The 100 saddest songs

The 100 saddest songs, according to Adam Brent Thoroughgoing, author of 

This Will End in Tears: The Miserableness Guide to Music:

1. “Adagio for Strings,” Samuel Barber

2. “Strange Fruit,” Billie Holiday

3. “In Darkness Let Me Dwell,” John Dowland

4. “Marie,” Townes Van Zandt

5. “Rank Stranger,” The Stanley Brothers

6. “I’m So Lonesome I Could Cry,” Hank Williams

7. “Only the Lonely,” Frank Sinatra

8. “Nothing Compares 2 U,” Sinead O’ Conner

9. “Caroline, No,” The Beach Boys

10. “DP 1.1,” William Basinski

11. “Tennessee Waltz,” Patti Page

12. “Last Night I Dreamt That Somebody Loved Me,” The Smiths

13. “Dark Was the Night, Cold Was the Ground,” Blind Willie Johnson

14. “Dido’s Lament,” Henry Purcell

15. “Holocaust,” Big Star

16. “Auld Lang Syne,” Guy Lombardo

17. “Who Knows Where the Time Goes,” Nina Simone

18. “Past, Present and Future,” The Shangri-Las

19. “The Last Letter,” Rex Griffin

20. “Gloomy Sunday,” Björk

21. “Sometimes I Feel Like a Motherless Child,” Paul Robeson

22. “I Wish My Baby Was Born,” Dillard Chandler

23. “Not Dark Yet,” Bob Dylan

24. “Alabama,” John Coltrane

25. “You Forgot to Answer,” Nico

26. “Der Abschied (The Farewell),” Gustav Mahler

27. “Taps,” Daniel Butterfield

28. “Crying,” Roy Orbison

29. “Hurt,” Johnny Cash

30. “Hallelujah,” Jeff Buckley

31. “St. “James Infirmary Blues,” Louis Armstrong (1959 Recording)

32. “He Stopped Loving Her Today,” George Jones

33. “Song to the Siren,” This Mortal Coil

34. “Mille Regretz,” Josquin des Prez

35. “The Dark End of the Street,” James Carr

36. “Ne Me Quitte Pas,” Jacques Brel

37. “Shipbuilding,” Robert Wyatt

38. “Highway Patrolman,” Bruce Springsteen

39. “My Mom,” Chocolate Genius

40. “Lush Life,” John Coltrane and Johnny Hartman

41. “The Same Deep Water as You,” The Cure

42. “Hope There’s Someone,” Antony and the Johnsons

43. “Remember My Forgotten Man,” Joan Blondell, Etta Moten

44. “How to Disappear Completely,” Radiohead

45. “How Can You Mend a Broken Heart,” Al Green

46. “Dies Irae,” Thomas of Celano

47. “Dress Rehearsal Rag,” Leonard Cohen

48. “The Blizzard,” Jim Reeves

49. “Your New Friend,” Smog

50. “Cocktails,” Dennis Wilson

51. “I See a Darkness,” Bonnie “Prince” Billy

52. “I’ve Been Loving You Too Long,” Otis Redding

53. “Dry Your Eyes,” The Streets

54. “Hymne A L’amour (Hymn to Love),” Edith Piaf

55. “Lorena,” Rev. Henry D. L. Webster, Joseph Philbrick Webster

56. “The End of the World,” Skeeter Davis

57. “Sadness,” Ornette Coleman

58. “Our Song,” Joe Henry

59. “Feel Like Going Home,” Charlie Rich

60. “Te Recuerdo Amanda (I Remember You, Amanda),” Victor Jara

61. “Der Liermann (The Hurdy-Gurdy Man),” Franz Schubert

62. “I (Who Have Nothing),” Ben E. King

63. “Brother, Can You Spare a Dime?,” Bing Crosby

64. “Tank Park Salute,” Billy Bragg

65. “Trouble of the World,” Mahalia Jackson

66. “The Electrician,” The Walker Brothers

67. “Con Onor Muore (To Die With Honor),” Giacomo Puccini

68. “The Band Played Waltzing Matilda,” The Pogues

69. “Lonesome Town,” Ricky Nelson

70. “On the Nature of Daylight,” Max Richter

71. “Goodbye Pork Pie (Theme for Lester Young),” Charles Mingus

72. “Blue in Green,” Miles Davis

73. “Everybody Hurts,” R.E.M.

74. “Adagio in G Minor,” Tomaso Albonini

75. “Borrowed Tune,” Neil Young

76. “River,” Joni Mitchell

77. “Twilight,” Elliott Smith

78. “The Colour of Spring,” Mark Hollis

79. “Cantus in Memory of Benjamin Britten,” Arvo Pärt

80. “Blue and Grey Shirt,” American Music Club

81. “Stay With Me,” Lorraine Ellison

82. “100,000 Fireflies,” The Magnetic Fields

83. “Symphony No. 3 (Symphony of Sorrowful Songs): Third Movement,” Henryk Mikolaj Górecki

84. “The Kids,” Lou Reed

85. “Prelude No. “4 in E Minor,” Frédéric Chopin

86. “I Wish It Would Rain,” Johnny Adams

87. “Withered and Died,” Richard and Linda Thompson

88. “Sam Stone,” John Prine

89. “Blemish,” David Sylvian

90. “The Shortest Story,” Harry Chapin

91. “Suicide is Painless (Theme From M*A*S*H*),” Johnny Mandel, Mike Altman

92. “Fruit Tree,” Nick Drake

93. “Katy Song,” Red House Painters

94. “Wish You Were Here,” Pink Floyd

95. “Sour Times (Live),” Portishead

96. “Someone Like You,” Adele

97. “Death Letter,” Son House

98. “Mr. Blue,” The Fleetwoods

99. “The Ballad of Lucy Jordan,” Marianne Faithfull

100. “The Sun’s Gone Dim and the Sky’s Turned Black,” Jóhann Jóhannsson