Lucky 13: A Baker’s Dozen of Favorite Songs That Will Break Your Poor Little Heart

Back in November, I devoted a blog to 13 of my favorite love songs. As these things go, that blog got a lot of attention, at least on a couple of my social media accounts. Many people pitched in with their own recommendations, and took me to task for some of the songs I left out. Many of the songs they thought I should include didn’t really fall into the category of “love” songs, but “love gone wrong” songs.

So today’s blog is devoted to songs about heartbreak, which may or may not be the most popular musical theme (maybe God holds the top spot, I don’t know).

A quick word of explanation:

  • Not all of these songs are about heartbreak, per se. A couple are more rooted in anger than sadness. Specifically, anger that some clueless goof could possibly end a relationship – before the singer could end it first!
  • This list reflects my age and geography. All but three were recorded before 1987, which is a reflection of my advancing years. All were recorded by artists in English-speaking countries: the U.S., the UK, Ireland and Australia. I’m sure there are thousands of modern, non-English songs that deserve recognition. But I am who I’m is.
  • YouTube links to the songs are included in all of the artist names.

The songs are in no particular order. As always, the list is fluid, and a month from now I might have a completely different one.

Anyway, on to the tear jerkers….

I Can’t Help It If I’m Still In Love With You, Hank Williams: No genre does heartbreak as well or as often as country music, and no singer or songwriter did it as well or as often as Hank Williams. The man’s whole life was a master class in heartbreak: older than his years, sadder than a dying star, beset by a lifetime of back pain he tried to ease with booze and drugs, dead before he turned 30, on New Year’s Day. You could fill this whole list with Hank songs, but I always thought this one had the perfect combination of melancholy music and gut-wrenching lyrics (It’s hard to know another’s lips will kiss you). A whole bunch of cover versions are out there, including a nice one by Linda Ronstadt with backing vocals by Emmylou Harris. But Hank’s is still the standard. Note: This, of course, is Hank Williams Sr., not Junior, who can’t hold a candle to his pop in any way, shape or form, musically or otherwise.

Tangled Up In Blue, Bob Dylan: It was either this or the gentler “Buckets of Rain,” both from Dylan’s monumental breakup album, Blood on the Tracks. The album was written and recorded while Dylan was parting ways with his wife Sara. I settled on “Tangled” because it’s an epic tale of love gone wrong, and one of the truly great singles ever. Plus, it ends with what might be the saddest and most accurate reason so many close relationships flicker out:

We always did feel the same
We just saw it from a different point of view

Diamonds and Rust, Joan Baez: While we’re on the subject of Dylan….this is Joan’s take on her complicated relationship with Bobby. They were lovers for a while (I guess), but they were mostly kindred souls who served as a kind of Adam and Eve of the early ‘60s folk music revival. The melody on “Diamonds and Rust” can best be described as haunting, played in F minor and accompanied by a steel guitar (I think), some kind of synthesizer (I think), and various other instruments wafting in the background. The lyrics are beautiful and poignant: Speaking strictly for me, we both could have died then and there….

Back to Black, Amy Winehouse: Amy cuts right to the chase in the song’s first two lines: He left no time for regret/Kept his dick wet. Well, that pretty much gets to the heart of the matter, doesn’t it? The singer has been hooking up with a guy, and the guy wants to go back to whoever he was hooking up with before, leaving the singer out in the cold. Winehouse’s lyrics are appropriately dark – We only said goodbye with words/I died a hundred times – and her voice is a cocktail of acidity and bottomless sorrow. But what really grabs me is the music, which has a certain dirge-like quality. Some music writers liken “Back to Black” to 60’s girl group pop because of the bouncy piano. I can see that, but I still hear more of a torchy jazz ballad here, a better fit for Billie Holiday than the Shirelles. And like Billie, Amy died too young after years of substance abuse.

Whipping Post, The Allman Brothers Band: She took all his money, wrecked his new car; now she’s with one of his good-time buddies, just drinkin’ in some crosstown bar. Any questions? Plus: one of the great bass lines of all time, courtesy of Berry Oakley, who died in a motorcycle crash a little more than a year after guitarist Duane Allman also died in a motorcycle crash.

All of Me, Dinah Washington: No, this isn’t the song by John Legend. It’s an old jazz standard recorded by many. The singer wonders why her mean old man doesn’t just take every part of her – her lips, her arms, her eyes – since he went and took her heart. The version I really dig is a live take Dinah did at the Newport Jazz Festival in 1958. You really should hit the link. The video is amazingly high quality for the time, in color, and takes you right into a moment in time that is as dead as the dinosaurs, but still looks like it could have happened yesterday. I just love the melody and arrangement here. Dinah’s bluesy voice is the star, but it’s also cool seeing her take a turn on the vibes. Bonus points: Our oldest daughter has learned this song on piano, and it’s perfect. Absolutely perfect.

