Valentine's Day Special: 18 Heartbreak Songs

It’s less than a week before Valentine’s Day, which means love, chocolate, jewelry, and hearts. The hearts may be of the jewelry and chocolate variety when things are going well, but as these OGs (and now their kids) know, the hearts may also be broken. And no day of the year, made up or not, hurts more when your heart is broken than Valentine’s Day. So for everyone whose heart may be broken now, or who still bears the scars from the breaks of the part, OG Brian put together a phenomenal list of songs to be your soundtrack (and Brad couldn’t resist adding two more at the end). The list is so good that we decided just to post it on its own; the regular structure will be back shortly with a DC music special.

Hopefully the songs below ease the pain, or maybe just make it mean something different. Regardless of where they take you, we know that even when your heart aches the most, it is music that can heal. A different John Cusack character kicks off the list below, but all you need to do is ask Lloyd Dobler in Say Anything about music and broken hearts. And please post comments with your own suggestions.  

Album (um, songs) being rediscovered (at least 10 years old): “Nobody worries about kids listening to thousands, literally thousands of songs about heartbreak, rejection, pain, misery and loss.  Did I listen to pop music because I was miserable?  Or was I miserable because I listened to pop music?”  This quote comes from John Cusack’s lead character, Rob Gordon, in the movie High Fidelity (covered in my previous Needle Drop post) and accurately summarizes popular music’s long history of focusing on heartbreak as a theme, its appeal to young emotional people being fairly obvious.

Valentine’s Day is approaching, and your interest in it may vary (mine leans toward “made-up Hallmark holiday designed to boost profits for the greeting card, flower, and jewelry industries and if people love each other they don’t need an officially sanctioned day for it” but, hey, to each their own).  So we’re doing another list, sort of an anti-Valentine’s Day list of songs about heartbreak.  Full disclosure – I was inspired to lead with the above quote by a recent episode of the awesome podcast 60 Songs That Explain the ‘90s, but I came up with the idea for this over a month ago when I heard one of the songs below on the radio.  Really, I swear.

As is often the case, this list could be 10,000 songs long, but it’s just a selection, so it is almost guaranteed that someone’s favorite song or artist will not be included.  And as always, this is in no particular order, except for:

(1)    “Heaven Knows I’m Miserable Now” – The Smiths: I mean, it may be a cliché, but we had to start with the masters of mope, right?  For youth of a certain stripe of my generation, The Smiths were the soundtrack to teen depression.  The lyrics resemble a fellow Gen-Xer’s embarrassing 8^th grade diary (“In my life / Oh why do I give valuable time / To people who don’t care if I live or die?”), but it was perfect for the moment, is still a beautiful song, and one of The Smiths’ best, with Johnny Marr’s ringing guitars, Andy Rourke’s sparse but pulsing bass, and Mike Joyce’s propulsive drums contrasting starkly with Morrissey’s dour lyrics.  More full disclosure – given recent events in the news, I was tempted to lead with “Please, Please, Please Let Me Get What I Want” for SEO purposes, but I opted for the better song and chose to keep the incels from finding this blog because I’m a man of integrity.  Really, I swear.

(2)    “The Tears of a Clown” – Smokey Robinson & the Miracles:  Did anyone write or record better heartbreak songs than the folks at Motown?  Originally included on the 1967 album Make It Happen and co-written with Stevie Wonder, the song became a hit when it was re-released three years later.  It’s an upbeat number with clever lyrics about a man putting on a brave face after being dumped, that “it’s only to camouflage my sadness” and “cover this hurt with a show of gladness.”  I challenge you to find a pop song today that name-checks a legendary opera about a murderous cuckolded clown that was also referenced on an episode of Seinfeld.  I could have also gone with the wonderful “Tracks of My Tears” but this one gets the nod for spawning a bangin’ cover by The English Beat in 1979.

