Cry Me A River! The 100 Most Heartbreaking Records of All Time

AUTOR: Varios
TÍTULO: Cry Me A River! The 100 Most Heartbreaking Records of All Time
EDICIÓN: 2001
PÁGINAS:  

ARTÍCULO:
Hands up who's never been reduced to tears by a love song. There can't be many of you out there.

One of the supreme pleasures pop affords is the chance to wallow in our own pain – to hear our lovesickness framed in heartrending melodies and phrases that trigger the tearducts. Music is not just the ultimate vehicle for catharsis but the universal language of identification: I'm not the only one who ever felt this sad/bad/abandoned.

Over the following two weeks, RBP offers up a ton of sobworthy classics from all walks of pop. Country, soul, AOR, dance: you name the genre, we've scoured it for heartbreak greats.

100 Daryl Hall & John Oates: 'She's Gone', from Abandoned Luncheonette (Atlantic, 1974)
"I’m sorry, Charlie, for the imposition/ I think I’ve got the strength to carry on, but I need a drink and a quick decision..." With a wonderful conversational opening – and the full tearjerkin’ musical force of Atlantic sessionmen behind them – Daryl and John here come up with the absolute epitome of blue-eyed soul. "Everybody’s high on consolation, everybody’s tryin’ to tell me what is right for me/ And my daddy tried to bore me with a sermon. But it’s plain to see that they can’t comfort me..."
William Higham

99 John Cale: ‘(I Keep A) Close Watch’, from Music For a New Society (Island, 1982)
"I still hear your voice at night when I turn out the light and try to settle down…" Tearing at the heartstrings like a rock’n’roll Richard Burton, this is Cale at his most conventionally showbiz yet also most affecting, with his heart as his only, fragile companion.
William Higham

98 American Music Club: 'I've Been A Mess', from Mercury (Reprise, 1993)
AMC were a sensitive aberration in the macho world of ‘80s and ‘90s alternative rock. With this song, it’s AMC singer Mark Eitzel’s use of everyday language and avoidance of metaphor that makes the sentiment incredibly affecting. The way Eitzel sings "I’ve" and "you" here is about as racked-with-pain as you can get. The saddest singer’s saddest song.
William Higham

97 Bonnie Raitt: 'Too Soon To Tell', from Nick Of Time (Capitol 1989)
As J.D. Maness's pedal steel weeps gently in the background, Bonnie conspicuously fails to get to grips with desertion. Maybe one day she'll get over the hurt, learn to deal with the pain, but "right now, it's just too soon to tell..."
Mark Pringle

96 Jerry Butler: 'Make It Easy On Yourself', single (Vee-Jay, 1962)
A Burt Bacharach masterpiece given added gravitas by one of soul's greatest baritones, 'Make It Easy' is also that rare creature, the soul ballad sans recrimination – a truly magnanimous song of letting go. "Run to him… before you start crying too." The little groan Jerry lets out just before the fade is one of the most moving sounds ever emitted by a human being.
Cleothus Hardcastle

95 The Delfonics: 'Tell Me This Is A Dream', single (Philly Groove, 1972)
Recorded without the services of former svengali producer Thom Bell (who was by then producing The Stylistics), this is psychedelic soul at its trippiest, with flute and fake-sitar effects. Hart’s demented falsetto request that "somebody please tell me this is a dream" sounds like it might refer to a drug trip, but he explains in a spoken middle eight that "You know, I’m just like a guy right now that don’t wanna face the reality of the one I love leaving me".
William Higham

94 Spiritualized: 'Broken Heart', from Ladies and Gentlemen, We Are Floating in Space (Dedicated, 1997)
"And I'm crying all the time/I have to keep it covered up with a smile." Grief beyond consolation: imagine a lovelorn junkie, wrapped in hymnal Brian Wilson chords, shrouded in strings and Jimmy Webb horns, and you've got the pivotal ballad on Jason Pierce's heartbreak masterpiece.
Djuna Parnes

93 Dionne Warwick: 'Walk On By', single (Scepter, 1964)
"If you see me walking down the street, and I start to cry..." You just know that the street in question is East 82nd at Park Avenue: there's something essentially uptown, so very Manhattan, about this Bacharach and David classic. Warwick's icy cool delivers the emotional punch without fuss and palaver.
Mark Pringle

92 Percy Sledge: 'It Tears Me Up', single (Atlantic, 1966)
If Dionne Warwick is soul's vox urbana, then Percy's her down-home antithesis, and the street where he meets his ex-lover with another man is more Main Street, Sheffield, Alabama than Gotham's Upper East Side. Don't know about him, but this sure tears me up.

