For Canadian singer-songwriter Gordon Lightfoot, finding success in America was long and arduous affair. Lightfoot finally broke through with his first top 10 hit in 1970 with the single "If You Could Read My Mind," which peaked at #5 in early 1971. The song came from his sixth studio effort, Sit Down Young Stranger.
It would take Lightfoot four more years and four more albums to reach the pinnacle of #1 with his tenth LP, Sundown. Released in January 1974, the full-length hit #1 on the Billboard 200 over the week of June 22, 1974. For the title track and lead single, it took an additional week to reach the top spot. The song assumed the peak position of the Hot 100 for the week of June 29, 1974.
The song, about a man stressing over the thought of his significant other being swept away about another man, was an exceedingly real slice from Lightfoot's own life: "I had this girlfriend one time, and I was at home working, at my desk, working at my songwriting which I had been doing all week since I was on a roll, and my girlfriend was somewhere drinking, drinking somewhere," he revealed during a Reddit AMA in 2014. "So I was hoping that no one else would get their hands on her, because she was pretty good lookin'!"
It has been assumed that the woman Lightfoot was writing about was Cathy Smith, with whom he had a contentious relationship. Smith is infamous for her connection to late comedian John Belushi, and involvement in his drug overdose death in 1982.
"Well, it’s got a good beat to it. It’s got interesting harmonic passages," Lightfoot elaborated to American Songwriter in 2008. "It has a great arrangement and not too bad of a vocal. If I was going to do it again, I’d probably try to do the vocal again. I’d do it the way Jesse Winchester does it. It comes out a little bit funkier. He’s great. I was on a roll writing a whole bunch of songs at that time, and it was one of your typical insecurity-type songs, a 'where is my baby tonight' kind of concept [laughs]. People can relate to that. It’s that concern about not being totally in control of a given situation. I was writing a whole bunch of stuff at that time. I think my girlfriend was out with her friends one night at a bar while I was at home writing songs. I thought, 'I wonder what she’s doing with her friends at that bar!' It’s that kind of a feeling. 'Where is my true love tonight? What is my true love doing?' I guess a lot of people really do relate to that. That’s part of romance…that wondering."