The first Gordon Lightfoot composition to become well known, this song was composed by the Canadian singer-songwriter in 1964. The tune describes a down-on-luck man far from home, observing the takeoff of a Boeing 707 plane. According to some sources, it was inspired by Lightfoot seeing off a friend at the Los Angeles airport.
One of Gordon Lightfoot's most covered songs, this was first featured on Judy Collins' Fifth Album, before its release by the Canadian singer-songwriter. Not much later it was recorded both by Ian & Sylvia as the title track of their 1965 album and by Peter, Paul & Mary for their See What Tomorrow Brings set. Other notable covers include ones by Bob Dylan on his 1970 Self Portrait LP, Elvis Presley, whose version can be heard on his 1972 Elvis Now disc and Paul Weller, whose interpretation reached #40 in the UK in 2005.
Peter, Paul & Mary's version reached #91 on the US pop charts, the only time the song has reached the Hot 100.
Elvis Presley also performed the song during the USA airing of his 1973 Aloha From Hawaii via Satellite TV show. Lightfoot recalled during a 2014 Reddit AMA that it was the favorite cover of any of tunes. "I got a lot of attention on that song," he recalled. "I tried to meet him once, but Elvis had left the building. I never got to meet him, I never did, I almost got to meet him but I never got to meet the guy."
Gordon Lightfoot told Mojo magazine regarding Bob Dylan's cover: "I was totally blown away that he would record one of my songs in the first place. It helped my career - I'd not had a hit single myself at that point. His cover was a linchpin in that whole process because it made people in the industry aware that I was producing good songs."