2 December 1955, Toronto, Ontario, Canada. Cuddy began playing guitar at around the age of 10. Drawn to country music though his admiration for Hollywoods singing cowboys, in particular Roy Rogers, he maintained his interest in music throughout his school years and after university he and childhood friend Greg Keelor formed a band. Mostly, the pair wrote their own songs and in 1981 they moved to New York City, forming a new band they named Fly To France. Playing music from a variety of genres, they struggled for a few years but by the mid-80s were back in Canada, settling in Toronto where they formed yet another band, Blue Rodeo, a name also used for their recording company. With Blue Rodeo, Cuddy had a string of successful albums for WEA Brothers Records. Cuddys solo debut, All In Time, picked up glowing reviews and won a 1998 Juno award.