Artists
Smiley, Toronto Rapper, Age, Real Name, Height & Bio

Smiley The Rapper
Artist Age: 27 (November 23, 1997)
Stage name: Smiley
Birth name: Alexander Morand
Height: 5′9″ (175 cm)
Place of birth: Toronto, Ontario, Canada
Instagram: @thareal_smiley
Who Is Smiley Rapper?
Smiley Rapper is a Toronto-born artist known for his offbeat delivery, unique tone, and unapologetically local sound. Emerging from the city’s underground scene, Smiley quickly separated himself from the pack with a flow that breaks traditional rap rules. With early buzz in his city and growing attention from industry giants, Smiley Rapper has become one of the most distinct voices in Canadian hip-hop.
Smiley Rapper’s Rise from Toronto’s Streets
Smiley’s roots are deeply connected to the culture of Toronto. He began releasing music in the early 2010s, catching the attention of local fans who appreciated his slang-heavy bars and unconventional cadence. From the start, Smiley Rapper didn’t try to mimic popular American styles—he embraced the gritty, coded language of his city and wore it proudly.
His first mixtapes were raw and unfiltered, slowly building a cult following that would eventually catch the ear of Toronto’s biggest star—Drake.
Drake Co-Sign and “Over the Top”
The turning point in Smiley Rapper’s career came when Drake publicly co-signed him. This relationship evolved into their 2021 collaboration “Over the Top,” a booming anthem produced by Tay Keith. The track exposed Smiley to millions of new listeners, and his signature voice became a viral topic across social media.
While the co-sign brought fame, Smiley kept his sound grounded in Toronto, refusing to shift his delivery to appeal to the masses. Instead, he embraced the attention and used it to amplify his brand.

The Album Don’t Box Me In
In 2023, Smiley released his highly anticipated project Don’t Box Me In, which included a new feature from Drake. The album was a statement of self—proving that Smiley Rapper is more than just a viral name. It showed growth in song structure, production quality, and confidence.
The Drake-assisted track once again put the spotlight on their chemistry, but the album stood strong on its own. Don’t Box Me In pushed back against expectations and showcased the range Smiley had to offer.
Smiley Rapper’s Sound and Style
Smiley Rapper has built his career on doing the unexpected. His delivery is calm, almost whispered at times, but packed with slang, coded references, and punchlines that reward repeat listens. Some call it lazy; others call it genius. Regardless of opinion, it’s undeniably unique.
He’s also known for injecting humor into his bars, adding personality without gimmicks. That combination of humor, slang, and subtle confidence has kept fans intrigued, even when mainstream critics struggle to categorize his work.
Career Timeline by Age
Age | Milestone |
---|---|
17 | Begins releasing music in Toronto underground |
20 | Drops Buy or Bye, gains local recognition |
24 | Releases “Over the Top” with Drake |
25 | Signs to OVO, drops Buy or Bye 2 |
27 | Releases Don’t Box Me In with new Drake feature |
The Influence of Toronto on Smiley Rapper
Toronto’s influence runs deep in Smiley’s identity. From his accent and word choice to the cold beats and sharp slang, Smiley Rapper represents a style that is very specific to his city. He reflects the multicultural makeup of Toronto through his music and continues to keep the city’s underground culture in the spotlight.
Where many artists shift once the spotlight hits, Smiley doubles down on his roots. This loyalty to his original sound has earned him respect locally, even while critics remain unsure how to define him.
Smiley Rapper and What’s Next
Now at age 27, Smiley Rapper has proven that longevity doesn’t require compromise. With OVO behind him, a growing catalog, and a solid fanbase, he’s in position to take his sound even further.
What’s next may not follow traditional industry moves—and that’s exactly what makes his journey worth watching. Whether he leans into more features, experiments with new flows, or keeps refining what he’s already built, Smiley is determined to move on his own terms.
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