91 Slapp Happy: 'Scarred For Life', from Ça Va (V2, 1998)
"You can do it with kindness, keener than a knife…" The erudite trio of Dagmar Krause, Peter Blegvad and Anthony Moore reassembled for a woefully overlooked album three years ago, and this exquisite track was its opening salvo.
Djuna Parnes

90 Don Covay: 'Leave Him, Pt. 1', from Super Dude, Vol. 1 (Mercury, 1973)
"If you don't want his love…" Did the cheatin' soul-ballad genre ever produce anything as tender, as sweetly anguished as this classic falsetto deepie, cut and triple-tracked in Muscle Shoals by the man from whom Michael Phillip Jagger copped his whole vocal style?
Cleothus Hardcastle

89 Johnny Adams: 'Lonely Man', from Heart & Soul (Charly)
Boy, is he ever one lonely man. Louisiana's greatest falsetto whoops and shrieks over this fabulous Mac Rebbenack-penned ballad like his life depended on it. It probably did.
Mark Pringle

88 Eddie Hinton: 'Hard Luck Guy', from Hard Luck Guy (Capricorn, 1998)
"I'm a hard luck guy/I can't seem to get a grip on this love…" The white Otis Redding (or should that be the beige Bobby Womack?) shreds his vocal cords and tears our hearts out with this bereft, anguished wail from the pit of lovesickness – proof positive that deep Muscle Shoals soul lived on into the '90s.
Ed Doheny

87 Chic: 'I Want Your Love', from C'est Chic (Atlantic, 1978)
"All alone in my bed at night/I hug my pillow and squeeze it tight…" Not every heartbreak classic is slow and gut-churning: some of them you can even dance to. This is as funky as anything Nile'n'Nard ever did, but it's also shot through with pure, unrequited longing – the elegantly melancholy streak that helped Chic reach the parts of which other "disco" acts only dreamed.
Cleothus Hardcastle

86 Peter Hammill: ‘The Birds’ from The Love Songs (Virgin, 1984)
Hammill’s eclecticism, odd dress-sense and dodgy prog-rock roots put many off, but he’s recorded some uncompromising songs in his time. (Why else would the young John Lydon have been a fan?) A bleak meditation on the speed with which love withers ("Two days ago a girl I thought I loved suddenly didn’t seem to matter at all") ‘The Birds’ is also a beautifully sustained metaphor. "Spring came early this year... now the birds don’t know which way to sing and, my friend, neither do I…"
William Higham

85 John Edwards: 'I'll Be Your Puppet', from John Edwards (Aware, 1973)
"You know folks say that a man's supposed to be a man/But I've come too far with you, girl, to start all over again…" The sometime Detroit Spinner gives one of the all-time great vocal performances in soul on this heart-shredding mid-tempo ballad from the pen of the great Sam Dees. Agony as aural orgasm, peaking in a falsetto shriek that'll curdle your blood.
Cleothus Hardcastle

84 Jimmy Webb: 'If These Walls Could Speak', from Ten Easy Pieces (Guardian, 1996)
A record crying out to have "unashamedly slushy" stamped across its forehead… but so what. No one does schmaltz more poignantly than Webb, and this immaculate song of loss and regret is as poignant as it gets. Plus anyone who reckons the man's songs are always sung better by others should listen to the way Jimmy phrases "cold and blind and weak…"
Ed Doheny

83 Aaron Neville: 'I Love Her Too', from the original soundtrack album Heartbeat (A&M, 1983)
This Jack Nitzsche-produced gem got lost in a soppy flick about Kerouac and Neal Cassady, but it's an immaculate vehicle for the supernal falsetto of doo-wop archangel Neville (right), who multi-tracks himself over piano triplets and strings as he addresses the age-old theme of becoming hopelessly smitten with your best friend's gal. "And when this song is over, she'll be going home with you…"
Cleothus Hardcastle

82 Abba: 'Lay All Your Love On Me', single (Epic, 1981)
Set to an atypical four-on-the-floor Eurostomp, this late Abba classic is a disco hymn of forlorn devotion – as touching and rapturous in its dread as 'Knowing Me, Knowing You'. "Cause everything is new, and everything is you/And all I've learned has overturned/What can I do?"
Melody Nelson

