Is there anyone more on-brand than Smiley? For the last year, the rapper’s been unable to wipe the smile off his face. And for good reason. Since dropping his now-gold-certified track featuring Drake, “Over the Top,” last July, life has been very good for the 25-year-old: he lost a bunch of weight, inked a deal with OVO Sound, and currently hobnobs with the likes of Rick Ross and Druski. Not bad for a guy from Toronto’s underserved Pelham Park neighbourhood who spent much of his youth in conflict with the law.

But you know what they say about things that go up, and Smiley isn’t looking to come down anytime soon. In true hair-of-the-dog fashion, he’s been searching for another chart-busting hit to sustain his buzz. 

“I’m working on a new album and I’m trying to just get that summer smash,” he tells Complex Canada. “Last year we dropped that “Over the Top” and we had that summer. I love that feeling. That’s why I want this summer again.” 

Today, he unleashes a new song that could be a summer smash contender. “Rush Hour Freestyle,” produced by Toronto beatsmith Bavaro, is a gritty, hypnotic bop that hears Smiley flex on the haters praying for his downfall. We’re premiering the video, helmed by Jonas Picasso, below.

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The OVO rapper knows full well the attention he gets isn’t all positive. His soft-spoken-yet-menacing flow—delivered in a classic Toronto mans accent—hasn’t rubbed everyone the right way, so much so that Jake Paul, of all people, had to come to his defence last year, tweeting that “rap critics who don’t actually appreciate different styles of rap are the worst.” 

But Smiley isn’t letting the naysaying break his stride. On our Zoom call, he beams non-stop, even after coming straight from a full interview on OLG’s sports analysis show Game Plan. Fresh off receiving a shout-out from BIA on “London,” her recent hit with J. Cole (“Singin’ with Smiley, speak of me highly,” the L.A.-based artist raps on the track) and a feature on “Miss You,” the lead-off track on DJ Charlie B’s much-anticipated debut Across The Board, things are looking up for him. This may well be the summer of Smiggs after all.

Smiley opened up to us about receiving both high praise and hate, a potential BIA collab, Drake’s latest advice, and his “flawless” next album. The convo, lightly edited for clarity, is below.

My guy, Smiley! The last time we spoke was right before “Over the Top” dropped and everything changed. How’s life been for you since then?
It’s worse. I have to work harder. [Laughs.] I’m just messing with you. I’m loving every level of this, you know? But I do actually have to keep working harder. There’s just a lot of more moving around, flights, all this. Right now, I’m just trying to stay in the studio. I just wanna sharpen my skills. I wanna practise my different voices. I’m trying to use AutoTune, trying to get better bars out there. I’m trying to make a full song that’s 100 percent strong, with less fat parts. I want everything just structured better, you know? 

Do you have a new album in the works?
Yeah. I’m working on a new album and I’m trying to just get that summer smash. Last year we dropped that “Over the Top” and we had that summer. I love that feeling. That’s why I want this summer again. I want the big loves. [Laughs.] So we’re just working right now. We’re gonna keep trying to drop singles for the whole summer. 

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So, the people need to know: Why don’t Prada and Gucci go together?
I don’t know, it was the first thing that came to me. And, like, realistically, I actually just don’t see it going together. I guess it could go together, but I don’t see it. Like Louis and Dior, those ones, they look like they just go together for some reason. There’s some brands, when they go together, you can’t do it. [It’s a] mismatch. By itself it’s good, but together? Nah.

“[Drake] just said that’s what it is when you bring something new to the table. That’s what they’re gonna do, and then there’s going to be a shift happening where they’re gonna start understanding it and messing with you.” – On receiving hate

Did you have a feeling that line would go viral the way it did? 
Yo! No. I don’t know why it went so viral like that. But honestly, when I did think of [the line] as I was driving, it was like something that I knew had to go there. I had to stop the car and write it down before I forgot. And it was even better when it took off, you know? The song’s already hard with Drake on it, but I felt like if that line wasn’t in there it would have been a way less successful song. Just because it’s like a feature song, you know? So I had to play my part on it too for it to be a hit. 

Yeah, man. It’s iconic now!
I know, man. Next show, I’mma be like “When I say Prada and Gucci, y’all say, ‘Don’t go together!’ I’ll go crazy with it. [Laughs.]

Smiley posing in front of palm trees
Image via David Delrosario

The song has also had its fair share of haters. I know when Drake first came out, he had a lot of haters too because he sounded a bit different. His style was very unique at the time. Has he given you any advice on dealing with negative energy like that?
Yeah, he just said that’s what it is when you bring something new to the table. That’s what they’re gonna do, and then there’s going to be a shift happening where they’re gonna start understanding it and messing with you, and that’s gonna be done from there. And that’s actually what happened, you know? At some point in time, a lot of people were saying, “This is actually hard.” Even Jake Paul did a tweet saying that. It was such a crazy thing, too, because I don’t know why the hate took up so much people’s attention. For Jake Paul to even do that tweet, that meant it even came across to him—even he saw all the hate. A lot of people were even messaging me like, “Are you OK? Yo, don’t listen to them.” I’m like, I’m good. What the heck? They thought I was crying in the basement. [Laughs.]

