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Rock's Backpages 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. So get your handkerchiefs ready... here come the next twenty, from Michael McDonald to Gillian Welch. -- Barney Hoskyns, Rock's Backpages


60 Michael McDonald--"I Can Let Go Now," from Michael McDonald (1982): "I was tossed high by love/I almost never came down..." The Doobie Brothers' 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.

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.

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.

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.

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.

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..."

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.

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.

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.

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.

50 Kris Kristofferson--"Me & Bobby McGee," from Me & Bobby McGee (Columbia, 1971): "It was somewhere near Salinas, Lord, I let her slip away..." 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"...

49 Massive Attack--"Unfinished Sympathy," from Blue Lines (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.

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

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.

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!

45 Tim Hardin--"It'll Never Happen Again," from Tim Hardin 1 (Verve, 1966): Like Robert Downey Jr. 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."

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..." And as ever, the pitch-perfect lost-little-girl Dionne makes the song her own: breathy, clipped and passionate in equal measure.

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, 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.

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."

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.

Pt 4: Nos. 40-21 coming soon!!

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