81 Rose Royce: 'Love Don't Live Here Anymore', single (Whitfield, 1978)
Singer Gwen Dickey is one pissed-off gal here. "You've abandoned me; love don't live here anymore," she snarls, her vinegary voice suiting the lashings of bitterness this song contains. Jeez, you almost feel sorry for the bounder.
Mark Pringle

80 Jackie Wilson: 'Doggin' Around', single (Brunswick, 1960)
"You keep me so upset, my head's in a whirl…" The sickly-sweet backing-vocals notwithstanding, this is arguably Jackie's finest few minutes – jealousy given heartrending voice in a flurry of melismatic notes.
Cleothus Hardcastle

79 Todd Rundgren: 'Hurting For You', from Hermit of Mink Hollow (Bearsville, 1978) 
From the bleak romantic side of Todd (Runt, Something/Anything), rather than the wacky prog side (A Wizard/A True Star, Todd), ‘Hurting For You’ fits neatly into the ‘She Loves You’ and ‘Your Ex-Girlfriend Told Me’ school of sympathetic-boy-observing-unnecessary-heartache-of-good-friend: "I just saw the one you left behind yesterday/And I could tell that he was hurting for you..."
William Higham

78 Sandy Denny: 'I'm A Dreamer', from Rendezvous (Island, 1977)
"And the truth is, I don't think I'll ever go…" Over windswept strings and majestic piano chords, the great lost chanteuse of Britfolk pours out rich legato lines that take the breath away – a flood of passion captured for eternity a year before Denny's dreadful death.
Ed Doheny

77 Maxayn: 'I Cried My Last Tear', from Bail Out For Fun (Capricorn, 1974)
Fabulously obscure soul combo wail chilling I-will-survive statement over melodramatic piano, mellotronic strings and gloopy Moog bass. "Then I hid myself inside and walked away…" A lost classic.
Cleothus Hardcastle

76 Ann Peebles: 'I Can't Stand The Rain', single (Hi, 1973)
"...'gainst my window, bringin' back sweet memories." You can almost see La Peebles, gazing out over a bleak mid-winter East Memphis city-scape, remembering how it was "when we were together." The edge in her voice conveys anger and hurt in equal measure.
Mark Pringle

75 The Byrds: 'Set You Free This Time', from Turn! Turn! Turn! (Columbia, 1965) 
Jefferson Airplane’s Marty Balin and the Byrds’ Gene Clark were the West Coast’s most underrated balladeers, creating perfectly observed snapshots of ‘60s life. This is one of Clark’s best: a role reversal song where the heartbreaker gets her heart broken. "Now who’s standing at the door, remembering the days before and asking ‘Please be kind’ ? ... Now who’s wondering what has changed and why it cannot be arranged to have each thing work fine ?"
William Higham

74 Charlie Rich: 'Feel Like Going Home', B-side of single (Epic, 1973)
The White Negro of countrypolitan soul, Rich is Elvis, Joe Simon and Dan Penn in one despairing Memphis tenor. The gospel-sorrowful ballad Rich wrote after reading Peter Guralnick's tome of the same name isn't woman-specific but it is deeply sad, and it's hard not to surmise that "home" here is simply a euphemism for death. "Cloudy skies are closing in, and not a friend to help me…"
The Rev. Al Friston

73 Ray Pollard: 'The Drifter' (United Artists, 1965)
"I see lovers pass me by/I watch them all with a tear in my eye…" A classic of uptown Gotham soul, Pollard's brief moment in the spotlight is as harrowing an expression of loneliness as anything in pop music – this is what it feels like to be on the outside of everything, consigned to society's margins. Features one of the most lacerating cries in all of soul.
Cleothus Hardcastle

72 Bobby Bland: 'Too Far Gone', from Get On Down with Bobby Bland (ABC, 1976)
When the Grand Ole Opry-influenced Bland (right) finally got around to cutting a "country" album, this Tammy Wynette ballad was its standout song – though it's not to be confused with the 1965 Duke side 'I'm Too Far Gone (To Turn Around)', itself a Heartbreak Classic. Few recordings have ever matched 'Too Far Gone''s invocation of love that's somehow crossed the line from passion to infection – with no turning back, no possible recovery. "I guess I've been loving you too much, for too long…" It also happens to be one of BBB's most ineffably perfect vocal performances.
Barney Hoskyns

