Meet Smiley, OVO’s New Secret Weapon

Toronto rapper Smiley gives his first interview since announcing he’s signed to OVO Sound and collaborating with Drake on his new single “Over the Top.”


Photo by David Delrosario


Smiley, true to his name, can’t stop grinning. The 24-year-old rapper is sitting on the other end of a Zoom call and beaming from ear to ear while talking about his come-up. 

He has a lot to be happy about lately. Coming from Toronto’s Pelham Park neighborhood, Smiley first started buzzing in his hometown thanks to a unique vocal delivery that makes him immediately stand out on any song he touches. Then, he caught the attention of Drake. 

“I saw he started supporting me, and he followed me on Instagram,” Smiley says of his first interaction with Drake back in 2017. “Then we just started communicating from there.” The following year, he released his debut project Buy. of. Bye., and it’s only been up from there. 

This July, Smiley and Drake dropped their first collaboration, “Over the Top.” The aggressive rap record earned him his first Billboard Hot 100 entry, peaking at No. 57, and helped introduce him to a wider audience shortly after signing with OVO Sound. Smiley tells Complex that the deal happened just as organically as his rise to fame. “That’s family,” he says of his new label. “I feel like I wouldn’t choose it any other way. It’s the home city, the biggest artist, and it’s how we are together. It feels good. It was the right thing to do.”

Now, he’s preparing to release his next album, which he reveals will include 15 tracks and some potentially explosive collaborations. In his first interview since publicly signing to OVO and collaborating with Drake, Smiley spoke to Complex about linking with the Toronto superstar, his upcoming album, and where he wants to take his career in the future. The conversation, lightly edited for clarity, is below. 

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How did you first get into rapping?

I was always into music. I never wanted to do it until a lot of my friends started doing it. Then one day I just asked one of my boys if we could go to the studio. He set it up for me and I made my first song there with my boys. We were like a group, and we released it two weeks later. We did a music video, then we started getting a buzz from there. We made a lot of noise in the city, and it just made me want to keep going. 

You used to go by the name Smiley_61st. Why did you decide to drop the “_61st”?

My first name was actually Double B, which stands for Big Boy, but I didn’t like the name. I needed something that was catchier, so I came up with Smiley_61st, and that was during my first year of rapping. Then I switched my name to just Smiley, but my social media was all Smiley_61st. I wasn’t happy with that, so I just changed everything to Smiley.

How did growing in Toronto shape your sound?

The everyday situations I had to go through and the ups and downs made my music angrier. Even leveling up and getting better in my career makes my music different. A lot of things I went through made my music the way it is now. Sometimes it’s angry stuff, and sometimes I’ll talk about the good stuff.

How would you describe your sound?

I think it’s a laid back, slow kind of sound. Now, I try to speed it up more, but it’s kind of slow, laid back, and aggressive.

You said your songs can be aggressive, but you haven’t stopped smiling during this conversation. Where does the aggression come from? 

My name is Smiley because, for some reason, I’m always smiling. But behind it, there’s a lot of anger that makes me seem angry in the booth. That’s where my true feelings come out. When I’m in the booth, I can talk about what I really want to talk about.

When did you realize that you were on Drake’s radar?

I knew I was on Drake’s radar in 2017. I saw he started supporting me, and he followed me on Instagram. Then we just started communicating from there. I sent him music, and he would always give me feedback. We built a relationship through that, and it was genuine the whole time. It was always love. 

What was some of the early feedback you received from Drake? 

The first feedback was when he commented on a social media post that was a blog posting my song. That was the first comment that he left, and from there was the first time I knew he paid attention.

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How did it progress from talking on Instagram to connecting in person and signing with OVO?

It was really him messing with my music. He fucked with me heavy, and I fucked with him heavy, too, so it was always meant to happen.

Why did you choose to go with OVO? What about the team made you feel like it was the right move?

That’s family. I wouldn’t choose it any other way. It’s the home city, the biggest artist, and it’s how we are together. It feels good. It was the right thing to do.

How has OVO helped you with your career so far?

All of them told me to continue doing what I’m doing—just going harder. I have to go harder now and keep working on my craft. There was always support from [Mr.] Morgan, Oli [Oliver El-Khatib], 40 [Noah Shebib]. It was good.

How did “Over the Top” come together with Drake?

