BEST ONE HUNDRED SONGS TO BREAK YOUR HEART, MAKE YOU SAD, CRY.

We need a list like this, because songs do assault the heart, and the two most readily accessible lists we find on the web of “songs that make you cry” are so-so, mostly devoted to recent and mediocre indie rock songs.

The “songs that make you cry” lists are further limited by a lame criterion of a close-reading of lyrics—many people don’t know this, but this song is really about a friend of a friend of the songwriter who was dying of cancer, etc.

A great sad song should strike one as sad immediately, by itself, on its own, with its own poetry and music and mood—it should not require an actual sad reason why it was composed revealed to the listener—one shouldn’t need to have the lyrics explained in order to be saddened by the song.

And yet, and yet…secret sad meanings hidden in the lyrics…okay, who can resist those?

But here’s the deal: First, if the actual tragedy the lyrics allude to is the source of the heart-breaking song, then how is this any different than if someone simply told you of a heart-breaking tragedy?

Second, it is the discovery of the hidden aspect in the lyrics which does most of the heart-breaking work, for it is this ‘finding out’ which imitates the mechanics of regret: oh if I had only known how much they really loved me! It is this dynamic which is at work in the oh this is what the song means! trick.

Whether the song is about something that actually happened is beside the point. If we are really moved by a song, on some level it is real for us—and nothing more needs to be said on the issue.  Obviously, the point is, when compiling this list, we have considered the total impact on the heart by the song itself. The tragedy (imagined or real) matters, obviously, but more importantly is how it all comes together in the way it is conveyed by the song, so it stays pleasantly in our memory. The melting of the heart by a song (whether “tragic” or not) should be a pleasant experience. Bewitching perhaps, but ultimately a pleasure, since happiness is (or should be) the end of existence. The songs on our list may, or may not, make you cry. But it should be a happy cry.

But the more we ponder this whole question of context, the more it threatens to explode the whole project: what about a song like “Un Bel Di,” from Puccini’s opera, Madame Butterfly, also known as “One Fine Day?” Does one have to know Italian, or the opera’s heart-breaking story from which the song emerges, to appreciate this song?

Well—to truly appreciate the song, yes.

“Context,” which, for the sake of “artistic purity,” we have been trying to mitigate, if not eliminate, keeps looming up, like a moon which needs to shine.

The best conclusion, we think, is this: if the moon is a really beautiful one, and is really shining beautifully—if the song itself really is magnificent—we can expect the listener to also understand the clouds heaped up around that moon—especially if the song is already deservedly popular; or, if the song itself, because of what it is, really deserves, in our opinion, this extra knowledge and attention.

We will not worry ourselves that lists like this can never satisfy everyone, for this does not mean lists such as this are not worth doing. Scarriet’s One Hundred Hippie Songs of All Time, published a year ago, is consistently visited two thousand times a week.

But of course “hippie” is more readily understood than “heart.”

And here we might as well add that the heart needs protection—and this is what T.S. Eliot meant when he famously said poetry is “an escape from emotion”—the heart-breaking song is restrained and cool and artificial to a certain degree precisely so the heartbreak doesn’t overwhelm us. But… isn’t that the point? To be overwhelmed, so the heart “melts?” Yes, but some cry at almost anything—commercials, other people crying—so that the songs on this list aren’t even necessary. Keep in mind we speak of ideal, aesthetic, and universal “melting.” This entire list, obviously, cannot be heart-breaking for you.

Further, in this list we attempt to appeal to all tastes.

The genres of hard rock and blues, the music that “sold its soul to the devil” receives its due punishment by not being included on this list. We could have picked a song like “The Thrill Is Gone” to honor the late, great B.B. King, but we could not find it in our hearts to do so. Work like this is admirable, but, for us, just not heart-melting. The stretched-out, pounding attitude of ‘ain’t life a bitch? doesn’t quite fit what we are after.

The “melting” is not finally from pity, but from the extraordinarily beautiful and wise.

