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

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.

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