Canning began performing in the 1990s,[1] singing and playing guitar, bass and keyboards in several local bands, including hHead and By Divine Right.

[citation needed] In 2009 Canning took part in an interactive documentary series called City Sonic, which featured 20 artists from the Toronto area.

On June 12, 2012 Canning's new band, Cookie Duster, released their debut album entitled When Flying Was Easy.

Soon after the album was released he embarked on a North American tour with fellow Toronto band Dinosaur Bones, which included a show at hometown venue Lee's Palace.

[6] Canning's last album, Home Wrecking Years, was released in August 2016; it includes cameos by Justin Peroff and Sam Goldberg from Broken Social Scene.