The 10 Most Influential Canadians From Scarborough, Ontario

Image via Complex Original

Before Drake, someone had to pave the way for Canadians in mainstream hip-hop. That person was Maestro—also known as Maestro Fresh Wes. Often referred to as “the Godfather of Canadian hip-hop,” Maestro was the first to ever do it, releasing his debut album Symphony in Effect back in 1989—the first album by a Black Canadian artist to be certified platinum in Canada. From that album came the highly-regarded hit single “Let Your Backbone Slide,” now cemented in Canadian history as the first rap song to be inducted into the Canadian Songwriters Hall of Fame. Pretty nice for a song he wrote while working as a security guard at Scarborough’s Parkway Mall. For a Canadian rapper in the '80s, the hill was steep. There were no hip-hop labels, radio stations, or even a hip-hop category at the Junos to be recognized in (Maestro was nominated for Best Dance Recording at the 1990 Junos because the hip-hop category didn’t even exist yet). It was Maestro’s pure grind that made something out of nothing, broke down barriers, and helped make Canadian hip-hop what it is today.

We can’t talk about influential Canadians from Scarborough without talking about Jamaal Magloire. He’s long been a source of national pride as one of the first Canadians drafted to the NBA—back then, only in the company of Steve Nash and Todd Macculloch. To put things in perspective, Canada didn’t even have a team in the league until his later high school years at Eastern Commerce Collegiate. Through his 12 NBA seasons, he’s become a pioneer and an inspiration, showing young kids from Scarborough and beyond what’s possible. Perhaps the sweetest part of his career is how it’s come full circle—finishing his last year in the NBA as a Toronto Raptor, and now serving as their Basketball Development Consultant and Community Ambassador.

At only the age of 23, WondaGurl has achieved an enviable career—and she’s done it all while being a trailblazer as a female producer in her male-dominated field. This Scarborough-born prodigy started learning how to make beats from YouTube tutorials at the age of nine, continuing to master her craft into her teens when she competed in Toronto’s Battle of the Beat Makers competition. Not only did she win, but her skills had impressed judge Boi-1da (also on this list), who took her under his wing. With his guidance, WondaGurl went on to amass credits on hits like Rihanna’s “Bitch Better Have My Money,” Travis Scott’s “Antidote,” and Jay-Z’s “Crown.” All this success and she’s barely at her peak —her WondaChild label imprint hints at plans for a full-out dynasty. This hometown hero proves that despite perceived barriers associated to age and gender, sometimes pure talent and hard work speaks for itself. 

Far from his days on Degrassi, Scarborough’s Stephan James has gone on to make an indelible mark on Hollywood—but to say he hasn’t looked back wouldn’t be entirely true. He’s landed breakthrough roles in films like Selma, If Beale Street Could Talk, and Amazon Prime thriller Homecoming, but this Golden Globe-nominated actor hasn’t forgotten where he comes from. He and his brother Shamier Anderson—an established actor in his own right—created the annual B.L.A.C.K. Ball to support opportunities for up-and-coming talent, especially those from marginalized communities. Growing up in Scarborough and raised by a single mother, James has become committed to seeing more youth from diverse backgrounds thrive in performing arts. That commitment is why the B.L.A.C.K. mentorship group (which stands for Building A Legacy In Acting Cinema and Knowledge) has teamed up with the Canada Media Fund’s ‘Made’ campaign to raise awareness about Canadian talent in the entertainment industry. James may be a rising Hollywood star, but he doesn’t want to close the door behind him—working to make sure that youth from Scarborough (and places like it) know that they can make it too.

The story of Drake’s meteoric rise to fame can’t be told without recognizing Boi-1da’s influence on his early music and beyond. His beats on Room for Improvement, Comeback Season, and So Far Gone will take you back, but one sticks out as most notable: Drake’s breakout hit “Best I’ve Ever Had,” the song that catapulted him into stardom. Boi-1da—also known as Matthew Samuels—grew up in Scarborough, but it wasn’t until his move to Ajax that his interest in music became a full-fledged passion for beats, and ultimately a career. The Pickering High alumnus put his name on the map by competing in Toronto’s Battle of the Beat Makers and winning the competition three years in a row with his distinct sound. Fast forward to today, and that sound has been sought after by the likes of Rihanna, Eminem, DJ Khaled, and Nicki Minaj—helping to shape hip-hop as we know it, and inspiring a new generation of Canadian hitmakers.

