Let me state from the beginning that any list of The Top 20 Greatest Singer-Songwriters is subjective. This is only my opinion, reflects my own musical preferences, and includes those whose music I know and listen to. And, on any given day I might argue that the order and/or content should be changed. This is how it seems to me today at this moment.
For a songwriter, you don’t really go to songwriting school; you learn by listening to tunes. And you try to understand them and take them apart and see what they’re made of, and wonder if you can make one, too.
— Tom Waits (b. 1949) American singer, songwriter, musician, composer, and actor
The criteria I used to determine The Top 20 Greatest Singer-Songwriters:
- Mostly wrote both the lyrics and music for the songs.
- Performed them either as a solo, duo, or led a group.
- Examined the quality and variety of songs.
- How prolific is the songwriter.
- Their overall influence on other musicians (and the surrounding culture).
- Have achieved success singing their own material. (For example, Jimmy Webb’s songs are sung by many artists, but he is not mainly known as the singer. Therefore, he is not listed here.)
It is difficult to compare some of the more recent singer-songwriters with those in the past. It is also true that in the US, we may not know many of the wonderful foreign songwriters. I have not generally included Indie singer-songwriters, country, or R&B genres. I am not as familiar with those and chose not to include them in this list. At the end, I will put an additional list of important singer-songwriters I like. Those are in no particular order.
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OK. Before I begin, a special note about John Lennon and Paul McCartney. With George Harrison, Ringo Starr, and George Martin I consider them in a class by themselves.
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The 20 25 Greatest Singer-Songwriters
With all that said, here is my humble attempt to list The Top 20 25 Greatest Singer-Songwriters (of All Time). I have also included a favorite song of mine from each writer.
25. Don McLean
“American Pie” was released in 1971 and was the number-one US hit for four weeks in 1972.
24. Jane Siberry
“Love Is Everything” from the 1993 album When I Was a Boy.
23. Elvis Costello
“All This Useless Beauty” from the 1996 album of the same name.
22. Chris Rea
“Fool (If You Think It’s Over) was released in 1978 and appears on his album Whatever Happened to Benny Santini? Also, “Last Train” from Road Songs for Lovers.
21. Janis Ian
“Stars” was written in 1971 and is on her 1974 album of the same name.
20. Jim Croce
“Operator” was the second single released from his album You Don’t Mess Around with Jim (April 1972).
19. Harry Chapin
Released in October 1974, “Cat’s in the Cradle” is Chapin’s only number-one song.
18. John Cougar Mellencamp
“Pink Houses” was released in October 1983 on his album Uh-Huh.
17. Gordon Lightfoot
“If You Could Read My Mind” reached No. 1 on the Canadian Singles Chart in 1970. He signed with Warner Bros./Reprise in 1970 and had a major hit with this song which sold over a million copies by early 1971. An interesting tidbit about him: In 1958 he moved to California to study jazz composition and orchestration for two years. To support himself he sang on demos and wrote, arranged, and produced commercial jingles.
16. Jimmy Buffett
“Son of a Son of a Sailor” is the opening track of his 1978 album of the same name.
15. Jackson Browne
He wrote “These Days” when he was 16 years old. It was first recorded by Nico in 1967 for her album Chelsea Girl.
14. Stevie Wonder
“You Are the Sunshine of My Life” from his 1972 album Talking Book.
13. Sting
“Fragile” from the 1987 album . . . Nothing Like the Sun.
12. Carole King
“You’ve Got a Friend” was written in 1971 and is on her second studio album Tapestry. James Taylor’s version reached number 1 on the Billboard Hot 100.
11. Van Morrison
“Moondance” is from his third studio album of the same name and released in January 1970.
10. Neil Young
“After the Gold Rush” is the title song from his 1970 album of the same name.
9. Billy Joel
He wrote “And So It Goes” in 1983 but did not released the song until six years later. It was on his 1989 album Storm Front. The song was inspired by the Scottish ballad “Barbara Allen.” It is in iambic tetrameter and is a simple melody accompanied by piano. A “Boston Legal” episode featured this song. “Piano Man” was his first single in North America. It is on his 1973 album Piano Man.
8. Bruce Springsteen
“Dancing in the Dark” was the first single from his 1984 album Born in the USA.
7. James Taylor
“Carolina in My Mind” is from his self-titled debut album in 1968.
6. Joni Mitchell
“Chelsea Morning” is on her second album Clouds released in 1969.
5. Leonard Cohen
“Bird on the Wire” is one of his signature songs. It was recorded in September 1968 and included on his 1969 album Songs from a Room.
4. Paul Simon
He wrote “The Sound of Silence” in 1963 and 1964. Simon & Garfunkel recorded the acoustic version in March 1964 and is on their debut album Wednesday Morning, 3 A.M.
3. Randy Newman
He wrote “Feels Like Home” for his musical Randy Newman’s Faust in 1995.
2. Tom Waits
“Soldier’s Things” is from his eighth studio album Swordfishtrombones (1983).
1. Bob Dylan
“Mr. Tambourine Man” was the first track on his album Bringing It All Back Home released in March 1965.
Honorable Mentions (in no particular order):
Joan Baez
“Diamonds and Rust” was written in 1974 and released in 1975. The song is regarded by many as one of her best compositions. The song alludes to her relationship with Bob Dylan ten years before that, although he is not specifically named in the song.
Dan Fogelberg
“Same Old Lang Syne” was released as a single in 1980 and appeared on his 1981 album The Innocent Age.
John Prine
“Angel from Montgomery” was on his self-titled 1971 album John Prine.
Woody Guthrie
“This Land Is Your Land” was written in 1940. Guthrie is considered to be one of the most significant figures in American western folk music. His music has influenced generations of songwriters.
Steve Goodman
“City of New Orleans” song was a hit for Arlo Guthrie in 1972. The song has been covered by such artists as: Willie Nelson, Johnny Cash, Judy Collins, and Hank Snow—to name a few. Steve won a posthumous Grammy Award for Best Country Song in 1985 for Willie Nelson’s version.
Pete Seeger
“Turn! Turn! Turn!” was written in the late 1950s and first recorded in 1959. Except for the title, the lyrics of the first eight verses are from the third chapter of the Book of Ecclesiastes. The song became an international hit in 1965 when it was recorded by the Byrds.
Prince
Christopher Cross
John Sebastian
Bob Seger
Steve Winwood
Rick Nelson
David Crosby
Stephen Stills
Graham Nash
Robert Johnson
Willie Nelson
Johnny Cash
Hank Williams
Dolly Parton
Guy Clark
Taylor Swift
Harry Nilsson
Bruce Hornsby
Townes Van Zandt
Lou Reed
David Bowie
Eric Clapton
Elliott Smith
Norah Jones
Chuck Berry
John Denver
Kenny Loggins
Kris Kristofferson
Neil Diamond
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Who are your favorite singer-songwriters? Let me know in the comments!
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