Music Blogs

Cry Me A River: The 20 Most Heartbreaking Songs Of All Time!

Posted Thu Nov 20, 2008 5:53pm PST by The Lonely Hearts Club Banned in Rock's Backpages
For the last month Rock's Backpages has offered up a slew of sobworthy classics from all walks of pop. Country, soul, AOR, dance: you name the genre, we've scoured it for heartbreak greats. So get yer handkerchiefs ready... here's our tearjerking Top 20 , from the Everly Brothers to George Jones via Lorraine Ellison and Little Feat. --Barney Hoskyns, Rock's Backpages

20 The Everly Brothers: "So Sad (To Watch Good Love Go Bad)," from It's Everly Time (Warner Brothers, 1960) A descending scale begins a classic of sad restraint: "We used to have good times together but now I feel them slip away/It makes me cry to see love die: so sad to watch good love go bad..." Sparse backing and note-perfect harmony compliment one of Don’s greatest lyrics. The inspiration for many a tender hearted ne’r-do-well, from John Lennon to Brian Wilson and beyond.

19 The Band: "It Makes No Difference," from Northern Lights - Southern Cross (Capitol, 1975) The most artless--and most piningly desolate--love song Robbie Robertson ever wrote, sung with hopeless tenderness by Rick Danko, The Band's most artless singer. "I love you so much, and it's all I can do/Just to keep myself from telling you/That I never felt so alone before..."

18 Randy Crawford: "One Day I'll Fly Away," single (Warner Brothers, 1980) "When will love be through with me?" MOR slush to some ears, this Crusaders/Will Jennings-constructed jazz-funk-lite ballad remains irresistibly sad to many others--especially when Crawford trails off on "away" and the swelling chord drops down beneath her. Tremulous and dreamily lovely.

17 Soft Cell: "Say Hello, Wave Goodbye," single (Some Bizzare, 1982) The genius of this synthpop classic is the way it starts out as a bitchfest--Marc Almond coming on like Dusty Springfield's petulant little sister--and then suddenly flips into a deep, engulfing sadness. Even as Almond demands that his lover take her hands off him and claims that "You never knew me/I never knew you", Dave Ball's oceanic keyboard chords say the opposite--that Marc is all tetchy bravado and that this parting is bursting his heart.

16 Billie Holiday: "Don't Worry 'Bout Me," from Lady In Autumn (Verve, 1959) Billie is being so damn reasonable: "Why not call it a day the sensible way, and still be friends," she sings. And do we believe her? We do not. Her apparent acceptance that "our little show is over" cuts no ice when delivered with such cracked desperation. Truly heart-rending late Lady Day.

15 Love: "Alone Again Or," from Forever Changes (Elektra, 1967) Love’s most famous recording: written, ironically, not by leader Arthur Lee but by po' little rich boy Bryan Maclean. "I heard a funny thing, somebody said to me/‘You know that I could be in love with almost everyone/I think people are the greatest fun’. And I will be alone again tonight, my dear..." The bastard son of the Byrds meets Ennio Morricone--all West Coast harmonies, 12-string guitars and Tijuana brass--this ode to loneliness seemed to come out of nowhere in late ‘67.

14 The Pretenders: "I Go To Sleep," from Pretenders II (WEA, 1981) What a concept: a song about missing an ex-partner sung by your future ex-partner. Written by Ray Davies and sung by Chrissie Hynde, this gives a peek into the--one assumes--charred lansdscape of the Davies/Hynde relationship. A perfect marriage of arrangement (including a beautiful French horn riff), lovelorn vocals and passionate lyrics: "I was wrong, I will cry, I will love you ‘til the day I die/You alone, you alone and no-one else/You were meant for me..."

13 Dusty Springfield: "I Just Don't Know What To Do With Myself," single (Phonogram, 1964) Springfield here performs a rare feat: outperforming Dionne Warwick's own version of a Bacharach and David classic. Moving from forlorn whimper to gutsy roar, she lives the song to the full. "Going to the movies only makes me sad; parties make me feel as bad/When I'm not with you, I just don't know what to do." Decimating.

12 Little Feat: "Long Distance Love," from The Last Record Album (Warner Brothers, 1975) "Does she know she hurt me so?" How did a sad ballad get so funky and stay so sad? Lowell George was never more soulfully vulnerable than on this late-flowering gem from an otherwise indifferent Feat platter.