You don’t have to agree with Jagmeet’s politics to admit he’s a pretty cool guy. He represents a generation of young politicians changing the face of public office in Canada, unafraid to use social media to call out his opponents or make viral TikToks. Even Rihanna’s a fan. She started following him on Instagram—a subtle endorsement that shook things up as Jagmeet was running for Prime Minister in Canada’s 2019 federal election. Jagmeet’s story starts in Scarborough, where he was born, and takes him through India, St. John’s Newfoundland, and Windsor as he moved around during his childhood. It’s a story of triumph despite challenges —in a recent tweet Singh opened up about the ‘violence of hate’ he experienced growing up, and reveals even more about his unsettled upbringing in his autobiography Love and Courage. Even though he’s faced adversity, Singh holds the honour of being the first turban-wearing Sikh to sit in Ontario’s legislature, and the first racialized leader of a major national political Canadian party.

Lilly Singh is one of those people you might have been able to guess is from Scarborough. Maybe it’s the way she embraces her ethnicity, or that her experiences growing up with immigrant parents are just so relatable to Scarborough kids.

Whether you’re a fan or not, the first time you saw an ad for Lilly’s late-night show, A Little Late with Lilly Singh, you couldn’t help but feel a sense of awe. The show meant that she had broken the seal between YouTube and network television, becoming the first woman of colour to host a late-night show on a major U.S. network since Wanda Sykes and Monique. She’s made out nicely from her humble beginnings in Scarborough, getting her start as one of the OG viral YouTubers. Billions of views later, Lilly’s gone on to appear in feature films like Bad Moms and Fahrenheit 451, published a book, and is set to star in an NBC TV series fittingly titled Bright Futures.

Kardinal helped to move Maestro’s work forward by creating more space for Canadians in mainstream hip-hop, most significantly by earning acceptance beyond the border. His childhood was spent in Scarborough’s Flemingdon Park, where he was raised by Jamaican immigrant parents—an influence that’s almost inextricable from his music. Hits like “BaKardi Slang,” “Everyday (Rudebwoy),” and “Feel Alright” exemplify how his unmistakable style blends both hip-hop and dancehall. What’s most significant about Kardinal’s career was his ability to cross over to the U.S. and work with producers and artists like Lady Gaga, Timbaland, and Pharrell Williams. He became the first Canadian rapper to peak at No. 3 on the Billboard Hot 100 with Akon collab “Dangerous,” leading the way for Drake to follow and hopefully many more to come.

From Scarborough to Saturday Night Live—who would have thought? Myers’ hometown still remains a little-known fact to many Canadians who might not be able to picture Austin Powers coming from Toronto’s most eastern borough. After graduating from Stephen Leacock Collegiate Institute, Myers joined Toronto’s Second City comedy troupe where he honed his comedic skills before eventually getting the opportunity of a lifetime. In 1985, fellow Canuck Lorne Michaels invited him to fill a guest spot on SNL. He went from guest to regular cast member as his popularity grew, creating iconic character Wayne Campbell along the way. The '90s cult classic Wayne’s World soon followed and made bank at the box office. Mike’s career took off. When it comes to Hollywood actors, Mike Myers is truly a comedic genius, making him undoubtedly one of the most prominent talents coming out of Canada. It’s the reason he received the rare honour of having his star added to Hollywood and Canada’s Walk of Fame.

As one of the biggest stars coming out of Canada in recent years, The Weeknd has done his hometown proud. Born Abel Tesfaye to Ethiopian immigrant parents, he was raised by his mother and grandmother in Scarborough until dropping out of Birchmount Park Collegiate to take music seriously. His debut mixtape House of Balloons ended up being the catalyst to his career—well, that and Drake’s co-sign. It had a sound so distinct and atmospheric, you probably remember where you were when you first heard it. The music’s air of mystery was propelled further by his anonymity—for years, fans didn’t know what he looked like.

Today, The Weeknd has a look, sound, and brand all his own. He’s credited for redefining R&B—and seriously, you can hear his imprint all over the current pop landscape. His chart domination, meanwhile, speaks for itself—earlier this year, he became the first artist to lead the Billboard 200, Billboard Hot 100, Billboard Artist 100, Hot 100 Songwriters, and Hot 100 Producers charts simultaneously. His single "Blinding Lights" also just became the longest running Top 10 hit in history. Shockingly, the album that broke all those records, After Hours, was just shutout of the 63rd Annual Grammy Awards, receiving zero nominations. But Tesfaye doesn't need a hunk of metal to prove what we all already know: he's not only a hella influential Scarborough man, he's one of the greatest Canadians of all time.