Rise & Grind is a new editorial series, meant to introduce and dissect new, buzzing, or underground artists.


Toronto’s takeover is currently underway. The Screwface Capital’s Big 3 -- Drake, Tory Lanez, and The Weeknd -- opened doors for the Canadian city to finally break out south of the border. Pressa, who previously appeared on Rise & Grind, has been a fixture on blogs and playlists for the past 12 months while Smiley, OVO’s latest signee, recently celebrated his first Billboard Hot 100 entry with “Over The Top” featuring Drake.

Smiley’s proximity to Drake dates back a few years ago, when the Certified Lover Boy rapper publicly co-signed Smiley on his Instagram page. Then, there was the infamous DM exchange with Toronto rapper KG, who called Drizzy a “p*ssy” before calling Smiley’s music “trash.”

“Smiley eating your food in the city along with like 10 other n***as,” Drake responded. 


The fateful co-sign eventually evolved into a deal for Smiley who recently released the sequel to his 2018 project, Buy Or Bye. Laced with A1 production from Runitup Beeze, Tay Keith, and CashmoneyAP, Smiley’s finally making a formal introduction to the American market, similar to Pressa, who appears on the project, did with the release of Gardner Express

For this week’s edition of Rise & Grind, we chopped it up with Smiley about his stomping grounds in Toronto, Buy Or Bye 2, and clarified his contribution to Drake's CLB

Stay tuned for a new installment of Rise & Grind every Monday.


smiley new interview ovo drake
Image provided by Warner Records. Photo credit: Chris Reign.

Stomping Grounds:

I’m from the west side of Toronto, around the neighborhood Pelham Park. It’s around St. Clair and Keele. I was born in Montreal, but then I moved to Toronto when I was 3 years old. Growing up around my neighborhood, there was a lot of trafficking going around — drug trafficking. That was everything I was seeing around my neighborhood. It was crazy. Other than that, my older brother always raised me the right way. He was kind of like a father figure to me because my dad got out of the picture when I was like 4 or 5. Him and my mom, they guided me the right way, raised me the right way, but as far as my neighborhood, that’s what I was seeing everyday -- the older guys doing this drug trafficking stuff.

Growing up, at first, I was more reserved. I didn’t like to chill around people. I never went to people or my friends’ houses. I would rather just stay at home and play Call of Duty. Later on, my brothers would tell me, “Come outside with us.” So many times, I kept saying, “No, I don’t want to go.” And then one day, it was summertime, and one of my older brothers, he wasn’t taking no for an answer. I went out with them, and from there, I was just like, “Yeah. This is fun.” I don’t know what I was missing! 

They were popular at the time. All the girls wanted to chill with them. They were the fresh kids. We would always link at a park, and then all our friends would come to meet up and chill there, and we would either go to all-ages clubs or someone would get to rent us a hotel, and we would invite all our friends and all the girls. We’d get kicked out in like an hour, and then we would just go back to the park and chill there. That was the fun part.

Zodiac Sign:

I’m a Leo. The best birthday months ever. I’m August 6, 1997. Everything they said about Leo’s, I think that’s actually me. Let’s say if I see good results, that motivates me to go even crazier. I can’t think of them all right now, but every time I see things about Leos and what they say, I’ll be like, “Yeah, that is me!” I feel like I’m 100% all of those things.

Top 5 DOA:

My top 5 rappers: 50 Cent, Lil Wayne, Drake, Lil Durk, and Lil Baby. It’s not in order, but those are probably my 5. The first 3 are the ones for sure, but the other 2 are just what I could think of that I’m listening to right now.

50 Cent’s Get Rich Or Die Tryin’ -- that was the first album I ever bought. I had a lot of memories growing up with that album, and it was just what I was listening to going to school. This makes me wanna rap. That, and then Lil Wayne --  the same thing. When he dropped Tha Carter III, that was that same feeling. And then, for Drake, it’s the same thing too — all the singing songs and rapping. Growing up, I was always listening to it. I feel like, at that point, I manifested this whole relationship that we have.

Biggest Accomplishment:

I feel like my biggest accomplishment is the Hot 100. Debuting on that was pretty big for me, and performing at Lyrical Lemonade. And I feel like, right now, I’ve got into a space where every day I’m recording. It’s good to be in that space right now because it’s making my music even better. I’m very focused. I know I’ll be able to achieve everything I want to if I keep going this way.

I always cared about those types of things. I would always want those [Billboard] accomplishments. It’s so funny because before it got out there and I had seen that [I made] number 57, I made a song 4 days ago. I manifested that too! I’m just like, ‘Billboard charts, n***a, you understand me?’ Then 4 days later, Hot 100. I was embracing it all. Now, I want number one. It’s a good thing.

Studio Habits & Essentials:

My first thing before was inviting too many people to the studio. I don’t have this habit anymore. We would catch a vibe, it’s good, and we would get drunk and high, but not a lot of work gets done. It just gets annoying if the engineers are telling people to be quiet, and you’re trying to make the song and you have to do another take. It gets annoying and frustrating, so that was something I didn’t like. Now, I just go alone to the studio, just me and the engineer. 