BIA recently gave you a shout on “London.” How’d that feel?
“Singing with Smiley, speak of me highly!” Yeah, that’s my gang and ‘em. I love BIA. She was one of the first people to show me love from America. She actually did a video call to intro Justin Combs and their management team [to me]. I love her! She’s my guy! [Laughs.] I love her music.

“They’re gonna hear singing Smiley and they’re gonna be confused.”

So she reached out to you first?
Yeah, we both went back and forth from that first time she did that video call. That was my first time seeing her. And then I was like, that’s Diddy’s son’s there too? I was like, this is my way! I thought I was hitting the market already, but I’m kicking that door down to the States now, boy! And from there, it’s just been love from the both of them. We’ve been in touch. She bigs me up in the song, you know? 

That must have felt good, to get that recognition.
Yeah, it does. It was even a big thing in Toronto when it happened. I love those things, you know? I can’t wait to just do something with her one day. We’re gonna rock the hell outta that.

So a collab with BIA is in the works?
It should be. We’re working. She’s just on tour right now with Russ but when she gets back to L.A. we’re supposed to link and work on something. 

What’s the latest advice Drake gave you?
A lot of people tell me, “Oh, it’s good to network and stuff, to go outside.” And I asked him, what, really, would you tell me is more important for me to do? Do I really need to do the networking and going outside? I’m in the studio all day but do you think at nighttime, those things are important to do? And he said, “Oh, it’s all about balance.” But then his second part was like, “Nothing can save you but a good album.” That’s the real answer right there. That’s why now I just wanna get better every time on my music and just release a flawless album.

I saw you were recently at a game for Drizzy’s basketball league, the SBL.
Yeah, I was over there. I saw them do their tournament. That was actually my first time at his house. We did a little house tour. I’m like OK, this is how it’s going to look when I have my mansion. [Laughs.]

Did you play him one-on-one?
No, no, no, no. [Laughs.] It was a tournament set up with actual teams. One day I will play him actually, when I get better. I don’t wanna get embarrassed. But once I get the proper skills? It’s over. I’mma be Iverson on the court. Then I’ll challenge Drake. 

During our last chat you said you guys were supposed to have a ping-pong showdown. Did that ever happen?
Yeah, we never did. Whenever we’re in the same place with a ping-pong table, though, it’s on. I’m gonna spike that thing [does serve motion]. But yeah, we’ve never been together somewhere with a ping-pong table.

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That’s convenient for Drake.
You see when I beat YK Osiris in ping-pong?

No! What?
Yeah, I played YK Osiris and I beat him. He called me out at first too. I was like, what the heck? He’s good, I won’t lie. He’s good. It’s just that I’m better. [Laughs.] No, no. The thing is, I’m actually not that good. But I’m good at my serves. And I’m good at reflecting everything back. I can keep going. And once I really get confident on that, then I start doing the quick ones, you know? That’s how I keep getting better and better.

Who do you want to challenge next? 
I need my rematch with Pressa because he got me one night when I was tired and he actually beat me. That’s been on my mind. Once we get back to a ping-pong table, I want my rematch with him. We were too late into the night. Like, he’s good but I was doing so much stupid stuff. I was missing stupid stuff. It wasn’t making sense. I was like, what the heck? But it was 21 to 20, so it was close.

So what’s this new album sounding like? What can you tell me about it? 
I want this album to actually be the one, you know? 100 percent. All in. I’m just recording a whole lot of music. It’s bare different styles, and I’m trying to go more fast tempo. I’m just trying to practise a lot of different things. I want to learn more pitches, because sometimes people might say, “Oh use this voice and this or this,” so I wanna practise it to know how to use each voice every single time. And I wanna master AutoTune. I like doing those types of songs now even more because it’s just like singing your emotions. I feel like it’s therapeutic too.

That’s interesting. I don’t think I’ve ever heard you sing.
Yeah, I know. I have a few songs like that but I haven’t put them out yet because we want the right one, you know? I just wanna make everyone get at me, like with “Over the Top” again. [Laughs.] They’re gonna hear singing Smiley and they’re gonna be confused. They’re gonna be like “What the heck’s gwanin with him?” But I like my voice when I’m singing. It becomes deeper. I say stuff in that voice sometimes around girls… and they love it. [Laughs.] Oh my gosh. They like it! So, you know, we’re gonna shake them up a bit.