“By the Time I Get To Phoenix”: performed by Glen Campbell (1967); written by Jimmy Webb. Called the "greatest torch song ever written," by Frank Sinatra, "By the Time I Get To Phoenix" is unique among breakup songs in its lyrical structure. The song chronicles a man's travels as he runs away from a woman, and speculates on her state of mind as he hits each stop on his flight from her. She goes from smiling because she knows he's coming back, once again, to the sad realization he's not coming home this time.
Campbell was driving one day and, after hearing the Johnny Rivers version of the song, told himself he could make it into a hit. That he did, as it became the third-most performed song from 1940 to 1990. There was an inexplicable fit between Campbell's expressive voice and Webb's poignant, lamenting lyrics—one that can also be found in “Galveston” and “Gentle On My Mind.”
“I Would Rather Go Blind”: written by Ellington Jordan, with co-writing credits to Billy Foster and Etta James; performed by Etta James (1967). “I would rather go blind boy than to see you walk away from me.” There's no ambiguity about that sentiment, and Etta James uses her fiery, earthy contralto to its full effect in expressing it. Any guy hearing her sing this two-chord heart wrencher to him would feel like he's the only man on earth. The lyrics convey, with such economy and foreboding, that first dreaded inkling that one's lover is leaving: “Something deep down in my soul said cry, girl/When I saw you and that girl walking around.”
“Cry Me A River”: written by Arthur Hamilton (1953); performed by Julie London (1955). This must be the most haunting “revenge breakup song” ever performed. There's no pining for lost love, no tears; instead, cold-blooded retribution. Plenty of women take their man back after he's left them, only to crawl back teary-eyed and contrite. But the narrator of this song is over this lout, and she's having none of his whining. Smoky-voiced Julie London sings, “And now you say you love me/Just to prove you do/You can cry me a river/Cry me a river/I cried a river over you.” She’s immune to her ex’s pain, given all the heartache the callous hound’s given her.
“In The Wee Small Hours Of The Morning”: written by David Mann and Bob Hilliard; performed by Frank Sinatra (1955). Sinatra did upbeat albums about romance in full bloom, as in Songs For Swingin’ Lovers, but when he wanted to explore the darker side of love, he was sure-handed. This song, from the album Wee Small Hours, which has been called the first “concept album,” has a calming sound. It could be sung to a baby as a lullaby, as babies can't understand the sadness of the words. But the sadness isn't the histrionic sort that makes the narrator sound on the verge of a breakdown. It's a sadness that's been weathered through at its most acute point, and now lingers on as insomnia-inducing melancholy that comes and goes.
It's a mournful song about losing sleep over lost love, yet there's a grain of hope—hope which could be delusional: “When your lonely heart has learned its lesson/You'd be hers if only she would call/In the wee small hours of the morning/That's the time you miss her most of all.” So many musicians have done versions of this song—including Sting, whose hubris must've gotten the better of him—but Sinatra owns it. Who this song’s aimed at, a matter of breathless speculation, is irrelevant. It's the singer’s job to transform personal experience into universal feelings, and nobody has ever done that better than Sinatra. Not only did the singer have an otherworldly command over lyrics and vocals, but he packed about 50 times the average amount of experiences into one lifetime. That produced a vast pool of emotional resources to draw upon whenever he stepped up to the microphone, manifested by restraint when necessary, subtle adjustments in phrasing to suggest mood changes, elongation of syllables, and volume modulation at just the right time.
“Cold Cold Heart”: written and performed by Hank Williams (1951). Breakups are about sadness, and the Alabama-born troubadour knew how to do sadness. Hank Williams, who once told a live audience that this song had made him more cash than any of his songs, led a hard, tumultuous life with plenty of women problems. So when he sang from the heart, which was always, he connected. “Cold Cold Heart” presents a new angle on the breakup song in that it’s about how a previous lover of the woman he pines for now has messed with her heart so badly that she can't love anymore: “Another love before my time/Made your heart sad and blue/And so my heart is paying now/For things I didn't do.”
“Cold Colds Heart” could be called a “prelude to a breakup” song, as the couple doesn't appear to be officially split up yet: “The more I learn to care for you/The more we drift apart/Why can't I free your doubtful mind/And melt your cold, cold heart?”