11 Smokey Robinson & the Miracles: "The Tracks Of My Tears," from Going To A Go-Go (Motown, 1965) Bob Dylan called Smokey "America’s greatest living poet" with good reason. The guy was able to take the most everyday images and imbue them with a real emotional strength, allowing even the flyest guy to wear his heart on his sleeve: "People say I’m the life of the party ‘cos I tell a joke or two/My smile is the make-up I wear since my break up with you..." Couple that with Marv Tarplin's peerless, aching melody and you've got the ultimate Motown heartbreaker.

10 Bonnie Raitt: "I Can't Make You Love Me," from The Luck Of The Draw (Capitol, 1991) "I'll feel the power, but you won't..." It's all very "tasty" and L.A.-musoid, this smokey ballad of resignation to loss, but it also rings hauntingly true as an articulation of honesty in the midst of misery--which makes it as much a song of healing as anything else.

9 Lorraine Ellison: "Stay With Me," single (Warner Brothers, 1966) "No, no! I can't believe!! You're leaving me!!!" The epic Bert Berns-Jerry Ragovoy ballad style taken to the outer limit, thanks in part to a borrowed Frank Sinatra orchestra. Building slowly to volcanic peaks, and laceratingly intense to the point of hoarseness, this is soul emotion at the edge of utter despair.

8 Abba: "Knowing Me, Knowing You," single (Epic, 1977) "No more carefree laughter/Silence ever after..." Not the opening lines of a Radiohead, Big Star or Jeff Buckley song, but one by those fab four Swedish moppets so beloved of the young karaoke crowd. You see, the jolly, upbeat big-hair-and-shiny-suits story of Abba hid the sadness of two failing marriages, a sadness that bubbles to the fore here. As with the Everly Brothers or Carpenters, their arrangements may be flawless and their harmonies pitch-perfect, but there’s true heartache in them there grooves.

7 Otis Redding: "I've Been Loving You Too Long," single (Volt, 1965) "You're tired, and your love is growing cold..." Good God Almighty! The prototype deep-soul howl of pitiful, nay, wretched lovesickness, sung by a big Georgia farmboy who's literally ravaged by need for his woman.

6 Sinead O'Connor: "Nothing Compares 2 U," single (Chrysalis, 1990) Forget the famous video: it's all already here in Sinead's bruised rendition--simultaneously dazed and defiant--of Prince's perfect ballad. "I could put my arms around every boy I meet..." But you know she won't.

5 The Righteous Brothers: "You've Lost That Lovin' Feelin'," single (Philles, 1964) "You never close your eyes anymore when I kiss your lips": it's got to be the second greatest opening line of any breakup song ever. (The greatest is surely from Raspberries’ ballad "Starting Over": "I used to be so f***ing optimistic til you said goodbye".) In theory it shouldn’t have worked, combining what was then almost a comedy act with Phil Spector, a man renowned for producing girl groups. Yet somehow it all came together in one of the most remarkable vocal performances of all time, with Bill Medley and Bobby Hatfield madly swapping pleas like James Brown’s Siamese twins. "Baby, baby, I’d get down on my knees for you ... If you would only love me like you used to do." Sublime.

4 Kate and Anna McGarrigle:
"Heart Like A Wheel," from Kate and Anna McGarrigle (Warner Brothers, 1975) "It's only love/That can wreck a human being and turn him inside out..." Forget Linda Ronstadt's limp cover: the sisters' original from their startling debut album simply wees all over it. Imagine Les Voix des Bulgares transplanted to Acadia, with Kate and Anna's eerie, pellucid voices blending in a meditation on love and loss that's all about a kind of mystical bewilderment. Almost supernaturally moving.

3 Frank Sinatra: "I'm A Fool To Want You," from Where Are You? (Capitol, 1957) "But then would come the time that I would neeeeeed you..." A second stab at one of the very few songs Sinatra had a hand in writing--a song born of his debilitating pain over Ava Gardner--"I'm A Fool" is the desperate sound of a Man Who Loves Too Much, who keeps going back, masochistically, to the woman who's destroyed him. One of Frank's all-time peaks.

2 Roy Orbison: "It's Over," single (Monument, 1964) "Your baby doesn't love you anymore…" (Hey, why don't you spell it out for us, Roy?) Over a rat-a-tat, execution-squad bolero beat, the Big O gives unearthly voice to what one only call terminality. Still terrifying after all these years.