71 Jeff Buckley: 'Last Goodbye', from Grace (Columbia, 1994)
"Did you say, 'No, this can't happen to me'?" The fruit of Tim's loins goes deep and dark for the death throes of a love affair – complete with sub-'Kashmir' touches. Heady stuff.
Djuna Parnes

70 Loleatta Holloway: 'Cry To Me', from Cry To Me (Aware, 1975)
"And if you're falling down, and you can't seem to stay off the ground…" Long before she became a dancefloor diva, La Holloway was singing heartrending ballads like this, with its moist spoken intro and silky sheen of strings. Peerless heartbreak soul from the pen of Sam Dees.
Cleothus Hardcastle

69 Derek & the Dominos: 'Layla', from Layla and Other Assorted Love Songs (Polydor, 1971) 
Copycat blues riffs and support for Enoch Powell never endeared us to anyone, but both song and performance here are touched with genuine greatness. Perhaps it’s because the song seems torn out of Clapton rather than covered by his usual mask of dispassion. Written about his love for George Harrison’s missus Patti Boyd and featuring Georgia boy Duane Allman on slide, 'Layla' is one of the few heartbreakers you can also play air guitar to.
William Higham

68 David Ackles: ‘Down River', from David Ackles (Elektra, 1968)
"Times change, times change, I know it/But it sure goes slowly downriver, when you’re locked away…" Cult hero Ackles has a voice like oak-matured whisky, at once fragile and uncompromising. Backed by grand piano and Hammond organ, Ackles here takes on the role of a newly released ex-con so excited to meet his old girlfriend Rosie only to find out that she has married his best friend Ben. 
William Higham

67 Joy Division: 'Love Will Tear Us Apart', single (Factory, 1980)
"Why is the bedroom so cold?/Turn away on your side…" Despite its whiteboy new-romo shoulder-dance beat and the disembodied sub-Sinatra croon of Ian Curtis' vocal – or maybe because of those very things – 'LWTUA' remains a chilling heartbreak classic 21 years after its release. (And was the discreet echo of 'And Then He Kissed Me' a Martin Hannett joke?)
Djuna Parnes

66 Lewis Taylor: 'Satisfied', from Lewis II (Island, 2000)
"Baby, I could say I'm over this/But I know very well I'll never have my fill…" Gypsy soulboy Taylor really pushes the boat out on this epic of pining loss – of ecstatic grief – climaxing as it does in a mind-splitting guitar blowout. Imagine Smokey Robinson singing Todd Rundgren's 'The Last Ride' and you're halfway there.
Barney Hoskyns

65 The Band: 'The Unfaithful Servant', from The Band (Capitol, 1969)
Narrator Rick Danko has been sent away by his lover for some unspecified misdemeanour. His self-regarding, third-person insouciance ("you take it like a grain of salt") is undercut by the raw first-person pain as he says "goodbye to my country home, so long to the lady I have known." An extraordinarily complex song to which a paragraph like this will never do justice.
Mark Pringle

64 Al Green: 'I'm So Lonesome I Could Cry', from Call Me (Hi, 1973)
If the Hank Williams original is a cryin'-in-your-beer classic, the Rev. Al's take on it is an entirely bleaker, more otherworldly affair. As always with Green, it's a moot point as to whom this is addressed: the girl next door or the Big Guy upstairs.
Mark Pringle

63 The Velvet Underground: 'Pale Blue Eyes', from The Velvet Underground (MGM, 1969) 
Allegedly the straw that broke John Cale’s experimental back and drove him out of the Velvs, this saw Lou Reed returning to the gentle vein of early Velvets songs like ‘Sunday Morning’. But Cale was wrong if he thought Lou'd lost his bite: the songs on this album are as lyrically bleak as anything he’d written, and beneath the surface charm of this song is something darker. "‘Skip your life completely, stuff it in a cup’, she said. ‘Money is like us and time: it lies but can’t stand up/Down for you is up.’"
William Higham

62 Patsy Cline: 'I Fall To Pieces', single (Decca, 1961)
In which an inconsolable Patsy is advised by her ex-love to "act like we never kissed." But there is no escape: the very mention of his name cuts her like a knife. "You walk by, and I fall to pieces." Perhaps the Queen of Country Heartbreak's finest weepie.
Mark Pringle

61 Roy Orbison and k.d. lang: 'Crying', single (Virgin America, 1992)
"I was alright… for a while." Orbison topped even himself on a divine version of his 1961 classic that paired him with vocal disciple k.d. lang. "For you don't love me, and I'll always be… cry-y-y-y-y-y-y-ing…"
Melody Nelson