Drake sent me the Tay Keith beat, and I was like, “Oh, this is hard.” I vibed with it. Right away, when I was in my car listening to the beat, there was already a hook on it. From the beginning, I put the whole, “Prada and Gucci, it don’t go together.” That was the only thing I came up with at first, so I went to the studio and laid that down. It took me a long time to actually get the right verse I wanted. I probably did three different verses for it, but I had to sit down and find the perfect one, because it was so much pressure when you’re going against the greatest artist like that on the same song. You want to make sure everything is right.

What is your creative process normally like when making music?

When I started making music, I would just go off of vibes in the studio. I would get drunk and vibe out. My friends are there, there’s girls in the studio, and it’s just a vibe. It gets easier. But now I’m on my health journey, so I try to put the drinking and weed to the side, and I do it sober. I’ll find a beat in my email, I’ll listen to it, and if I like the beat I’ll start writing to it in my notes. Then I’ll go to the studio and spit it. But sometimes I’ll go into the studio and try to freestyle it, because I feel like I’ll have a better delivery. I do it differently sometimes, but I try to do it sober. It’s harder now doing it sober, though. It feels like a job. 

Can you talk more about your health journey? What made you want to go this route? 

Right now, I’m going on a 30-day fitness journey. I’m not smoking or drinking. I’m eating healthier, and I’m trying to do the music as much as I’m doing the workouts. I knew I was going to be around a lot of cameras, and I knew I wanted to do big tours and stuff. I didn’t want that laid-back, fat guy energy. I want to run that stage and be healthy. I always knew that’s what I wanted to do, but now I have more motivation to do it. Now I have more time. In LA, I get to do more things and be more creative. I feel better when I’m healthy. I’m in good spirits. A lot of people are even saying that I’m inspiring them, and I love to hear those things. That’s what I want to do: inspire these people.

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Do you have any other collaborations with Drake or any other artists on OVO?

Right now, we’re just finishing the album. I want to surprise everyone when I release the tracklist. It could be announced soon.

Is there anything you can tell us about what we can expect from the album?

I think you should expect a lot of different sounds and feelings. Right now, there are 15 songs on there, and I’m positive about it. I feel like everyone will like it, so I can’t wait for everyone to see it.

Is there a date yet?

It’s still in the works right now, so I don’t have an exact date, but it should be soon.

Who are your dream collaborations?

There’s a lot, but I’d say Kodak Black, Lil Baby, Cardi B, and Nicki Minaj. 

What do you hope to accomplish this year?

To be honest, I feel like right now I’m blessed to be where I’m at. It’s the biggest accomplishment that I’ve ever seen before. To add on to what’s going on right now would probably be my album going No. 1 or getting a No. 1 Hot 100 song. That would be what I’m looking forward to.

What are your long-term goals?

I want to have a lot of accolades. I really want to give back to my family and the community. My No. 1 thing is to be the greatest at it and become a billionaire. I just want to get the most I can out of this. I want No. 1 Billboard Hot 100s, I want a lot of those. I want Grammys and everything.

What’s something about you that might surprise people?

My personality. I feel like if I were to be on Instagram Live more and post more things about me, people would see I’m really funny. I feel like my personality and charisma are up there.

Are you planning on showing more of your personality on social media soon?

That’s the other reason why I say Cardi B, too, because I like the way she uses her Instagram freely like that. I guess I’m getting better, because before, I didn’t post at all. I was more kept inside. I didn’t want to really show that side of me. But now, it’s coming out. I don’t care anymore, and I see that’s what fans like anyway.

What are your thoughts on Toronto’s current rap scene?

I like it. I feel like all the artists are going hard in the city. It’s sad that a lot of them passed away or are going to jail, but they’re very talented. I listen to a lot of Toronto music, too, so I love our rap scene. They just need to stay focused and do their thing musically.

What would you say is the best advice you’ve received so far?

It was probably to stay the same and keep going hard with the music. Don’t ever feel like I have time to take a break because of where I’m at now. I have to go harder right now. Also, before I was so anxious to get to this level or even further, but I was told you’ll miss these moments. Right now, I really have to go 1,000 times harder. 

What’s the most important thing fans should know about you right now? 

I’m just trying to make the best music for you guys right now, and there’s so much more coming.

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