-Z, Drake intends to construct his own kingdom. A domain separate from the liars and haters. One where his friends lift each other up. But for that to happen, one needs a little Dame Dash and Birdman in them. You have to not give a fuck about anything.

Take Care, he says, will be the soundtrack for that metamorphosis. “Take Care has a lot of meanings,” he tells me. “It grew into a whole mind set... Never forgetting the past, but just embracing this moment and saying ‘take care’ to any doubt, any second-guessing. This is it. I have a great album. I have a great team. I have my visuals together. I have a great live show—those are all things that I know. I’m not doubting myself. I’ve never been in that position. This is my first time. And I hope I’m right, because I know I’m right to me.”

That’s why Drake walked off the set earlier. Had the shoot taken place anywhere else, or a year earlier, he would’ve been cool. But not repping the way he wants, here—in his own city? Nah, son.

Drake cruises the streets of his city in a black Range Rover.
IMAGES 2-4: Drizzy heads to Hong Shing restaurant for dinner with his October’s Very Own family. “This was the after-the-club spot,” Drake says. “I met one of my girlfriends here.” Seated to his left is Niko, Drizzy’s right-hand man and confidant. Neeks says Drake changed the sound of Toronto rap. “Drake came and flipped it and said everything that a hood guy can’t say,” he explains. To Neeks’s left is Future, Drake’s DJ. “Everybody in our circle is extremely grateful,” says Future. “We are the first ones to ever do this in our city.”
IMAGE 5: Drake and his OVO fam make it light up inside Toronto’s AME nightclub. “I’m about this young, energetic, hungry movement,” Drake says. “That’s what I stand for now. That’s why we put all this time and attention to detail into everything we do. It’s coming... and it’s better this way. Because if I was over-exposed, like in-your-face, that’s also when that light flickers out and you’re gone. I’m on my second album. I want to do this right for at least another 10 years. I’m not trying to rap when I’m much older than that. So I’m just taking my time.... I’m not Jay, I’m not 50 Cent—not yet. And even if someone would tell me I am there, I’m going to keep telling myself I’m not so I can work harder and keep building. It’s the same reason I don’t want to start a label and sign artists. I’m working on myself. I’m 25. I just want to be young and do this shit for us.”
IMAGE 6: Drake kicks back on the roof of his ride outside 15 Fort York, the apartment building where 40 and Oliver—one of his top producers and his manager—used to live.
IMAGES 7 & 8: Late night moves in the hallway of 15 Fort York, on the way to apartment 1503. “40’s room also doubled as the studio,” Drake recalls. “This is where we recorded most of So Far Gone.” Noah “40” Shebib says “Me and Drake created a niche where we create music in a certain way and people can recognize it pretty quickly. But there is another sound that came out of this city. That sound is from Saukrates and Choclair. Boi-1da has a pretty specific sound with his beats, which T-Minus also borrows. T-Minus learned from Boi-1da. He did a lot on Take Care as did Boi-1da, who also did work on Thank Me Later. So I think the new sound of Toronto—our R&B somber sound we’ve
created—is attributed to me, to Boi Wonder, to T-Minus, as well as Drake.”
IMAGE 9: Drake walks a lady friend by one of the stately residences on a road known as the Bridal Path. “I used to find motivation driving through this neighborhood,” Drake explains. “I would often tell girls I knew which one was Prince’s house.”
IMAGE 10: Heading home after a night on the town: “It’s a lonely life man. It belongs to the people, they go wherever they sell you. You travel according to however much money you want to make and who books you. And yeah, it definitely gets lonely even if you bring people along. It gets lonely two times for me: One, when I see people’s normal lives progressing, like falling in love, marriage, getting a job. When I catch glimpses of the life I could have had—not that I’d ever want to go back—but it does make you feel a bit like ‘Damn, I hope this is the right path.’ And then my apartment makes the weirdest noises at night. It’s super creepy and shit, so I hate sleeping alone.”

Special Thanks to the Thompson Hotel Toronto. Sweatsuit by North Star Sportswear. Varsity Jacket by October's Very Own. Pants by Engineered Garments. Boots by Timberland.

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