150 songs for sobbing on Valentine’s Day

Collected by latimesblogs

OpenheartchestscarValentine’s Day is almost here, and as everyone from your bubbe to your Facebook status won’t stop reminding you: You are alone. All alone.

Profound sadness is not for the faint of heart. And sometimes the best place to be is right in the middle of it.

Because that’s just the kind of mood we’re in. Honest. We’re not one of those toothy, gleaming motivational speakers. We’re not here to sell you a bill of goods about positive thinking and self-esteem and controlling your destiny by visualizing your chakras.

Instead, we offer 150 of the saddest songs in the world, subjectively selected and specially arranged for maximum depressive potential. And please, feel free to wallow in more anti-romance with our buddy Jason Gelt’s “Valentine’s Day songs for haters” list or recommend your own teary tunes in the comments.

1. “One More Chance” — Fairport Convention
2. “Laser Beam” — Low (or anything by Low)
3. “Drowned in My Own Tears” — Mitty Collier
4. “I See a Darkness” — Bonnie “Prince” Billy
5. “The White Lady” — Elliott Smith
6. “Down From Dover” — Dolly Parton (alternates: “Me and Little Andy” or “Jeannie’s Afraid of the Dark”)
7. “Not Gon’ Cry” — Mary J. Blige
8. “Don’t Take the Girl” — Tim McGraw
9. “Total Eclipse of the Heart” — Bonnie Tyler
10. “Casimir Pulaski Day” — Sufjan Stevens
11. “In the Wee Small Hours of the Morning” — Frank Sinatra
12. “Lost Cause” — Beck (or anything off “Sea Change”)
13. “Through My Sails” — Neil Young (alternates: “After the Gold Rush,” “Needle and the Damage Done”)
14. “The Weeping Song” — Nick Cave
15. “Kern River” — Merle Haggard (alternate: “If We Make it Through December”)
16. “She’s Out of My Life” — Michael Jackson (alternate: “Ben”)
17. “Against All Odds” — Phil Collins
18. “Gloomy Sunday” — Billie Holiday
19. “Time After Time” — Cyndi Lauper
20. “Origin of Love” — “Hedwig and the Angry Inch” soundtrack
21. “Llorando” (Crying) — Rebekah Del Rio
22. “Only You” — the Flying Pickets
23. “Nothing Compares 2 U” — Sinéad O’Connor
24. “Forever Young” — Alphaville
25. “Mad World” — Gary Jules
26. “Neither One of Us (Wants to Be the First to Say Goodbye)” — Gladys Knight & the Pips
27. “Polaroids” — Shawn Colvin
28. “Hurt” — Johnny Cash
29. “God’s Song (That’s Why I Love Mankind)” — Randy Newman
30. “The Best I Ever Had” — Gary Allan (covering Vertical Horizon)
31. “Sharin’ a Hole” — Carissa’s Weird
32. “Wish Someone Would Care” — Irma Thomas
33. “Wandering Star” — Portishead
34. “Seasons in the Sun” — Terry Jacks
35. “I Who Have Nothing” — Shirley Bassey
36. “On a Bus to St. Cloud” — Trisha Yearwood
37. “Busby Berkeley Dreams” — the Magnetic Fields
38. “Every Rose Has Its Thorn” — Poison
39. “Fake Plastic Trees” — Radiohead
40. “Thank You” — Led Zeppelin
41. “Is That All There Is?” — Peggy Lee
42. “Being in Love” — Songs: Ohia
43. “Hallelujah” — Jeff Buckley
44. “Lilac Wine” — Nina Simone
45. “If You Knew” — Neko Case
46. “Crown of Love” — the Arcade Fire
47. “Say” — Cat Power (or anything by Cat Power)
48. “Cucurrucucú Paloma” — Caetano Veloso
49. “Lonelier Than This” — Steve Earle (alternates: “Ellis Unit One” or “Over Yonder”)
50. “I’ve Been Loving You Too Long” — Otis Redding
51. “D-I-V-O-R-C-E” — Tammy Wynette
52. “Make Me a Pallet on Your Floor” — Entrance
53. “A New England” — Billy Bragg
54. “My Fair, My Dark” — Ida (covering David Schickele)
55. “November” — Tom Waits
56. “Sleep” — the Smiths
57. “Ghost” — Indigo Girls
58. “Fairytale of New York” — the Pogues
59. “Somebody” — Depeche Mode
60. “She’s Got You” — Patsy Cline
61. “Devil on my Shoulder” — Sodastream
62. “Revelator” — Gillian Welch
63. “How Can You Mend a Broken Heart” — Al Green
64. “A Cottage for Sale” — Judy Garland
65. “This Perfect World” — Freedy Johnston
66. “Untouchable Face” — Ani Difranco
67. “Goodbye” — Emmylou Harris (covering Steve Earle)
68. “Set Me Free” — Esther Phillips
69. “Tears in the Morning” — the Beach Boys (alternate: “In My Room”)
70. “Explain It to Me” — Liz Phair
71. “Why” — Annie Lennox
72. “November Rain” — Guns ‘N Roses
73. “Come Pick Me Up” — Ryan Adams
74. “In the Middle of It All” — Arthur Alexander
