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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.