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