Occasionally the beautifully wise is like ice—but as this list shows, icy perfection rarely melts the heart.  Often it is just a warm, slow melody.

Puccini might be said to have invented the modern pop song, or maybe it was Mozart?  Or Bach?  The hook—and then creeping behind it, another equally as sweet!  And so sweet—it has to be brief.

And then, added to the music, the story and the poetry.  What mortal can resist it?

Anyway, we hope you enjoy our latest, One Hundred Songs To Melt The Heart.

1. One Fine Day (Puccini’s Madame Butterfly Aria, “Un Bel Di,” is the heart-breaking standard: beautiful, involves a young girl’s heart—that sings the song—a sailor, and two cultures on either side of the world—and the “one fine day” never comes. 

2. Nothing Compares 2 U (Sinead O’Connor’s performance of Prince’s song proves sadness is best when it is majestic, observant—“7 hours and 15 days”—and has no bitterness. A tear-jerker for the ages. An electronic standard.)

3. Someone Like You (Adelle’s voice inhabits this Edna St. Vincent Millay-type song’s every pitch, timbre, and mood—resigned, but not resigned—almost as if her very heart were the instrument. Too recent to appreciate? No, this performance is timeless.)

4. Just Say I Love Him (Nina Simone’s six and a half minute, poignant, subtly electric guitar-soaked revery from her neglected masterpiece Forbidden Fruit—1961. If women are dominating this list so far? That’s why they call them divas, fellas…)

5. Video Games (The video of this casually, stupidly languid but passionate song by Lana Del Rey has 83 million views and yes we are in a different era now of perfecting heart-tugging—technically and artistically. A female’s hungry, proud, sultry, deeply expressive voice is still key, however.)

6. Sue Me (Duet between Frank Sinatra and Vivian Blaine.  When her voice tearfully cracks on “I could honestly die.” From Frank Loesser’s Guys and Dolls. The scene itself is semi-comic—it doesn’t matter.)

7. Hurt (Johnny Cash. Noble, yet agonizing. Tears the only defense against this.)

8. Honey (Bobby Goldsboro makes a goddamn movie with a song. Sentimental, perhaps, but the vocal and the lyrics expand possibilities in a way that practically forms a template of its own.)

9. O Mio Babbino Caro (Puccini and Callas. The song doesn’t need translation. Puccini invented pop, perhaps.)

10. There Is A Light That Never Goes Out (The Smiths. Urban, angsty poetry at its very best. The Smiths’ signature sound is divine, in a fake-casual sort of way.)

11. Stranger in Paradise (The Four Aces’ hokey-histrionic performance of this exquisite song is the formula of homely passion which is necessary; it is not icy, classical perfection we’re after. Sigh deeply if you agree.)

12. It’s All In the Game (Tommy Edwards. It’s all in this glimpsed not quite sad perfect gem of a song.)

13. Alameda (Elliot Smith almost wallows too much in self-misery to project: “Nobody broke your heart. You broke your own cause you can’t finish what you start.”)

14. Hello In There (John Prine made a masterpiece for neglected seniors.)

15. Heart of Gold (Neil Young. It’s very hard to write a truly beautiful sad song. The slightest trace of self-pity ruins it.)

16. Saint James Hospital (Pete Seeger’s Youtube ‘video’ of this beautiful, beautiful, somber, ‘dying cowboy’ folk song has only about 3,000 views. A pity.)

17. Turandot  (Puccini. Pavarotti. Music so sweet it hurts.)

18. Lacrimosa (Mozart. The Requiem. The happy genius feeling indescribable pain.)

19. Green Fields (Brothers Four. Layers of slow, trembling, lush, melancholy. Gorgeous.)

20. Wild World (Cat Stevens. An achingly sad ‘lover leaving’ song tinged with impotent fatherly advice. )

21. Blue Velvet (Bobby Vinton sings this as schmaltzy pop–the velvety tune itself transcends its setting.)

22. My Sweet Lord (George Harrison took the most powerful secular format ever: rock music, blended it with religious feelings, in a way which still sounds like a love song: “I’d really like to know you.”)

