Bobby Dean Blackburn is a trailblazing blues, rock, and gospel singer whose life and career are deeply rooted in both music and history. A descendant of the Underground Railroad, his great-great-grandfather Elias Earls fled slavery and settled in Owen Sound, Ontario, where he and Sarah Woods became the town’s first mixed-race couple—often facing threats from the KKK and local prejudice.

Blackburn became known as the first Black entertainer on Toronto’s Yonge Street. His band, The Gems, began while he was still in school. Though threatened with expulsion for performing “rock ’n’ roll,” he left school at 16 and led the band to perform at the famed Zanzibar a Go-Go. Despite being the only Black member, his performances broke racial barriers and paved the way for future artists.

In 2010, he released his first album, Don’t Ask… Don’t Tell, featuring Liberty Silver and his sons’ Juno-nominated band, Blackburn. Sharing the stage with his sons remains the proudest moment of his career.

His influence extends beyond music—he was Mississauga’s first Black hockey coach and was inducted into the city’s Hall of Fame in 2016. Returning to school in his 50s, Blackburn earned his high school diploma and was named valedictorian.

With a lifetime of musical milestones and social breakthroughs, Blackburn’s legacy is one of resilience, artistry, and change. As he continues to perform, his story stands as a testament to perseverance and the enduring power of music across generations.