1 George Jones:
"He Stopped Loving Her Today," single (Epic, 1981)
"He said I'll love you 'til I die..." Curly Putnam and Bobby Braddock wrote the shamelessly weepy lyric and melody; producer Billy Sherrill coated the track in sumptuous Nashville surround-sound; and then the greatest country singer of all gave the performance of a lifetime--a vocal imbued with deep, knee-quaking compassion for the poor schmuck who never got over the love of his life... until now, when he's "all dressed up to go away". I don't care how hard-bitten you may be, I defy you not to get a lump in the throat from this 20-year-old classic of cornball liebestod. It's utterly transcendental--the most heartbreaking record ever made.

Read more about all these artists at www.rocksbackpages.com. Over 13,000 articles by the greatest writers from the finest rock publications of the last 50 years.

6892 Comments

41. Emily -
Stairway to heaven??? How the hell do you forget a classic?

42. Yahoo! Music User -
Worst...list...ever...

43. r c -
crummy list

is this author trying to be retro or counter
intuative??

44. Misty -
gotta be I cant make u love me or stay with me my favs!

45. Fonzie -
Excuse me- "All By Myself"- Eric Carmen woulda been a WAY better choice than the ABBA song!

46. og3529 -
ok. tears in heaven by eric clapton agree all the way......

47. danielle -
what about butterfly kisses? that still makes me cry.

48. nick s -
Strangulation! by My Morning Jacket....

49. Rachel M -
These singers suck??? Holy crap if you think Frank Sinatra sucks, you're pathetic. Go back to listening to your stupid Kanye West and save the rest of us from your idiocy.
PS: Why isn't Eric Clapton's Tears in Heaven on here?

50. richietfan -
My Heart Will Go On by Celine Dion is pretty heart-breaking as well. Should be on the list.

51. Yahoo! Music User -
What about D.O.A. From Bloodrock? It's about a plane crash.

52. Irishgalgrr -
I dont like this list....where is stuff like "The Search is Over" Survivor or "Weekend in New England" (Manilow)?
Who decides these things anyway Yahoo? sheesh.

53. temme_bakayaro -
tonight i wanna cry by keith urban

54. Yahoo! Music User -
tears in heaven??????

55. EmmaA -
how about
whiskey lullaby by
alison krauss and brad paisley?

56. Sunshine -
Quit complaining about the music....Guess you do not like any songs that you can understand the words.

57. TimothyT -
CONWAY TWITTY - THATS MY JOB!!!!!!

58. JohnnyA -
this is fail

59. Autumn -
Heh, you were dead on with the number one song. He Stopped Loving her Today is byfar the most depressing song. For once I agree with you.

60. James S -
I would have added Jeff Buckley's version of Hallelujah
Page:  1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 
Leave Your Comment
You must sign in to leave a comment
Select a Blog Posts
And The Winner Is...
by Chris Willman
26
As Heard On...
by Rebecca Harper, Hulu
46
Chart Watch
by Paul Grein
141
Framed
by John Kordosh
119
GetBack
by Shawn Amos
332
Hip-Hop Media Training
by Billy Johnson, Jr.
221
List Of The Day
by Rob O'Connor
332
Maximum Performance
by Lyndsey Parker
167
Musictoob
by Justin Mathews
183
New This Week
by Dave DiMartino
123
Reality Rocks
by Lyndsey Parker
581
Rock's Backpages
by Philip Norman (1970)
191
Stop The Presses!
by Us Magazine
85
That's Really Week
by Lyndsey Parker
125
The Blender Burner
by Blender Magazine
27
The MOJO Blog
by Bill DeMain
88
The NME Blog
by Luke Lewis
49
The Spin Blog
by David Marchese
78
The Y! Music Playlist Blog
by Robert of the Radish
515
Video Ga Ga
by Lyndsey Parker
71
Viva NashVegas
by Wendy Geller
59

Pinetop Perkins' 80-year career still going

AP
Fri Nov 27, 2009 4:03am PST

AP - Noisy crowds in smoky bars don't bother 96-year-old bluesman Pinetop Perkins. It's all part of his job. Most nights, after he snuffs out his menthol cigarette, Perkins slides onto the piano bench in some club and … More »

More Music News