Singer-Songwriters: The 100 Greatest Songs

In a time long ago – well, sometime before the early 60s – songwriters wrote songs and singers sang them. It was less often that people did both. Of course, there were exceptions; arguably it was the coming of Bob Dylan that signalled a great leap forward for singer-songwriters.

But, cast your mind back, if you can, to March 1962 and the release of Dylan’s self-titled debut album. Of the 13 songs on the album, just two were written by the Bobster. Five were Dylan’s arrangements of traditional songs, two were other people’s arrangements of traditional songs, and there were covers of Blind Lemon Jefferson, Jesse Fuller, Bukka White and Curtis Jones. It wasn’t until a year later, in May 1963, that Bob’s second album revealed his emerging songwriting talents: 11 of its 13 tracks were Dylan originals. Two months earlier and Lennon and McCartney wrote eight of the 14 tracks on The Beatles’ debut album. It was something of a turning point.

Dylan came out of the folk tradition, and it was the acoustic-folk genre that was – and remains – the spiritual home of the singer-songwriter, where performers tend to provide the sole accompaniment to an entire composition or song, typically using a guitar or piano. The political protest songs of Pete Seeger and Woody Guthrie are what people thought of as singer-songwriters before Dylan, but by 1963 there was a subtle shift that accelerated as the 60s advanced. Even before that time, however, singers such as Hank Williams were forging a place in musical history where they wrote and performed their own songs, though they were often backed by a group, which causes some to forget that Williams was a true singer-songwriter.

Go back a little further and Blind Lemon Jefferson, Blind Willie McTell, Son House and others from the Mississippi Delta were doing just the same in the 30s. Add to that list Robert Johnson, who created a canon second to none of songs that have been covered by countless others ever since. But at the same time, never forget that when Johnson was playing juke joints and house rent parties, he would frequently cover the hits of Bing Crosby who was singing songs from the writers that frequented New York’s Tin Pan Alley. He, like so many performers, was trying to entertain and earn a crust… the covers band and covers singer is a proud tradition. Recently someone posted a video online of a guy with a guitar covering Stevie Wonder’s ‘Superstition’ on stage at a hotel, somewhere in America; Stevie himself was in the hotel and he went on stage to join the unknown performer to sing his own composition. Somehow it feels like the tradition finally came full circle.

We have tried to come up with the ultimate playlist of the greatest songs performed and written by singer-songwriters. It includes all the usual suspects, From Dylan, Elton and Stevie to Carole King, Joni and Dolly. It also unearths some real gems by singer-songwriters who have crafted superb songs that forced their way into our list.

There’s Scott Walker’s ‘Such A Small Love’, from his debut solo album; one of Canada’s finest songwriter-singers, Gino Vannelli and ‘Gypsy Days’ Nashville’s Gretchen Peters’ ‘Secret Of Life’, Clifford T Ward’s ‘Home Thoughts From Abroad’ and Stephen Bishop’s ‘On and On’. Which is just what we could do with this list… The 70s was the heyday of the singer-songwriter, but they are as meaningful today as they’ve ever been.

So what are the 100 greatest songs?

100. Skin – Rag’n’Bone Man

99. This Masquerade – Leon Russell

98. Perfect Day – Lou Reed

97. Okie From Muskogee – Merle Haggard

96. Fidelity – Regina Spektor

95. Actor Out Of Work – St. Vincent

94. Lonely At The Top – Randy Newman

93. Suedehead – Morrissey

92. Southern Nights – Allen Toussaint

91. Chicago – Sufjan Stevens

90. Drop The Pilot – Joan Armatrading

89. Fast Car – Tracy Chapman

88. Luka – Suzanne Vega

87. The Last Living Rose – PJ Harvey

86. Wild World – Yusuf/Cat Stevens

85. Everything Is Everything – Ms. Lauryn Hill

84. Werewolves of London – Warren Zevon

83. Cornflake Girl – Tori Amos

82. Land Locked Blues – Bright Eyes

81. Fast As You Can – Fiona Apple

80. Sailing to Philadelphia – Mark Knopfler

79. Fist City – Loretta Lynn

78. Record Year – Eric Church

77. Traveller – Chris Stapelton

76. Merry Go ‘Round – Kasey Musgraves

75. Royals – Lorde

74. Downtown Train – Tom Waits

73.  Where I Stood – Missy Higgins

72. Perfect Skin – Lloyd Cole and the Commotions

71. If It Makes You Happy – Sheryl Crow

70. Free Fallin’ – Tom Petty

69. Going To A Town – Rufus Wainwright

68. Capsized – Andrew Bird

67. American Pie – Don McLean

66. Miss Misery – Elliot Smith

65. For A Change – Chris Difford

64. Maggie May – Rod Stewart

63. On and On – Stephen Bishop

62. Being With You – Smokey Robinson

61. Garden Party – Rick Nelson, The Stone Canyon Band

60. Draw Of The Cards – Kim Carnes

59. The Immigrant – Neil Sedaka

58. Home Thoughts From Abroad – Clifford T. Ward

57. Superstition – Stevie Wonder

56. Life On Mars – David Bowie

55. Song To The Siren – Tim Buckley

54. New Kid In Town – JD Souther

53. The End of Innocence – Don Henley

52. Desperados Waiting For A Train – Guy Clark

51. Boulder To Birmingham – Emmylou Harris

50. She – Gram Parsons

49. Sunday Mornin’ Comin’ Down – Kris Kristofferson

48. Copperhead Road – Steve Earle

47. 1952 Vincent Black Lightning – Richard Thompson

46. The Wreck of Edmund Fitzgerald – Gordon Lightfoot

45. Cat’s In The Cradle – Harry Chaplin

44. Oh My Sweet Carolina – Ryan Adams

43. Chateau Lobby #4 (in C for Two Virgins) – Father John Misty

42. Lost Cause – Beck

41. Sweet Caroline – Neil Diamond

40. Piano Man – Billy Joel

39. On The Road Again – Willie Nelson

38. Wuthering Heights – Kate Bush

37. Rollin’ And Tumblin’ – Muddy Waters

36. Alison – Elvis Costello

35. Let’s Get It On – Marvin Gaye

34. Solid Air – John Martyn

33. Come Away With Me – Norah Jones

32. Jolene – Dolly Parton

31. Your Cheatin’ Heart – Hank Williams, Drifting Cowboys

30. Longer – Dan Fogelberg

29. At Seventeen – Janis Ian

28. Like A Rolling Stone – Bob Dylan

27. The Secret of Life – Gretchen Peters

26. We’re All Alone – Boz Scaggs

25. Gypsy Days – Gino Vannelli

24. Running On Empty – Jackson Browne

23. Pink Moon – Nick Drake

22. Lady-O – Judee Sill

21. Traction In The Rain – David Crosby

20. Fire and Rain – James Taylor

19. Yesterday – Paul McCartney

18. On The Border – Al Stewart

17. Into The Mystic – Van Morrison

16. Field of Gold – Sting

15. Suzanne – Leonard Cohen

14. Heart of Gold – Neil Young

13. Such A Small Love – Scott Walker

12. How Can We Hang On To A Dream – Tim Hardin

11. 50 Ways To Leave Your Lover – Paul Simon

10. Late Night Grande Hotel – Nanci Griffith

9. Constant Craving – k.d. lang

8. Both Sides Now – Joni Mitchell

7. My Sweet Lord – George Harrison

6. Stony End – Laura Nyro

5. You’re So Vain – Carly Simon

4. Imagine – John Lennon

3. It’s Too Late – Carole King

2. Your Song – Elton John

1. Who Knows Where The Time Goes – Sandy Denny

Format: UK English