60 Michael McDonald: 'I Can Let Go Now', from Michael McDonald (1982)
"I was tossed high by love/I almost never came down…" The Doobies man solo and alone at the piano, singing a torchy, Sinatra-style ballad in that airy California-soul tenor. The perfect marriage of melancholy and vocal grace.
Ed Doheny

59 Everything But The Girl: 'Missing', single (Blanco y Negro, 1995)
"And I miss you/Like the deserts miss the rain…" The Todd Terry house mix of this plaintive gem only made it more piningly bittersweet. Tracey Thorn never sounded more direct or more dignified than she does on this exquisite song of loss.
Melody Nelson

58 Frank Sinatra: 'Where Do You Go?', from No One Cares (Capitol, 1959)
"What do you do when your heart's in pain?" The master of misery – of romantic desolation – is beyond all hope on this superbly bleak Alec Wilder/Arnold Sundgaard ballad.
Barney Hoskyns

57 Toto: 'I Won't Hold You Back', from Toto IV (Columbia, 1982)
Well, we had to get one '80s power ballad in there, didn't we? And '80s power ballads don't come much better than this, as Roger Sanchez's sampling of it for 'Another Chance' made only too clear. True, it wasn't inspired by the lissome Rosanna Arquette – unlike Toto's classic 'Rosanna' – but it's twice as pretty.
Ed Doheny

56 Dusty Springfield: 'I've Been Wrong Before', from Ev'rything's Coming Up Dusty (Philips, 1965)
"You held me tight, and everything seemed just right…" Pure class, pop perfection: over a chilling piano arpeggio, the velvet voice of blue-eyed soul weaves through Randy Newman's desolate lyric.
Melody Nelson

55 Brian Wilson: 'Caroline, No', single; also on the Beach Boys' Pet Sounds (both Capitol, 1966)
"It's so sad to watch a sweet thing die…" Brian at his most wistfully melancholic, especially when he ascends into falsetto for "you break my heart/I wanna go and cry…"
Ed Doheny

54 Hank Williams: 'I Can't Help It (If I'm Still In Love With You)', single (MGM, 1951)
"Somebody else stood by your side/And he looked so satisfied…" The jaunty, clip-clop rhythm notwithstanding, Hank makes every keening word here ring with pain – the sound of a smalltown joe who's been comprehensively crushed.
The Rev. Al Friston

53 Jimmy Donley: 'Think It Over', single (Chess, 1962)
"I prove my love, each day I live/My heart is yours, my soul I give…" The great lost voice of swamp pop pours out his heart to a faithless bayou maiden, pleading with her not to go… or at least to, uh, think it over.
The Rev. Al Friston

52 Two Tons O'Fun: 'Taking Away Your Space', single (Fantasy, 1980)
"Now I guess you're satisfied/When your friends told you that I cried… I cried! I cried! YES, I cried!!" If you thought the Two Tons were just about Weather Girls and raining men, check this lacerating widescreen masterpiece from the pen of Sylvester, which veers from disconsolate balladry to inflamed jazz-funk and back again, with the aid of a radical string arrangement and a bloodcurdling vocal from Martha Wash.
Cleothus Hardcastle

51 Elvis Costello: 'I Want You', from Blood and Chocolate (Imp, 1986)
"Did you call his name out, as he held you down?" Rarely has sexual jealousy been given such excruciatingly detailed treatment as EC gave it here – a slow, agonisingly intimate "love letter" that's stuffed with adoration and bilious reproach in about equal measures.
Nicky Parade

 50 Kris Kristofferson: 'Me & Bobby McGee', from Me & Bobby McGee (Columbia, 1971)
"It was somewhere near Salinas, Lord, I let her slip away/Looking for the home I hoped she'd find/But I'd trade all my tomorrows for a single yesterday/ Holding Bobby's body next to mine." If ever songwriting could punch a hole in your chest and squeeze your heart… and all this from a song that also contains the immortal line "Freedom's just another word for nothing left to lose"…
Simon Witter

49 Massive Attack: 'Unfinished Sympathy', single (Circa, 1991)
"How can there be a day without a night?" Just as Joy Division's 'Love Will Tear Us Apart' set its domestic misery to a proto-'80s dance beat, so Massive Attack frame Shara Nelson's gasping gospel anguish with a cluster of very busy percussion. 'Unfinished Sympathy' sounds like a disco mix of a southern soul – make that southwestern soul – ballad… yet somehow it all works.
Cleothus Hardcastle