23. Auld Lang Syne (The Bobby Burns’ tear-jerker.)

24. April Come She Will (Simon and Garfunkle. We can never get enough, it seems, of lost love and seasons. A couple of guys from Queens, New York. Maybe the best singing/songwriting team ever.)

25. You’ve Got To Hide Your Love Away (The Beatles. John Lennon had this love/hate thing with the music of Bob Dylan. Lennon was a genius who hated/loved.)

26. Space Oddity (David Bowie. Alienated by technology, a theme of this great techno-song from our modern era of passionate contradictions.)

27. The Man That Got Away (Judy Garland. Ju-dy Gar-land. Man-that-got-away. Okay?)

28. The Way We Were (Barbara Streisand. Nostalgia from one of the greatest pop divas.)

29. And The Sun Will Shine (Bee Gees. Robin Gibb. Sweet. Vaguely sorrowful. That is all.)

30. I’m Not In Love (10cc. “Big boys don’t cry.” Yes, they do.)

31. If You Go Away (Shirley Bassey best performs this Jaque Brel number of what we all fear.)

32. Dream Brother (Jeff Buckley. A superbly expressed song of beautiful primal longing.)

33. High Your Love (Donovan, from his 1996 Sutras: “Looking for you in the longing of life, and all the time, you were here by my side.” Wow. It’s rare when embarrassingly wise wisdom breaks your heart.)

34. Do You Realize?? (Flaming Lips. A sentimental song that grabs sentimentality by the throat.)

35. Hey That’s No Way To Say Goodbye (Leonard Cohen. The nearly atonal baritone delivery manages to be a mesmerizing diversion. Anyone can sing. Anyone can make music. Anyone can cry.)

36. What Is A Youth (from Zefferelli’s Romeo and Juliet—also known as “A Time For Us.” This lovely song, sung as Romeo and Juliet first cavort at the home of the Capulets is a happy/sad cinematic, musical stunner)

37. Knocking On Heaven’s Door (Bob Dylan. Zimmerman was so sentimental he had to be tough.)

38. The Only Living Boy In New York (Simon and Garfunkel. It is about tall Art going off to an acting gig and leaving small Paul alone, who takes the sweetest revenge in it.)

39. It’s All Too Much (The Beatles from Yellow Submarine. A lesser known song, but it could be the best Beatles’ recording. A pounding, psychedelia of heart-melting sweetness from George.)

40. The Incest Song (Buffy St. Marie. There are tragic ballads galore; this one is quite good—from her 1964 It’s My Way! one of the greatest original folk albums—no, albums—ever recorded.)

41. Go Way From My Window (John Jacob Niles.  An old man’s heartbreaking voice. Bob Dylan would later use the title of this song as a lyric in his sad-but-slightly-snarling “It Ain’t Me Babe.”)

42. Lonesome Valley (Erik Darling. “You’ve got to cross that lonesome valley by yourself.” Lyrics, music, delivery. Easily one of the greatest recordings of all time.)

43. While My Guitar Gently Weeps (George Harrison’s third on this list! “They bought and sold you.” They did.)

44. Chasing Cars (Snow Patrol. “Would you lie with me and just forget the world?” Asked sadly and sweetly.)

45. Don’t Let The Sun Catch You Crying (Jerry and the Pacemakers. String section strains to slow down the finger-snapping beat of the sad, optimistic shimmer. “Ferry ‘Cross the Mersey” is equally as good.)

46. Your Song (Elton John was a throw-back to the Tin Pan Alley days when composers and lyricists were separate people; John wrote all the music; Bernie Taupin, the lyrics: “how wonderful life is that you’re in the world.”)

47. I’ll Be Seeing You (Billie Holiday. This is perhaps the poetic trope: seeing the beloved in other things. And Holiday’s voice is one of those sad ones we love because it talks/sings.)

