Jim Cuddy and Greg Keelor have been friends since high school; both attended North Toronto Collegiate Institute. It was not until after University, though, that they decided to form a band. Their first band was called the Hi-Fi's, with Cuddy and Keelor along with Jim Sublett on drums and Malcolm Schell playing bass. The band released a single in 1980 featuring "I Don't Know Why (You Love Me)" and on the B side "Look What You've Done". The record was not a big commercial success, though, and when they couldn't get a record deal in Toronto, they headed off to New York. 
No breakthrough happened in New York, either. However, they did meet up with Bob Wiseman, who would later be their keyboardist in Blue Rodeo. They eventually moved back to Toronto, forming Blue Rodeo in 1984 including Basil Donovan on bass and Cleave Anderson on drums to back up Cuddy, Kealor and Wiseman.
In the 2004 edition of Canada Reads, Cuddy advocated for Guy Vanderhaeghe's novel The Last Crossing, which won the competition. 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. In 2013, he was made an Officer of the Order of Canada along with Greg Keelor, "for their contributions to Canadian music and for their support of various charitable causes".