48 Timi Yuro: 'Hurt', single (Liberty, 1961)
Italian-American soul from the rich contralto voice of La Yuro (left), who on this 1961 classic is – simply enough – "hurt". Singing sublimely over piano triplets, Timi wrings every last drop of grief from the lyric.
Barney Hoskyns

47 Alison Krauss: 'Dreaming My Dreams (With You)', from Forget About It (Rounder, 1999)
"Someday I'll get over you/I'll live to see it all through…" Marianne Faithfull's cod-country 1975 Irish hit gets a burnished pop-bluegrass makeover – all dobros and hair's-breadth close harmonising – with immaculate results.
Ed Doheny

46 Walter Jackson: 'Speak Her Name', single (Okeh, 1967)
A lush uptown-soul ballad from a Chicago baritone who sounded like the missing link between Jerry Butler and Scott Walker, 'Speak' combines grave dignity with haunted heartache, climaxing in the almost frantic "I don't want no one speaking her name!" Dig those congas in the coda too!
Cleothus Hardcastle

45 Tim Hardin: 'It'll Never Happen Again', from Tim Hardin 1 (Verve, 1966)
Like Robert Downey Jnr in Ally McBeal, arch-crooner Hardin stumbles so often you assume he’s gonna blow it, before delivering lines so touching they’d make any heart melt. The missing link between the drunken-bum beatnik of the ‘50s and the ‘70s New Man. "I remember our first affair/All the pain: always rain around my eyes/ It’ll never happen again."
William Higham

44 Dionne Warwick: 'Anyone Who Had A Heart', from Anyone Who Had A Heart (Scepter, 1964)
Lyricist Hal David is too often overlooked in the Bacharach and David partnership, but here he sparkles: "Anyone who ever loved/Could look at me and know that I love you/Anyone who ever dreamed/Could look at me and know I dream of you." And as ever, the pitch-perfect lost-little-girl Dionne makes the song her own: breathy, clipped and passionate in equal measure.
Sidney Falco

43 Chris Connor: 'Goodbye', from Sings Lullabies of Birdland (Bethlehem, 1954)
Made famous by Sinatra, this elegaic Gordon Jenkins ballad is actually rendered better by the playful, reflective Connor (right), who brilliantly suggests the pain she's feeling even as she's processing it in a refined, wittily civilised lyric. The final wistful "goodbye" – delivered as a sweet, breathy sigh – is chilling.
Art Sperl

42 Etta James: 'I'd Rather Go Blind', single (Cadet, 1967)
Coming on like a hellfire preacher, the Queen Mother of Soul updates that old religious image (‘If thine eye offend thee’, ‘An eye for an eye’) to great effect. "I, I’d rather go blind, boy, than to see you walk away with another girl."
Sidney Falco

41 Gillian Welch: 'One Morning', from Hell Among The Yearlings (Almo, 1998)
The sense of doom is right there in the gently duelling guitar'n'banjo intro. By the song's denouement, this mythopoeic tale of a mother who watches her son arrive home dead on horseback has chilled the listener to the bone. Deeply resonant in these times of war and loss.
Ed Doheny

40 David Ruffin 'Walk Away From Love', from Who I Am (Motown, 1975)
"It's not that I don't love you, you know how much I do/It's just a dread that shakes my body, that even I don't understand…" To the accompaniment of sweeping strings and a superslick Van McCoy "hustle" beat, the troubled ex-Temptation spins a harrowing tale of commitment-phobia.
Sidney Falco

39 The Byrds 'Here Without You', from Mr Tambourine Man (CBS, 1965)
Gene Clark's girl is away somehere, and boy does he miss her in this gentle blend of Beatles and Louvin Brothers. As usual, it's Clark's use of everyday imagery that's so disarming: "Streets that I walk on depress me/Ones that were happy when I was with you – It's so hard being here without you…"
William Higham

38 Ray Charles: 'Don't You Love Me Anymore', from Brother Ray Is At It Again (Crossover, 1980)
It's over, and he knows it: "Oh baby, somethin's wrong, won't you tell me?" Bewildered and angry, Brother Ray rails against the dying of love's light: "Forever didn't last too long; where, where did we go wrong?"
Mark Pringle