48. Bridge Over Troubled Water (Simon and Garfunkel. Their album of the same name beat out Let It Be for the Grammy as the 60s came to an end, Art & Paul and the Beatles splitting up.)

49. I Think It’s Going To Rain Today (Judy Collins sings it from her magnificent 1966 covers album “In My Life.”)

50. It Was Sad When That Great Ship Went Down  (Honestly, we couldn’t find the definitive recording of this great, great folk song of the Titanic disaster. Probably Pete Seeger.)

51. Perfect Day (Lou Reed. Languid masterpiece from another artist with “a voice that came from you and me.”)

52. Lady Jane (The Brian Jones era Rolling Stones. Old people back in the 60s who hated noisy rock must have been taken aback when songs like this were produced.)

53. A Day in the Life (Beatles. The reflective, sad quietness of this song reflects the touring band, going in the studio, growing up.)

54. Walk On By (It can’t help but feel a little like Bacharach, David and Warwick is music as business. A perfect business. Imagine these three as unknowns, turning out hundreds of songs a year, and then the whole cache is discovered.)

55. Sarah (Scarrietmeister. We include our own singing, songwriting, and producing only to prove that Poe was right: only a good poet can be a good critic. We humbly write and record music, and that’s why we can sensitively and lovingly make these lists.)

56. Smile (The lyrics are iconic; the musical credit goes to Charlie Chaplin, who first sang it in his 1936 film, Modern Times. Which is how life works: you’re working on a movie and then a song comes to you…)

57. End of the World (Skeeter Davis asks “Don’t they know it’s the end of the world?” in one of the sweetest, simplest, and most poignant songs of all time.)

58. Do You Really Want To Hurt Me (The reggae beat, the bend-y notes, the hopeless, self-effacing melancholy required, perhaps, a Boy George, to make it happen; or was this song inevitable?)

59. Smoke Gets In Your Eyes (The songwriting team of Jerome Kern and Otto Harbach wrote this for their 1933 musical. Great songs are inevitably written for something…a musical, a movie, a friend, etc)

60. Moon River (Once lyricist and Georgia native Johnny Mercer put “moon” with “river, the song probably wrote itself; he originally tried “blue river,” but found it was already taken. “Huckleberry friend” worked, too.)

61. Over the Rainbow (The best songs are simple ones: “somewhere,” became for the songwriting industry what “nevermore” was for poetry; the octave jump from some to where launched us “over the rainbow.”)

62. Good Night Irene (Leadbelly learned the song in the South from family in the beginning of the 20th century. Pete Seeger with the Weavers—before Elvis—made black music for the American masses: Billboard’s no. 1 song for 1950, the year after Leadbelly died.)

63. I Will Always Love You (Written and recorded by Dolly Parton in 1973 and made into a monster hit by Whitney Houston in 1992. Both times for a movie.)

64. Come All You Fair And Tender Maids (Pete Seeger sings it best. You hear a beautiful, old, neglected folk song like this and you can’t help but wonder how easily today’s pop machine could make it a “hit.”)

65. September Song (Lotte Lenya sings this sad song written by her husband, Kurt Weil)

66. You’ve Got A Friend (Carol King wrote it and James Taylor recorded it in a comforting blast of singer/songwriter bliss.)

67. Ave Maria (Schubert. Uplifting. Can the heart follow?)

68. Are You Lonesome Tonight? (Elvis Presley was a rocker, but also country western—a genre, we are aware, that is not represented well by our list. Hank Williams moans and cries, and we won’t deny the greatness of this music, but heart-wise, it often sounds too quirky or cornball to our N’eastern ears.)

69. Sheep May Safely Graze (Kirsten Flagstad does a pretty good job with this Bach cantata.)

70. The Three Ravens (Alfred Deller sings in the “sweet and high” style this ancient English ballad about a dead knight and his faithful animals.)

71. An Affair To Remember (Nat King Cole. One of the great heart-melting singers. Beautiful, sad song from the beautiful, sad film.)

