When he was a relative newcomer to American audiences, Lightfoot was already 30 years old and a seasoned songwriter and singer, well respected in his home country, and fairly well known within the folk community. Distinctly Canadian, Lightfoot had an impressive body of work that covered a wide range of territory, from slow romantic ballads to traditional folk, all delivered in his robust baritone voice.

Like many songwriters of the era, Lightfoot followed Dylan's path toward Nashville in 1968. He began working with producer John Simon (the Band) and utilized some of the same Nashville musicians that Dylan had employed during the Blonde On Blonde sessions. Although the results were somewhat erratic, Lightfoot's songwriting remained consistently strong.

Lightfoot was still a few years away from real stardom outside of Canada, but his songwriting craft and distinctive voice was easily as appealing as his more recognized later work. His songs reflect many themes that he would return to throughout his career. Lightfoot would continue to gain recognition for his writing, with the likes of Bob Dylan, Johnny Cash, Harry Belafonte, Judy Collins, Marty Robbins and even Elvis Presley covering his songs, but few could improve on Lightfoot's own delivery. Although he deals with universal themes, Lightfoot and his songs remain the living, breathing embodiment of Canada.