I need my water— a lot of water. I need green tea. Like right now, if I walk into the studio, they already have green tea ready for me. And I need my earpods. Those are the 3 things I need. I like to listen to the beats in the headphones before I write to it. 

"Over The Top" ft. Drake:

He sent me the beat, and he already had his part of the hook on it. This one, as soon as I heard it, I was in the car and I was listening to it -- it was a vibe right away. It sounded like a club banger. I wrote my first part of the song, like ‘the Prada and Gucci’ -- I was just freestyling in the car. I liked that part, so I remembered it, wrote it down, and when I went to the studio, I put that there. From there, I kept writing my verse, and I finally got a verse. I put it down. And I was just like, “Yeah, this is sounding like a banger.” He rocked with it. I asked him if he was trying to drop it right now, and he was like, “You wanna drop it after my album or before?” I was like, “Before,” and then he made it happen. That was big.

He liked it right away, and I told him, “Yo, I don’t know if I should redo my verse. I think I could do better, but I don’t know.” He was just like [laughs] “I hate when you say that” ‘cause on another song, I said the same thing. He was like, “I hate when you say you want to switch your verse. Just be confident in your verse and just keep it. I f*ck with it.” From there, he gave me that confidence.

After that, I feel like anything -- I just have to be confident. With rap and stuff, a strong part is confidence, too. I have to be more confident in the way I think and everything, and still be humble, but just be more confident. From there, I kept working the same way. Even though I would record something, I know that I should do it better, but I’ll still move a little more confident, at the same time. I’ll even be more confident with my delivery and the way I’m saying it.

First Bars:

It was f*cking sh*t. It was so long ago. I actually have been rapping for a long time but when I was young, we’d take breaks, you know? So, I actually don’t remember my first bar ever, to be honest.

​​I was in the courtyard in my neighborhood, and we were just all freestyling. I wasn’t freestyling, my friends were freestyling, and they were all excited. They wanted to go to the studio. I don’t know why they were excited that day like that. One of our older heads that was rapping at the time, we asked him, “Where’s the studio you go to?” He was like, “Oh, it’s right down the street.” He booked a session for us, we went, and then two of their friends, they put their part. They were kind of rappers already, but never made songs. They would freestyle. They did their part, and they wanted me to go on it, but I’m like, “What the heck? I’ve never done this before. I don’t rap. I don’t freestyle when you guys freestyle.” I was like, ‘Alright, I can’t punk out.’ I wrote something. It took probably 2 hours. I went in there and did it, but it was crap. [Laughs]

First Show:

It was so crazy. My brother, he would always tell me to go do the shows. An older guy in my neighborhood named Blacka, he was doing shows and stuff. My brother was like, “Just go do it.” I was shy at the time. I was like, “F*ck, nah! I’m not going to do a show, fam! What are you talking about? No one even knows my sh*t. I don’t want to embarrass myself, and we have to pay to perform?” I forget who it was, but we had to pay to open up for them? Are you crazy? I would’ve done it, but I was just using that as an excuse at the time. After I had a little buzz, my first show paid us like $250, something crap like that, but I still did it because I needed this practice. I knew that this was the right time. I was ready to do it. I would’ve done it for free at the time. I didn’t care, but I was ready at that time to do shows.

It was good because, at that point, when I started getting booked for these things, too, I had this one song that was bubbling. I had two songs. I had the “Intro” song that -- remember, Drake was in a pool, singing to the song, which boosted the song everywhere. Everyone messed with that song. And I had another song called “Body.” I already knew, “Okay, this is the confidence I need. They already know my two songs, so now I’m ready.” I’m not going to go out there where I’m just singing to the air! From there, the reception was great. They were screaming it. The DJ muted the one part, and they would’ve known the bar. Five months later, I opened up OVO Fest.

Clocking Out:

The music they would not expect me to listen to is some R&B music, a lot of old-school music. Like the singing music, too, like, the girls singing -- a lot of those things I listen to [are what] people wouldn’t expect me to listen to.

And the other day, we were coming back from bowling. I was drunk. I wanted to play the Black Eyed Peas’ “I Gotta Feeling.” I told them to play that. Random stuff like that, I was just feeling like that. People wouldn’t expect me to want to listen to that sh*t, but I like all that music. It’s good music.

Up Next:

Right now, I’m about to do an album rollout. My album’s coming out, Buy. or. Bye 2. It’s 15 songs on there. You’re just going to see the whole journey. Like, me working out, getting to my ideal body weight goal, and just working hard, trying to motivate these kids and everyone. That’s the vibe I’m on right now.



What should fans expect on the new project that’s different from the first Buy or Bye, and what should they expect that will be familiar to them?

I feel like what’s different would probably be [that there are] more features on there because Buy or Bye didn’t have features. And more confidence, faster flow. And things to expect, for my hardcore fans, they’ll know that some songs are kind of the same Buy or Bye 2-type of stuff. I feel like it’s just going to shock people. This project, I was just listening to it the other day, and I was like, “Yeah.” This time, I can actually say, “Yeah. I’m happy. I’m excited.”