Fairytale of New York, The Pogues: It was Christmas Eve, babe, in the drunk tank…..If I ever write a blog about the 13 funniest songs ever, this will make that list as well. It’s the greatest song ever about the bitter back and forth between two disgruntled lovers. Lyrics like You were handsome/you were pretty quickly devolve into You’re a bum, you’re a punk/you’re an old slut on junk. Brilliant. Few singers do a better job of capturing that particularly Irish sense of doom and melancholy than Shane McGowan. His duet partner here, Kirsty MacColl, more than holds her own as the narrator’s long-suffering better half. I particularly like the female singer’s response to her male counterpart in this exchange:

Him: I could have been someone
Her: Well so could anyone

Note: In a sad postscript, MacColl died tragically and heroically in 2000 at the age of 41. She and her teenage sons were diving at the Chankanaab reef, part of the National Marine Park of Cozumel, Mexico. It was a designated diving area that watercraft weren’t supposed to enter, but a powerboat came plowing in at high speed. MacColl noticed that one of her sons was in the boat’s path. She swam over and pushed him out of the way. He survived with minor head and rib injuries, but she was struck by the boat’s propellor and died instantly of severe chest injuries.

My Favorite Lies, George Jones: Here’s a singer whose catalog has enough heartbreak in it to make the world weep well into the next century. Many George fans are probably saying, How can you not have “He Stopped Loving Her Today” on here? Fair point. But something about “My Favorite Lies” always hits me in the old ticker. Maybe it’s the way the singer tries to deny his own pain. Probably it’s the way George’s voice cracks when he croons, I’ve completely forgotten…how-ow-ow to cryyyyyy….That ‘un gets me every time.

Torn, Natalie Imbruglia: A piece of pretty ‘90s Aussie pop with a catchy hook that sticks in your ear long after the final note fades away. Imbruglia’s version might have sold a zillion copies around the world, but it wasn’t the original. That honor goes to the L.A. alternative band Ednaswap, whose version is much harder. The refrain tells you all you need to know about the message within:

I’m all out of faith, this is how I feel
I’m cold and I am shamed
Lying naked on the floor
Illusion never changed
Into something real

Go Your Own Way, Fleetwood Mac: Like Dylan’s Blood on the Tracks, Fleetwood Mac’s Rumours is another epic breakup album that was famously recorded when four-fifths of the band were splitting up with each other. Lindsay Buckingham wrote “Go Your Own Way” to document his split with band mate Stevie Nicks, who wrote “Dreams” to document her split with Buckingham. Both songs became massive hits. I just like the sheer, unrelenting sonic force of “Go Your Own Way.” Plus it has a catchy melody. And a couple of vicious lines. Note: The other couple involved in a breakup, Christine and John McVie, kept things much more civilized and close to the vest, in proper Brit fashion. Buckingham and Nicks, being American, let the switchblades come out.

This Masquerade, George Benson: I’ll always contend that the 1970s was the best decade for soul music, and nothing else comes close. You could choose from an endless list of soul/R&B songs detailing love gone wrong, from artists like Al Green, Gladys Knight, Marvin Gaye, the Stylistics, the Manhattans, the Chi-Lites, Harold Melvin & the Blue Notes, the Temptations, the Delfonics, Bill Withers, the Three Degrees, Billy Paul, etc. Guitarist George Benson fit more comfortably into the jazz category, or more precisely the jazz/fusion category. But he brings out the soul in this rendition of a Leon Russell song. “This Masquerade” appears on the landmark 1976 fusion album “Breezin’” and is the only non-instrumental on it. The production is slick and crafted to a fine edge, but George’s guitar playing, vocals and scatting give it a raw, bluesy feel.

96 Tears, Question Mark & the Mysterians: This song is similar to “Go Your Own Way” in that it uses sonic force to highlight a breakup’s anger rather than heartbreak. The singer is out for revenge. He’s gonna make his estranged lover cry cry cry 96 tears. He’s gonna be on top, and his lover is gonna be way down there, looking up. The allure for me is the Vox Continental organ from Frank Rodriguez, which is so nasty it’s practically taunting the listener. “96 Tears” is a classic of mid-60s garage rock that reached the top of the charts in 1966, played by a band of Mexican-Americans from Michigan.

Can’t You See, The Marshall Tucker Band: I got my first stereo on my 15th birthday. It was a cheap Panasonic model with a couple of small speakers and a combination receiver/amplifier. Three of the first albums I remember buying were the Doobie Brothers’ The Captain and Me, Grand Funk Railroad’s We’re An American Band, and Marshall Tucker’s The Marshall Tucker Band. I wore out the grooves on the MTB album, and “Can’t You See” was my favorite track. It’s still my favorite Marshall Tucker song, thanks to lead guitarist Toy Caldwell’s growling vocals and bluesy riffs.

Note: The Marshall Tucker Band were from Spartanburg, S.C., just a short hop down I-85 from my home in Charlotte. Their bus driver lived in Charlotte, one neighborhood over from mine. The first time my friends and I saw the tour bus parked on the street we basically freaked out. We ended up knocking on the front door of the house and I told the guy who answered, “I’m freaking out!” He said, “Well don’t freak out!” His name was Buddy Carpenter, and he couldn’t have been nicer. Somewhere there’s a picture of me in front of the bus, circa 1975. So maybe the song’s inclusion on this list is rooted in nostalgia. You got a problem widdat?

Final note: I don’t know if there’s any cosmic connection involved, but it occurs to me that quite a few of the musicians and singers listed above died well before their time. It probably just comes down to the nature of artists and musicians. Those who died before the age of 50 include the following: Hank Williams; Amy Winehouse; Duane Allman and Berry Oakley (Allman Bros.); Dinah Washington; Kirsty MacColl (the Pogues); Toy Caldwell and Tommy Caldwell (MTB).

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