37 Gladys Knight & the Pips: 'Neither One Of Us (Wants to Be the First to Say Goodbye)', single (Tamla Motown, 1973)
"It's sad to think…we're not gonna make it." Motown's greatest chanteuse tears the heart out with this agonising can't-live-with/can't-live-without classic – not least when her voice cracks twice on the bridge. "There can be no way this can have a happy ending…" But there can be a final – and very tender – "goodbye".
Cleothus Hardcastle

36 Ben E. King: 'It's All Over', single (Atlantic, 1964)
An almost-forgotten, Bert Berns-produced uptown-soul masterpiece from the 'Stand By Me' man, this harrowing ballad cruises along on a bed of stately gospel organ and acoustic guitar before erupting in a sobbing, femme-backed chorus. "When I see two young lovers walking down the street/Oh how it kills me when I see their two lips meet…"
Barney Hoskyns

35 Todd Rundgren: 'The Last Ride', from Todd (Bearsville, 1974)
A cosmic blues-rock epic from the Philadelphian genius, featuring tempo changes, piledriver orchestration, bebop horn solo and some typically poignant little-boy-Todd lyrics: "It’s the last ride – our little game is over/It’s the last ride – it’s time to take you home/And we can’t cry, because we’ve seen it coming/No use running..."
William Higham

34 The Rolling Stones: 'Wild Horses', from Sticky Fingers (Rolling Stones, 1971)
"Graceless lady, you know who I am…" Probably playing in the background when a hundred hippie kids were conceived, this stoner favourite is raw and country-rootsy, and boasts one of Jagger’s most affecting vocals. Plus the production (by Jimmy Miller, with Glyn and Andy Johns) is so roomy it feels like it’s being played in the room with you.
Sidney Falco

33 Candi Staton: 'Young Hearts Run Free', single (Warner Brothers, 1976)
"You count up the years, and they will be filled with tears…" Staton's disco-inflected 1976 smash was the I-will-survive-era anthem of cheated-upon women: "Don't be no fool, when love really don't love you." But the sorrow bleeds through the quasi-feminist defiance and pumping 4/4 beat.
Cleothus Hardcastle

32 Spiritualized: 'Ladies and Gentlemen, We Are Floating In Space', from Ladies and Gentlemen, We Are Floating In Space (Dedicated, 1997)
"I will love you till I die/And I will love you all the time…" The opening track on Jason Pierce's sublime testament to amour fou-as-narcosis, 'Ladies and Gentlemen' hinges on the great arc of weeping guitar that rings out behind his numbed vocal – the cry of love itself.
Djuna Parnes

31 The Chi-Lites: 'The Coldest Days Of My Life', from A Lonely Man (MCA, 1972) 
This tear-stained epic begins with sound effects (cf the Temps' ‘I Wish It Would Rain’, the Intruders' ‘Walking In The Rain’ et al) then builds into an orchestrated piece mimicking those sounds. Like a man battling with the elements, singer Eugene Record battles against the sorrows of a broken heart: "They were the coldest days of my life, I had to run for cover/ Lord, take away the pain, don’t you know that it pours like rain…"
William Higham

30 Bob Dylan: 'Tangled Up In Blue', from Blood On The Tracks (CBS, 1975) 
"We drove that car as far as we could – abandoned it out West/Split up on the docks that night, both agreeing it was best/She turned around to look at me as I was walking away/and I heard her say over my shoulder, ‘We’ll meet again someday on the avenue’…" On Blood On The Tracks, Dylan found a way to combine the lyrical complexity of old ('Desolation Row', 'Gates Of Eden') with his more recent simple country-folk melodies ('Girl From The North Country', 'Down Along The Cove') to create his most perfect album. This is the album's outright highlight: a tale of love found, lost, found and lost again.
William Higham

29 Dolly Parton, 'Jolene', from Jolene (RCA, 1974) 
The national anthem of white-trash also-rans. Parton’s average-Jane begs local beauty Jolene not to take her man, acknowledging and flattering Jo’s looks before delivering the killer line: "Please don’t take him just because you can." It's great in the hands of the pneumatic Ms Parton; great too by obscure ‘70s funkster Kellee Patterson (no, really…) Oh, and the White Stripes don't do a bad version neither.
William Higham

28 James Carr: 'That's The Way Love Turned Out For Me', single (Goldwax, 1968)
Greater even than the great 'Dark End of the Street', this is the late James' crowning moment in the heartbreaker stakes – a feverish litany of indignities sung in a torn, perfervid baritone by a man who's extrapolated a kind of cosmic alienation from his hurt: "This old world keeps on turning without me/And that's the way love turned out for me…"
Barney Hoskyns