I know Drake’s been rocking with you heavy, but a leaked DM came out, and he was like, “Smiley is eating your food in the city.” It was before your buzz was on a national level within Canada. What was your reaction to seeing such a bold cosign in a private conversation?

I was like, “Yeah, this guy’s riding!” He didn’t have to do that, and no one would have ever seen that if that kid didn’t go and post the sh*t, so that meant a lot for me. I was just like, “That’s the sh*t I like to see.”

How much of that was a confidence boost leading up to what you were doing following that moment?

It was a confidence boost because I knew this guy -- ‘cause if you know why he was mad and saying, ‘Why are you supporting Smiley?’ and all this sh*t. I was like, ‘I like to see those things because it means something good is happening.’ People get mad at that. They hate, or it’s always a conversation about something. It motivates me more.

Touch on OVO Fest. 

Looking back at it, I’m like fuck. That was my first time doing an event. That was an 18-minute performance, and I was just like, “F*ck.” From there, even leading up to the performance, I was doing bare cardio because I was like, “Oh, f*ck. I have to do 17 minutes.” I did what I could at that time, but that’s when I realized that I’m not in the state to do this sh*t for 17 minutes. That’s why I’ve been working out a lot. I don’t want to go through that sh*t again. I’m sweating like crazy, I’m out of breath. But you learn through all these things. That’s why now, I want to be a better performer.

I believe it was your birthday weekend, as well. I think you played “Stare.” That’s one of my favorite songs. 

That’s the thing, too. Next time, I come back to OVO Fest, I know it’ll be way better. But there too, I feel like, at some point, I was just like, “What am I even doing right now?” It doesn’t feel like I’m catching the people’s attention right now! Well, I am catching their attention ‘cause they’re just like, “What’s this guy doing?” or whatever, but they don’t know my songs. I hate that feeling, especially performing. I like to perform and everyone knows my sh*t. Every song, I want it to have that feeling, with people going crazy to it. That’s what I do it for. That’s what I wanna do it for. 

It’s also the biggest stage in the city. 

It’s crazy, too, because that was my hometown. That’s why when I come back, it’s gonna be different.

The night before CLB dropped, you popped up on his Instagram story, and he was like, “Smiley just dropped a verse on the album,” but you’re not on the final tracklist. What a lot of people were saying was that he was borrowing your flow on “No Friends In The Industry.” At the end of the day, what was your contribution to the project?

I don’t see none of these things that everyone’s talking about, but even if it was, it is what it is. Those things are good things. That’s what a lot of people do. I didn’t see that. I don’t know what people were talking about. I was just there to support him at his release party, to show love and all that. That was my contribution to the album.


Favorite track on the album?

“N 2 Deep” and “Fair Trade”. Those are the main two. All the other ones, I like too, but those are the main ones I like. Oh, and the one with Lil Durk too.

It seems like the American market hasn’t fully embraced you the way they have with some of your peers from the city. But your cadence, your flow, and even your confidence on the mic, it’s just so different. What do you think is misunderstood among hip-hop fans in the States?

I just had an interview with Adam22 the other day, and he told me, “I feel like you’re what the industry’s missing.” I actually do pay attention to those things. I did see that, at some point, when “Over The Top” dropped, there was a lot of hate. At some point in time, it shifted to a lot of people saying, “This is actually hard!” I saw that shift happening. And then, I see there’s actually a lot of Americans who are tuning in now. Even now, when I go outside, in Los Angeles when I just walk, I’m getting noticed left, right, and center. I see it happening, and right now, with my album dropping, it’s gonna happen. I just feel like, ‘Why hasn’t it happened yet?’ I just need to put in more work. They know my face. They know me. As soon as I just go, something’s gonna happen, and they’re gonna accept me. 

You probably already had that popularity aspect just within Toronto, especially when your music took off. How does it feel seeing that in LA where there are so many artists? 

It feels great, too. Yesterday, I was telling my manager. I’m like, “Fam, I’m actually a guy out here! I can’t just do what I want anymore.” I could still do that, but I’m getting every picture. At my gym, people are like, “Oh, you’re Smiley! Picture?” All that is motivation. It makes me feel good. I feel like what’s gonna make me go, too, is my Instagram and TikTok. That’s the sh*t. Shout out Cardi B -- my girl Cardi B -- as motivation for my social media. I like the way she handles her social media, and that’s one thing I like about where I’m going too. I like my social media a lot more now, and that’s just another thing of mine that will take off. 

For people who are not as familiar with your work, can you explain what “Buy or Bye” is?

Please, just don’t waste my time. You’re either gonna do it or not. You’re either gonna be with us or not. It’s either do something or don’t. Stop telling me all this other shit. Stop loafing around, or doing nothing. It’s literally that. The easiest way [to describe it] is you’re at a store, and you’re either gonna buy it or bye, leave the store. Don’t go asking all these questions. If you don’t have the money for it, you’re not going to buy it and you’re just wasting these people’s time.