When life starts to feel like it's falling apart, sometimes a path toward a better outcome can reveal itself. In the case of Smiley, the off-kilter rapper from Toronto, his future in music didn't become clear until he got expelled from school in 11th grade. This happened within his first two months at an English school after he transferred from a French one. After seeing his friends freestyling, Smiley suggested they hit the studio. The session birthed their first song, "Too Much," as the Toronto rap crew Garden Gang in 2014. From there, Smiley continued to work on music despite legal issues, including an arrest for a gun charge and being on house arrest. Through the ups and downs, he's experienced an incredible 2021.

Smiley's song "Over The Top" featuring Drake, released this past summer, and took off on TikTok and streaming services. The success is thanks to Smiley's hook and feel for coming up with catchy lines, plus his long-built chemistry with The Boy. The track has been streamed over 68 million times on Spotify since its July release, and reached No. 57 on the Billboard Hot 100. With the new album Buy or Bye 2 out, and being signed to Drake's OVO Sound, the aptly named Smiley has plenty to be happy about.

Looking back at how he got here, in 2015, Smiley released "Garden Girl," the song that made him stick out from his Garden Gang crew. A somewhat love letter to local women, it's more aggressive than his current music, but the framework of how Smiley rhymes now is in the song. He originally wanted his flow to sound melodic, however, his voice came out with a lilt and a drag to it as he stretched out syllables. This was a stylistic choice that the rapper did more of as time went on. His track "9 On Me," also released in 2015, is what got him onto producer Boi-1da's radar, then soon after, Drake got put on. Smiley was in jail for a gun charge when the video for that song released in July of 2015. During that time, "9 On Me" was moving in Canada, and by the time Smiley got out of jail in 2017, Drake was publicly celebrating the rising rhymer's work, which supercharged his local buzz and output.

From there, he was dropping a project a year starting in 2018. The first installment of the Buy or Bye series arrived that same year, along with A Tape to Remember, then Road to Buy or Bye 2 (The Playlist) in 2019, and YYZ - LAX in 2020. Smiley's name only got bigger around Toronto after that. When it was time to make the real leap, he used "Over The Top," a song he recorded a year-and-a-half ago with Drake to be his major label debut. Soon after "Over The Top" released in July, Smiley was officially signed to OVO Sound/Warner Records. The relationship was years in the making, stemming from Drake's support of Smiley early on. This past November, he unveiled the Buy or Bye 2 project, which features the track that has earned him big looks in 2021.

Smiley's life has changed drastically over the last five years. He's focused on making music and staying out of trouble, along with a commitment to his fitness journey, which has both improved his physical well-being and mental health.

As "Over The Top" continues to climb and Buy or Bye 2 released, Smiley sat down with XXL via Zoom for this week's The Break.

Age: 24

Hometown: Toronto

I grew up listening to: "Lil Wayne, 50 Cent, Drake. Who else? I feel like it was always just songs, not even just artists, just like different songs that I always listened to. But those are the main artists from what I grew up listening to."

My style’s been compared to: "The only person I ever got compared to in ways of how I work and things I do is just actually Drake, to be honest. That's why a lot of people even hate on this song ['Over The Top'] because I'm bringing something new. So, it's like once they're used to it, then they'll accept it."

I’m going to blow up because: "I know once I want to go on the right path, I just know I have to be recording every day and I have to follow my certain everyday protocols and routine and then I know everything will always be going upwards. But I'm a routine guy, so, I just always have to be routine and then I always elevate, as long as the work ethic's there and everything's there."

What’s your most slept-on song, and why?: "I feel that my song that I just released on Buy or Bye 2 with Duvy, 'Topic,' I feel like that's a slept song. I feel like 'Breakdown' is a slept song as well. Most of my songs are realistically, I feel. Honestly, I feel like I'm still slept-on still, even after this. Nothing compares to actually what it is. All my numbers and stuff don't compare. Let's say my Instagram followers right now, let's say it's 89,000, it doesn't add up to when I go outside in the streets in L.A., anywhere. You'll think I have 5 million followers if you're to go out with me. And the love I get out there in the streets, like nothing ever adds up. I guess that's just the way it goes once you blow up."

My standout records to date have been: "['Over The Top'] .I don't know why but even that first Prada and Gucci [lyrics] connected so well that it was just like that first part and like the hook and obviously The Boy going crazy on the song, just that first part, just the Prada and Gucci, I don't know. It's that, for me, that made it big for me. I feel that's why that went crazy. And then it just went big on TikTok, even from the hate and the love. So, it just kept going crazy on TikTok and then it got pushed to radio, everything."

My standout moments to date have been: "Realistically, this whole experiment from after the 'Over The Top' drop. Right now, I'm doing... shows in Canada and all the big performances I ever done like at OVO Fest... just like the new life. I'm doing every day studio and just this whole experiment of feeling what it is and what you need to do to stay relevant. It's so crazy just knowing what it takes and everything. You don't ever want the moment to go away, too. So, it's such a crazy feeling. You just have to keep going and get that next hit."

Most people don’t know: "Actually, I'm starting to show it more on my socials and stuff, but like once you get to know me, I'm a funny guy and you'll really connect with me. Before, people used to actually be scared to come up to me in Toronto and stuff. They'll message me later on and be like, 'Oh, I just seen you there.' And I'll be like, Why didn't they come up to me? But now they come up to me because they see how I am. I'm not a serious person like that."

I’m going to be the next: "I want to be the next biggest thing to come out in my city and just in the world."

Follow Smiley on SoundCloud and Instagram.


"Over The Top" featuring Drake

"How Can I Miss" featuring OhGeesy


Buy or Bye 2

See Every Hip-Hop Song Certified Diamond in Music History

More From KOOC-FM