Cuddy, who met future songwriting partner Greg Keelor in high school in Ontario, was influenced as a teenager by singer/songwriters like Dylan, Jackson Brown, Gordon Lightfoot, and Kris Kristofferson, as well as by British Invasion groups. After university, Keelor and Cuddy started a punk-pop band called the Hi Fis. In 1981, the two moved to New York, and started a new band, Fly to France. After that group failed, Cuddy and Keelor decided to record a demo of their compositions, which included such later celebrated Blue Rodeo compositions as "Try," "Outskirts," and "Rose Coloured Glasses." In 1984, they moved back to Toronto, where a country-flavored "lonesome highway" sound was developing in the clubs, and sent the tape around. Through friends and newspaper ads the two formed the group that would become Blue Rodeo, whose highly lauded first effort, Outskirts, came out in 1986.

In 1998, in between extensive touring with the Rodeo, Cuddy released his solo debut, All in Time. Recorded at Toronto's Chemical Sound, the album featured Blue Rodeo bassist Bazil Donovan and keyboardist James Gray as well as a duet with Wilco's Jeff Tweedy ("I'll Make Believe It's You") and appearances by Sarah Harmer and Michelle McAdorey. ~ Erik Hage, Rovi