There are few careers in popular music any more versatile than that of Gordon Lightfoot. The native Canadian has enjoyed success in the worlds of pop, adult contemporary, and country -- with fans of all ages continuing to be enchanted by the singer’s unforgettable vocal approach.

At the heart of Lightfoot’s career is his songwriting. It’s fair to say that the singer bleeds lyrically through his material. Songs such as “Sundown” and “If You Could Read My Mind” revealed a man who knew his relationships could be imperfect at times. He also has quite the way with a story song, taking one of the great American tragedies of the 1970s, and crafting an unforgettable lyric about it. Here are 10 of Gordon Lightfoot’s finest moments!

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10. Gordon Lightfoot - "Dream Street Rose"

The title cut from his 1980 Warner Brothers release found Lightfoot in fine musical form. The guitar work added a layer of breeziness to the track, and his vocal -- as always -- was spot on. Lightfoot brought a definite warmth to the lyrics of the song, all about the positive effect the right one can have on someone’s life -- opening up a world of new possibilities.

9. Gordon Lightfoot - "Talking In Your Sleep"

A 1971 single for the singer, this one definitely ranks as one of his more underrated gems. There’s a heartfelt honesty that the listener feels when Lightfoot is pleading with his lover to explain the significance of the words that she uttered while sleeping. It wasn’t a major hit in the United States, but it’s definitely one worth seeking out in the Gordon Lightfoot song catalog.

8. Gordon Lightfoot - "Ribbon of Darkness"

This perfect fusion of country, folk, and pop appeared on Lightfoot’s 1966 United Artists debut album Lightfoot!. While the memorable track was released as a single by the singer -- who wrote the song. The original and hit recording of the song belonged to Marty Robbins, who earned a number one hit in 1965 with the song. Later in the decade, Connie Smith also covered the song, earning a spot in the Hot Country Songs Top 20.

7. Gordon Lightfoot - "Rainy Day People"

The singer earned a hit in 1975 with this moving number about those people in life that you might not hear from every day, but they always have an uncanny knack for being there just when you need them. The song originally appeared on the excellent Cold On The Shoulder disc.

6. Gordon Lightfoot - "Anything For Love"

The most recent Gordon Lightfoot song to appear on the American music charts came with this melodious romantic number, which hit the Top 20 on the Adult Contemporary charts in 1986, also earning him his last ranking on the Hot Country charts, as well.

5. Gordon Lightfoot - "Carefree Highway"

The lyrics of this Lightfoot hit from the fall months of 1974 came straight from real life. The character of “Ann,” with whom Lightfoot laments a failed relationship with, was someone that he once dated -- and yes, her name was Ann. The single was the second release from Sundown.

4. Gordon Lightfoot - "The Circle Is Small (I Can See It In Your Eyes)"

The song that earned Lightfoot his final ranking in the Top 10 on the AC charts in 1977 was one that actually had been around for a while. The singer had recorded it almost a decade prior in 1968 for his Back Here On Earth disc.

3. Gordon Lightfoot - "If You Could Read My Mind"

Lightfoot was a star in his native Canada, but when he released this song on Reprise Records around the Christmas season of 1970, it proved to be his ticket to success in the United States. This Gordon Lightfoot classic song -- written about the break-up of his first marriage -- has become one of his most covered tunes, with versions by Johnny Cash, Barbra Streisand, and Olivia Newton-John.

2. Gordon Lightfoot - "The Wreck Of The Edmund Fitzgerald"

Traditionally, story songs are a sure bet to make an impact with an audience, and Lightfoot put that theory to work with this hit from late 1976. The song was inspired by the real-life sinking of the ore carrier in Lake Superior that took the lives of 29 crew members in November 1975. After more than 40 years, this remains one of his best-written songs.

1. Gordon Lightfoot - "Sundown"

What goes on in a relationship when day becomes night? Apparently a lot, as Lightfoot confessed in this deeply personal hit from the spring of 1974. There has always been a sense of mystery about this Gordon Lightfoot song that remains his most essential hit single. Some have said the lyrics -- about the crazy depths that a relationship can take a person to -- were inspired by Lightfoot’s one-time relationship with Cathy Smith -- who later was involved with John Belushi, and served 15 years at the California Institute for Women due to her role in the comedian’s death. Lightfoot never had confirmed or denied the theory, but in 2008, he told Matt Fink from American Songwriter that “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,” without referring to Smith by name.