On June 12, 2012 Canning's new band, Cookie Duster, released their debut album entitled When Flying Was Easy. On July 13, it was announced that Canning would be scoring The Canyons.
On October 1, 2013 Canning released his second solo album You Gots Two Chill, the first to be released on his own record label Draper Street Records. The title of the album is a reference to the EPMD song You Gots To Chill. The first single Plugged In, was released as a free download off his website and Soundcloud page. Soon after the album was released he embarked on a North American tour with fellow Toronto band Dinosaur Bones, which included a headlining show at hometown venue Lee's Palace.
Canning signed Vancouver native Rosie June as the first artist to Draper Street Records. The label released her debut album Listening Post on June 17, 2014.