27 Roxy Music: 'Sunset', from Stranded (Island, 1973)
Despite throwaway camp theatrics like 'Editions Of You', Ferry was always at his best as a crooner: and this is one of his finest croons. Taken from Roxy's first album sans Eno – and their last consistent classic – 'Sunset' is a poignant observation accompanied, ironically, by their most Eno-esque arrangement ever: a stripped down pulse of piano, bass and treated-horns.
William Higham

26 Bettye Swann: 'Be Strong Enough To Hold On', single (Atlantic, 1976)
The ultimate country-soul ballad, sung by the ultimate country-soul siren – the nonpareil Bettye Swann, who here beseeches her wavering (married) lover not to give in to the manipulations of his spouse, who's just "using your little children/To try to get next to you…" Adultery never sounded so righteous.
Barney Hoskyns

25 The Shangri-Las: 'Past, Present and Future' (Red Bird, 1966)
"Was I ever in love? I called it love." Call me an old kitschmönger if you must: I happen to find this three-minute melodrama from the mind of George 'Shadow' Morton utterly sublime – and as tinglingly sad as any soul lamentation you could put up against it. Using Beethoven's 'Moonlight Sonata' as its musical base, Morton constructs a wonderful mini-symphony around the maudlin reflections of the great Mary Weiss. "This will never happen again," sings La Weiss. Quite.
The Rev. Al Friston

24 Little Anthony & the Imperials: 'Hurt So Bad', single (DCP, 1965)
"Like needles and pins, people say you've been making out okay/'She's in love, don't stand in her way'…" 'Going Out of My Head' may be the greater record – symphonically, anyways – but 'Hurt So Bad' simply can't be topped as an irruption of juvenile teen-pop agony.
Barney Hoskyns

23 Dennis Wilson: 'Thoughts Of You', from Pacific Ocean Blue (Epic, 1977) 
Finally getting the credit it deserves, drummer-Wilson’s marvellous solo album is a mostly-mournful look at his damaged West Coast life. On this song he sounds like Alex Chilton on ‘Downs’ as he rails against the very thing that gave him success, the Californian sun: "The sunshine blinded me this morning, love/Like the sunshine, love comes and goes again." Then with an unsettling choir build up over the middle eight – pre-empting Pink Floyd’s The Wall by a couple of years – he all but cries: "Look at love/ Look at love/ Look at love/ Look what we’ve done…" Harrowing stuff.
Sidney Falco

22 The Ink Spots: 'I Understand (Just How You Feel)', Trees Lounge original soundtrack album (MCA, 1996)
Over a sparse, jangly pub piano, Bill Kenny's ethereal tenor moan, oozing bittersweet yearning, booms his sympathy for the woman who has just broken his heart. "I understand/And darling you are not to blame/If when we kiss it's not the same/I understand it's not your fault, because your heart has changed its mind/You didn't mean to be unkind…"
Simon Witter

21 Erma Franklin: 'Piece Of My Heart', single (Shout, 1967)
"Didn't I make you feel like you were the only man?" Aretha's sis applies her grittier pipes to this fabulously masochistic classic, a Berns-Ragovoy pearl of a song made still more famous by ball-and-chain superstar Janis Joplin.
Cleothus Hardcastle

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.
William Higham

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…"
Barney Hoskyns

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.
Cleothus Hardcastle

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.
Barney Hoskyns

16 Billie Holiday: 'Don't Worry 'Bout Me' from Lady In Autumn (Verve 1959/1997)
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 desparation. Truly heart-rending late Lady Day.
Mark Pringle

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.
William Higham

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…"
William Higham

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.
Sidney Falco

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.
Ed Doheny

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.
Sidney Falco

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.
Ed Doheny

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.
Barney Hoskyns

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 heartache in them there grooves.
Sidney Falco

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.
Cleothus Hardcastle

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.
Djuna Parnes

5 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 fucking 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.
William Higham

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.
Ed Doheny

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 Much, who keeps going back, masochistically, to the woman who's destroyed him. One of Frank's all-time peaks.

Art Sperl

2 Roy Orbison: 'It's Over', single (Monument, 1964) BH
"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.
Barney Hoskyns

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.
Barney Hoskyns

PUBLICACIÓN:
Rock's Backpages, Winter 2001

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