100 Saddest Songs Ever!

  1. “Tears in Heaven” Eric Clapton (1992)
  2. “He Stopped Loving Her Today” George Jones (1980)
  3. “Hurt” Nine Inch Nails (1994) | Johnny Cash (2002)
  4. “Everybody Hurts” REM (1992)
  5. “Crying” Roy Orbison (1962)
  6. “It’s Over” Roy Orbison (1964)
  7. “Alone Again (Naturally)” Gilbert O’Sullivan (1972)
  8. “Yesterday” The Beatles (1965)
  9. “If” Bread (1971)
  10. “Honey” Bobby Goldsboro (1968)
  11. “Cat’s in the Cradle” Harry Chapin (1974)
  12. “Dust in the Wind” Kansas (1977)
  13. “Last Kiss” Pearl Jam (2006)
  14. “Nothing Compares 2 You” Sinead O’Conner (1990)
  15. “Hallelujah” Jeff Buckley (1994)
  16. “Everything I Own” Bread (1972)
  17. “Mad World” Gary Jules (2003)
  18. “Eleanor Rigby” The Beatles (1966)
  19. “I’m So Lonesome I Could Cry” Hank Williams (1949)
  20. “Superstar” Karen Carpenter (1969)
  21. “Iris” Goo Goo Dolls (1998)
  22. “Memories” Elaine Paige (1983) | Barbra Streisand (1981)
  23. “Love Hurts” Nazareth (1975)
  24. “Drive” The Cars (1984)
  25. “Dance With My Father” Luther Vandross (2003)
  26. “I Can’t Make You Love Me” Bonnie Rait (1991)
  27. “Whiskey Lullaby” Braid Paisley & Alison Krausse (2004)
  28. “In The Wee Small Hours of the Morning” Frank Sinatra (1955)
  29. “Teen Angel” Mark Dinning (1959)
  30. “Goodbye to Love” The Carpenters (1972)
  31. “Sorry Seems to Be the Hardest Word” Elton John (1976)
  32. “Drugs Don’t Work” Verve (1997)
  33. “Let it Be” The Beatles (1969)
  34. “Wild World” Cat Stevens (1970)
  35. “Your Song” Elton John (1970)
  36. “She’s Leaving Home” The Beatles (1967)
  37. “Pink Moon” Nick Drake (1972)
  38. “Solitaire” The Carpenters (1975)
  39. “This Woman’s Work” Kate Bush (1990)
  40. “Concrete Angel” Martina McBride (2002)
  41. “Against All Odds” (aka “Take a Look at Me Now”) Phil Collins (1984)
  42. “I’m a Fool to Want You” Frank Sinatra (1951)
  43. “Goin’ Out of My Head” Little Anthony & The Imperials (1964)
  44. “Creep” Radiohead (1992)
  45. “Are You Lonesome Tonight?” Elvis Presley (1960)
  46. “Bright Eyes” Art Garfunkel (1979)
  47. “You Don’t Bring Me Flowers” Neil Diamond & Barbra Streisand (1978)
  48. “Candle in the Wind” Elton John (1973 & 1997)
  49. “For the Good Times” Ray Price (1970) | Elvis Presley (1972)
  50. “Annie’s Song” John Denver (1974)
  51. “Lime Tree” Bright Eyes (2007)
  52. “It’s So Hard to Say Goodbye to Yesterday” Boyz II Men (1991)
  53. “Crazy” Patsy Cline (1962)
  54. “The End of the World” Skeeter Davis (1963)
  55. “I’ll Be Missing You” P. Diddy & Faith Evans (1997)
  56. “Only the Lonely” Roy Orbison (1960)
  57. “Don’t Cry Daddy” Elvis Presley (1969)
  58. “Send in the Clowns” Judy Collins (1973)
  59. “I know It’s Over” The Smiths (1986)
  60. “In the Ghetto” Elvis Presley (1969)
  61. “Two Out of Three Ain’t Bad” Meat Loaf (1977)
  62. “My Immortal” Evanescence (2003)
  63. “Always on My Mind” Willie Nelson (1982)
  64. “Leaving on a Jet Plane” Peter, Paul and Mary (1969)
  65. “Sounds of Silence” Simon & Garfunkel (1966)
  66. “Kiss and Say Goodbye” The Manhattans (1976)
  67. “Don’t Speak” No Doubt (1996)
  68. “Asleep” The Smiths (1987)
  69. “Faithfully” Journey (1983)
  70. “I Dreamed a Dream” Susan Boyle (2009)
  71. “Total Eclipse of the Heart” Bonnie Tyler (1984)
  72. “Pictures of You” The Cure (1989)
  73. “Christmas Shoes” Newsong (1996)
  74. “Gloomy Sunday” Billie Holiday (1941)
  75. “Strange Fruit” Billie Holiday (1939)
  76. “Bring Me to Life” Evanescence (2003)
  77. “Leader of the Band” Dan Fogelberg (1981)
  78. “Imagine” John Lennon (1971)
  79. “If I Had Only Known” Reba McEntire (1991)
  80. “Butterfly Kisses” Bob Carlisle (1997)
  81. “The Tracks of My Tears” Smokey Robinson & The Miracles (1965)
  82. “I Will Always Love You” Dolly Parton (1974) | Whitney Houston (1992)
  83. “The Rose” Better Midler (1979)
  84. “The Greatest Man I Never Knew” Reba McEntire (1991)
  85. “The Way We Were” Barbra Streisand (1973)
  86. “I Fall to Pieces” Patsy Cline (1961)
  87. “I Believe (For Every Drop of Rain that Falls)” Frankie Lane (1953)
  88. “Back to Black” Amy Winehouse (2006)
  89. “Because of You” Reba McEntire & Kelly Clarkson (2005)
  90. “The Living Years” Mike & The Mechanics (1988)
  91. “No Surprises” Radiohead (1997)
  92. “Vincent” (aka “Starry, Starry Night”) Don McLean (1971)
  93. “In the Real World” Roy Orbison (1989)
  94. “Fade to Black” Metallica (1984)
  95. “Alyssa Lies” Jason Micheal Caroll (2006)
  96. “One” Metallica (1990)
  97. “Adam’s Song” Blink 182 (2000)
  98. “Danny Boy” Elvis Presley (1976)
  99. “Open Arms” Journey (1982)
  100. “With or Without You” U2 (1987)
Since the degree of sadness evoked by a song is a personal and individual experience, nearly every list of this nature is vigorously debated – based on personal tastes, experiences, and reactions to songs.
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