After graduating from university, Cuddy and Keelor formed a band called the Hi-Fis along with Jim Sublett on drums and Malcolm Schell playing bass.

In 1984 Cuddy and Keelor formed a new band, Blue Rodeo, with Wiseman, and recruited Bazil Donovan on bass and Cleave Anderson on drums as backup.

Guest performers on his solo albums have included Kathleen Edwards, former Weeping Tile member Sarah Harmer, and Wilco's Jeff Tweedy.

In 2016, Cuddy participated in a benefit concert in Edmonton, Alberta and another in Toronto, Ontario for the citizens of Fort McMurray, whose town was destroyed by fire.

In the 2007 edition of Canada Reads, an "all-star" competition pitting the five winning advocates from previous years against each other, Cuddy returned to champion Timothy Taylor's novel Stanley Park.