75. “Cats in the Cradle” — Harry Chapin
76. “So Long” — Perry Blake
77. “Verdi Cries” — 10,000 Maniacs
78. “Alone” — Heart
79. “Something I Can Never Have” — Nine Inch Nails
80. “I Can’t Hear the Music” — Loretta Lynn
81. “When a Man Loves a Woman” — Percy Sledge
82. “It’s Raining” — Quasi
83. “Can You Hear Me?” (tribute to Aaliyah & Left Eye) — Missy Elliott featuring TLC
84. “At Seventeen” — Janis Ian
85. “Never Dreamed You’d Leave in Summer” — Stevie Wonder
86. “Two-Headed Boy” — Neutral Milk Hotel
87. “The Dance” — Garth Brooks
88. “You Were Always on My Mind” — Willie Nelson
89. “Desperado” — the Langley Schools Music Project (covering the Eagles)
90. “Everybody Hurts” — R.E.M
91. “Unbreak My Heart” — Toni Braxton
92. “All I Could Do Is Cry” — Etta James
93. “Winter” — Tori Amos
94. “Who Knows Where the Time Goes” — Sandy Denny
95. “Sacrifice” — Sinead O’Connor (covering Elton John)
96. “Yesterday” — the Beatles
97. “River Man” — Nick Drake
98. “Nobody Knows You When You’re Down And Out” — Bessie Smith
99. “Wuthering Heights” — Kate Bush
100. “After You Left” — Mirah
101. “Dear Mama” — 2Pac
102. “World Without Tears” — Lucinda Williams
103. “The River” — Bruce Springsteen
104. “I Can’t Make You Love Me” — Bonnie Raitt
105. “Last Time I Saw Richard” — Joni Mitchell
106. “Just a Dream” — Carrie Underwood
107. “The Boxer” — Simon & Garfunkel
108. “Two Steps From the Blues” — Bobby Blue Bland
109. “It’s a Mother***er” — Eels
110. “I’ll Never Get Over You Getting Over Me” — Exposé
111. “To Love Is to Bury” — Cowboy Junkies
112. “The End of the Road” — Boyz II Men
113. “Lion’s Mane” — Iron & Wine
114. “Black” — Pearl Jam
115. “He Stopped Loving Her Today” — George Jones
116. “Prayers for Rain” — the Cure
117. “Dance With My Father” — Luther Vandross
118. “Sara” — Bob Dylan
119. “Tears Are in Your Eyes” — Yo La Tengo
120. “Fistful of Love” — Antony and the Johnsons
121. “$1,000 Wedding” — Gram Parsons
122. “Rainbow Connection” — Kermit the Frog
123. “Where Do You Go to (My Lovely)” — Peter Sarstedt
124. “Atmosphere” — Joy pision
125. “The Sky Is Crying’ — Elmore James
126. “Send in the Clowns” — Judy Collins
127. “Alfie” — Dionne Warwick
128. “Five String Serenade” — Mazzy Star
129. “Beautiful” — Belle and Sebastian
130. “I Don’t Want to Hear It Anymore” — Dusty Springfield
131. “Alone Again” — Jay-Jay Johanson
132. “Sittin’ on the Dock of the Bay” — Otis Redding
133. “NYC” — Interpol
134. “Poems, Prayers, and Promises” — John Denver
135. “Do I Ever Cross Your Mind?” — Linda Ronstadt, Dolly Parton, Emmylou Harris
136. “Streets of London” — Ralph McTell
137. “(Where Are You) Now That I Need You” — Don Covay
138. “Modern Romance” — Yeah Yeah Yeahs
139. “One Way Street” — Ann Peebles (“I’ve Been There Before”)
140. “Fast Car” — Tracy Chapman
141. “Courage (for Hugh MacLennan)” — Sarah Polley (covering Tragically Hip)
142. “Don’t Speak” — No Doubt
143. “Joey” — Concrete Blonde
144. “Kiss and Say Goodbye” — Manhattan
145. “Andalucia” — Mary Lou Lord (covering John Cale)
146. “Entire” — the Spinanes
147. “Till The Real Thing Comes Along” — Judy Henske
148. “I’m Not in Love” — 10cc
149. “Mercy” — Mojave 3
150. “In the Real World” — Roy Orbison

Honorable Mention
“Viva la Tristeza!” – Pedro Almodovar’s mix of songs he listened to while writing “Talk to Her”

–Elina Shatkin

Many thanks to everyone who contributed to this list: Ann Powers, August Brown, Charlie Amter, Chris Barton, Geoff Boucher, Guelda Voien, Jessica Gelt, Margaret Wappler and others.

Photo: Charles Rex Arbogast / Associated Press

9 thoughts on “150 songs for sobbing on Valentine’s Day

  1. Joe

    How could you forget Mr. gloom and doom Richard Thompson?
    Shame on you, may your tears dry up.

    The End of the Rainbow
    Al Bowlly’s in Heaven
    Waltzing’s for Dreamers
    Just to name a few.

  2. Robin

    WTF, #86? If you’re going to pick a Neutral Milk Hotel song about being alone, this is NOT the right one. Maybe Two-Headed Boy Part II? Or Oh, Comely? Or Holland 1945? Or April 8th? Or, I don’t know, maybe My Dream Girl Don’t Exist?

  3. Frederica Siebe

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