“Tangled Up in Blue”: written and performed by Bob Dylan (1975). “This is a song,” said Bob Dylan, “that took me ten years to live and two years to write.” That is to say, “Tangled Up In Blue,” with its seven verses, is about as far as it gets from one of those back-of-the-envelope songs that musicians talk about writing in 15 minutes on a tour bus. It's also a song to show to all the naysayers about Dylan's singing ability, because he sings the hell out of this one. At its core, it's a breakup song, but neither one that fits the common mold, nor one that's easy to nail down. It appears to be about a love affair that, while it ended by mutual consent, the narrator’s on a journey to recover: “She turned around to look at me as I was walking away/I heard her say looking over her shoulder, we'll meet again some day/On the avenue/Tangled up in blue.” “Tangled up in blue” is one of the more memorable phrases in musical history. But what does it mean? Nobody knows but it could be interpreted as a man afflicted with the romantic blues who’s gone on the road in an attempt to “untangle” himself. The memory of the woman he split with years ago is always on his mind as the song takes the listener on a meander through time and culture. “But all while/While I was alone/The past was close behind/I see a lot of women/But she never left my mind, and I just grew/Tangled up in blue.”
“Crying”: written by Roy Orbison and Joe Melson; performed by Roy Orbison (1961). This one's a weeper with the potential to fall into a maudlin pit if not for Orbison’s stunning, operatic vocal delivery, which he uses to elongate “crying” into five syllables to emphasize his pain. Orbison didn't compose his songs in the conventional manner of verse, verse, chorus, etc. He started them with a slow burn that built itself into a thundering crescendo that showcased a vocal power that reliably delivered a grandiose emotional wallop. Orbison moves into goosebump territory as his voice soars up in register with his conclusion to “Crying”: “Crying over you/Crying over you/Yes, now you're gone/And from this moment on/I'll be crying crying, crying, crying/Crying, crying, over you.” It's perhaps the most soaring, dramatic song ending in pop music history.
“Heard It Through the Grapevine”: written by Norman Whitfield and Barrett Strong (1966); =performed by Marvin Gaye (1968). This song jumped off the radio the first time I heard it. It went to the top of the Billboard Pop Singles chart for seven weeks from December 1968 to January 1969, overtaking the Gladys Knight & the Pips version of the song to become Motown’s biggest hit up to that point. The breakup “twist” here is that the singer hears about his lover’s infidelity via the scuttlebutt: “Ooh ooh, I bet you wonder how I knew/’Bout your plans to make me blue/With some other guy you knew before.”
Several things stand out in this song. On the subtler side, there's Motown session legend James Jamerson’s bass line, and then there's Gaye’s fierce vocals, befitting of the desperation of a man who sings, “I'm just about to lose my mind.” There's a feeling of paranoid dread hanging over this song. It begins with the ominous drumbeat in the intro, and then the organ and guitar up the anxiety level before the horns signal the wounded anxiety of the words to come—an anxiety accentuated by Gaye singing above his natural range. Straining to hit those high notes, he sounds on the verge of a breakdown.
“Heard It Through The Grapevine” is no ordinary pop song. Motown chief Barry Gordy didn't want Gaye to record the song because it worked against the smooth image he was trying to create for his musical goldmine. He was wise to relent, as it's one of the greatest songs his record label ever produced.
“Back To Black”: written by Amy Winehouse and Mark Ronson; performed by Amy Winehouse (2006). Winehouse’s boyfriend left her for another woman (an alternative theory is that it was cocaine instead of a lover), and the result is this resigned, world-weary song, with its “back to black” metaphor referring to the depression and alcohol abuse that would eventually kill her: "And I tread a troubled track, My odds are stacked/I'll go back to black."
“Back To Black” has the girl-group sound of the 1950s and 60s that informs much of her music, and the arrangement and production reference the “wall of sound” technique Phil Spector employed with such remarkable results in his work with The Ronettes—in particular, “Be My Baby.” There's a bass, drums, two guitars, piano, percussion, a four-piece horn section, a 16-piece string section, all soaked in reverb. It's a multi-layered background with a power that's enhanced by Winehouse’s delaying her phrasing behind the beat to create an irresistible, swinging groove.
“Hey, That's No Way To Say Goodbye”: written and performed by Leonard Cohen (1967). Cohen’s sparse, minimalistic songs, with their elegant lyrics delivered in his monotonic voice have proven to be of great solace to many suffering from despair, and this one’s no exception. The tone of the song is that of a man who's no stranger to breakups. He's realistic about love affairs and knows not all are destined to last. He's found a way that, in his mind, “works” for him when the inevitable moment comes to say goodbye, but it doesn't happen that way for him in real life. Cohen sings of the nice moments they shared, but then sings, “But now it's come to distances and both of us must try.” And then, “Your eyes are soft with sorrow/And that's no way to say goodbye.” He wants the split to be a pragmatic agreement that they're not compatible, but her tears (and maybe his) conflict with his wishes. The lyric, “Hey, that's no way to say goodbye,” is Cohen's wry commentary on how things don't always go the way they “should” go when the breakup moment comes.