72. Is That All There It Is? (Peggy Lee gets deep.)

73. The Winner Takes It All (ABBA. Is this really true?  Is there a “winner” in love? It doesn’t matter, because the song makes it true.)

74. Where Have All The Flowers Gone? (Pete Seeger’s song, fashioned from other sources in 1955. It led to Dylan’s question “How many roads must a man walk down?” and the rest is folk/rock/pop history.)

75. Those Were The Days (Mary Hopkin. Does history kill nostalgia? The Beatles produced this.)

76. My Cherie Amour (Stevie Wonder recorded it; he and two others wrote it. Sweet, sad, pop perfection.)

77. Cry Me A River (A jazz standard embracing heartbreak for two.)

78. Another Day (Paul McCartney wrote a lot of sad, clever, touching songs; he sang this one with Linda.)

79. A Day In The Life Of A Fool (Jack Jones does a solid job with this sob-fest from Brazil. Black Orpheus is the 1959 Academy Award winning film which made the song famous.)

80. It Was a Very Good Year (Songs that look back over life are usually a pretty good bet to be at least mildly heart-breaking. Frank Sinatra is the wistful deliverer in this case.)

81. Oh What Wondrous Love Is This? (A spiritual which is similar to “Amazing Grace,” and just as good.)

82. Wish You Were Here (Pink Floyd. Syd Barrett was their songwriter, and then, after he tragically left, the subject of their best work.)

83. I Don’t Like Mondays (Boomtown Rats. A big hit in England, Bob Geldoff wrote this song in 1979 from a news story out of San Diego, California: a 16 year old girl went on a shooting spree for no apparent reason.)

84. Hey There Delilah (Plain White Ts. Songs with girls’ names are usually a good start.)

85. Indian Summer (The Doors had a bunch of haunting little numbers like this. It is argued often that Morrison was not a “real” poet, but this group used Brecht/Weil and William Blake in their recordings. They were one of the truly poetic rock groups, far more sensitive than most.)

86. Time Of Your Life (Green Day. A breakup song that doesn’t quite sound like a breakup song—the most noble kind.)

87. La Vie En Rose (Edith Piaf is the world’s favorite female French singer. This one song will have to represent the lovely French cafe tradition. Our favorite album of this type is April In Paris by Jacqueline Francois.)

88. You Are My Sunshine (First recorded in 1939; covered numerous times. Sing it to your kid.)

89. Bittersweet Symphony (The Verve. We love the video of Richard Ashcroft knocking people over in London as he lip-syncs.)

90. Viva La Vida (Cold Play. An uplifting number. The lyrics are somewhere between profound and hazy, but the song is catchy enough so one doesn’t care.)

91. It Will Rain (Bruno Mars. Perhaps the best from this visceral writer/performer. This one was co-written for a movie—“Twilight.”)

92. Careless Whisper (George Michael. Co-written with his Wham! partner when they were unknown. Sexy. Depressing. Very 80s.)

93. Come As You Are (Nirvana. Kurt Cobain generally expressed pain very well—some might feel this song is heart-breaking.)

94. Maggie May (Rod Stewart. A sad, in-love-with-an-older-woman, not-knowing-what-to-do-with-my-life song.  Doesn’t try to be a heart-breaking song, but it is.)

95. Fortunate The Man With None (Dead Can Dance. The lyrics come from a Bertolt Brecht poem.)

96. I Say A Little Prayer (Aretha Franklin sings one of the sweetest songs of all time.)

97. Nights in White Satin (Moody Blues. “Just what you want to be, you’ll be in the end” is a killer.)

98. Dear Mama (Tupac. The late rapper appreciates his mother.)

99. Everybody Hurts (R.E.M. Many songs tell stories, give advice, but not that many are written specifically to reach out and comfort.)

100. Blue (Marina and the Diamonds. Released this year; energetic and vapid, as all ‘young people’s music of today’ seems to those who are older. But it’s still about the heart.)

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