Sundown (Gordon Lightfoot), 1974

There are rumours that “Sundown” was inspired by his then girlfriend, Cathy Smith, later more infamously known for her involvement in the death of John Belushi. Lightfoot has commented in interviews that she was “the one woman in my life who most hurt me.”

More, from Cathy Smith’s wikipedia page:

Catherine Evelyn Smith (born Catherine Evelyn Smith, 1948 in Hamilton, Ontario) is an occasional backup singer, rock star girlfriend, “groupie” and drug dealer, who served 15 months in the California state prison system for injecting John Belushi with a fatal dose of heroin and cocaine in 1982…

…Smith became an employee and then mistress of Canadian singer-songwriter Gordon Lightfoot in the early to mid-1970s. At one point, she even drove their tour bus. Smith sang backup on Lightfoot’s song “High and Dry” which was on the Sundown album. She apparently sang more backup on the album but Lightfoot mixed most of it out.

By several accounts, the Smith-Lightfoot affair was volatile and illustrated in the lyrics of “Sundown”, Lightfoot’s Number One hit and most financially lucrative song. It reflects the dark feelings Lightfoot was experiencing at the time. Drinking too much and married to another woman, he on one occasion broke Smith’s cheekbone in a fight. Lightfoot has stated of his three-year relationship with Smith, “I was sometimes crazy with jealousy”.

Picture of Cathy Smith, from this amazing website:

Once, on a bus between Vancouver and Whitehorse, I heard a woman tell the story of how Gordon Lightfoot kissed her one time.