Maestro Fresh Wes Gets ‘Stamped’ Into Canadian History
By: Jenna Hobin
Banner Photo Credit: Andrew Williamson Photography
Maestro Fresh Wes has never been one to chase moments—he’s built a career on lasting ones. Now, after close to four decades as a household name in Canadian culture and beyond, that longevity is being literally ‘stamped’ into history.
In honour of Black History Month, Canada Post has unveiled a stamp celebrating Maestro Fresh Wes, also known as Wes Williams, as part of a special set paying tribute to pioneers of Canadian hip-hop. He appears alongside Michie Mee and Muzion—a recognition not just of impact, but of perseverance.
“I feel this is one of the biggest accomplishments I’ve ever had in my life,” Maestro says of the honour. “It’s a blessing to continue to grow and professionally evolve and this stamp is a once in a lifetime opportunity.”
For an artist whose career has constantly evolved—rapper, producer, actor, author, philanthropist and more—the stamp represents something deeply personal. “I celebrate the longevity of my career and that’s something I’m most proud of,” he explains. “There’s a lot of artists that don’t last that long.”
That idea of longevity runs through every chapter of Maestro’s life.
(CNW Group/Canada Post)
Before receiving awards or gaining international recognition, Maestro Fresh Wes was an emcee on radio stations across the GTA from 1980 to 1986, building his name across the city. That journey eventually took him to Ottawa, a city he credits with honing his focus.
While in Canada’s capital, Maestro attended Carleton University, studying law and political science while continuing his artistic path.
“Ottawa means a lot to me because that’s when I really decided to take my career really seriously,” he says. “One of my memories at Carleton is that it is when I found myself. It was me being alone… it’s when I found ways to excel in a safe environment where I felt supported.”
Two years after arriving in the capital, Maestro was opening for Public Enemy in Ottawa, a milestone in his early career. “It was no longer about making demo tapes or rapping on the radio or opening up for U.S. acts,” he recalls. “It was now about making records and getting a record deal.” As he puts it, simply, “Timing is everything.”
That timing led to his 1989 hit “Let Your Backbone Slide”—a defining moment in Canadian music history. The track became the first Canadian rap song to reach the Top 40, the first to go gold and remains one of the most recognizable singles in Canadian hip-hop to this day. And history, Maestro explains, should always be the goal.
“Don’t make records, make history,” he says. “Because anyone can make a record, but making history is when you do something or say something to people that keeps them checking for you years later.”
In 2024 alone, Maestro received the Governor General’s Performing Arts Award for Lifetime Artistic Achievement and was inducted into the Canadian Music Hall of Fame, a year underscoring his continued legacy. The Canada Post stamp, unveiled at a ceremony in Toronto on January 27, raised the bar even higher.
Today, Maestro is based in Saint John, New Brunswick, where his creative outlets continue to expand. The same day he was celebrating the unveiling of the stamp, he also found out he’d been nominated for a Juno Award for Back to the Time Machine, a children’s album created about a father-and-son duo. He’s also featured in The Slack, a maritime thriller filmed near his home, where he plays a police officer. The series premiered in February on Bell Fibe TV.
Even as his career keeps growing, Maestro remains committed to giving back. Through the Maestro Fresh Wes Scholarship, he supports Black students in skilled trades at New Brunswick Community College and Nova Scotia Community College—an initiative he’s immensely proud of. From a “giving back” perspective, he says, it’s about encouraging young people “to strive for greatness in whatever they want to do in life.”
When asked what advice he offers those chasing their own aspirations, he says, “Ask yourself what makes you different from everybody else? What can you do that makes you stand out?”
“It is one thing to assimilate and another to innovate,” he adds. “And I like to surround myself with innovators.”
By following his own guidance to stand out and innovate, Maestro Fresh Wes has built a career and a legacy that resonate across generations, and we can’t wait to see where the years ahead take him.