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McCulloch also directed the music video for the Tragically Hip’s song “My Music at Work,” for which he won the award of "Best Director" at the 2000 MuchMusic Video Awards.
In the beginning, they started as an opening act for such bands as The Pogues, Tragically Hip, George Thorogood, and Junior Wells, but it was not long before they grabbed the main stage themselves.
In 1995, The Tragically Hip performed the song on Saturday Night Live.
Many influential albums have been recorded by artists such as The Tragically Hip, Sam Roberts, Bruce Cockburn, Hugh Dillon Redemption Choir, Blue Rodeo, Cthulhu martini, Fred Eaglesmith, Sarah Harmer, By Divine Right and Stripper's Union.