(3)    “Yesterday” – The Beatles:  OK, maybe Lennon and McCartney wrote better heartbreak songs than the Motown artists, but this is really a LeBron/MJ argument in that there’s no right answer (I’m kidding – MJ is better, and I won’t hear otherwise, and this is coming from a Knicks fan who’s still not over 1993).  “Why she had to go / I don’t know, she wouldn’t say / I said something wrong / Now I long for yesterday.”  Dammit, I’m not crying, you’re crying.  Speaking of which…

(4)    “Crying” – Roy Orbison:  I promise this list won’t just be old guys, but you gotta love a good transition.  And this song really has it all.  From the title to the opening beats to the acoustic guitar chords to the first lyrics (“I was alright for a while / I could smile for a while”) sung in Orbison’s rockabilly baritone, you know you’re in for an emotional punch.  But as the tone in his voice rises, so does the feeling, and he reaches the song’s summit by hitting those high notes while repeating the song’s title over and over.

(5)    “Back to Black” – Amy Winehouse:  Up until now, the songs have shown a certain response to heartbreak – misery, sadness, doubt, questioning.  In this massive hit, Winehouse covers similar themes but is more explicit and haunting in where these feelings take her.  The music itself is dark, and she sings of having to keep it together after a man leaves for a previous partner.  With the current knowledge, not just that she dealt with substance abuse but that she eventually died at age 27 of alcohol poisoning, the lyrics are a real kick in the teeth.  “We only said goodbye with words / I died a hundred times / You go back to her / And I go back to black.”

(6)    “Song Cry” – Jay-Z:  From 2001’s epic The Blueprint, Hova’s song laments an early breakup over his infidelity, and touches on themes of masculinity and emotion.  Because he’s “a man with pride,” Jay-Z raps “I can’t see ‘em comin’ down my eyes / So I gotta make the song cry.”  Still, he’s self-aware enough to understand that he is to blame (although, years later, Beyonce and her fans might disagree) when he shifts to “I know I seen ‘em coming down your eyes” and acknowledges that “I gotta live with the fact I did you wrong forever.”  Sounds like a love song, indeed.

(7)    “The First Cut is the Deepest” – Rod Stewart:  It’s easy to forget that Stewart wasn’t always treacly and sappy.  Way back when, he could be rocking, bluesy and soulful.  He was definitely the latter on this 1976 cover of a 1967 Cat Stevens song about a man who is still so stung by his first heartbreak that it’s hindering his ability to connect with the woman he is currently dating.  The song sets the tone with the opening lines, “I would have given you all of my heart / But there’s someone who’s torn it apart.”  Worth noting that the song is very representative of ‘60s and ‘70s relationship dynamics when Stewart (via Stevens) sings “I still want you by my side / Just to help me dry the tears that I’ve cried / And I’m sure gonna give you a try.”  Uh… thanks, Rod.  More full disclosure – this is the song that inspired me to write this list (really, I swear). This song that I had forgotten existed until I heard it over a month ago.  Not The Smiths, not Smokey, not The Beatles, not even the next artist on this list, but Rod fucking Stewart.  He deserves the credit or the blame.  Your choice.

(8)    “The Hula Hula Boys” – Warren Zevon:  Everyone drink!  Of course, I was going to include a Zevon song.  From 1982’s The Envoy, this song comes at an interesting time for Zevon.  After releasing three standout studio albums plus a live album from 1976-1980, he was in a creative rut and drinking heavily.  The Envoy was supposed to be his comeback album but, despite some solid-to-great songs, including this one, it wasn’t a success (he would eventually get his comeback with 1987’s Sentimental Hygiene).  And it’s not hard to see the parallels between his real life and the song’s POV character – a man vacationing in Hawaii with his wife or girlfriend, who ends up cheating on him repeatedly with the resort staff.  Except she’s not the villain.  He is self-pitying, neglectful, and presumably spending his days alone drinking himself silly.  “Yesterday she went to see the Polynesian band / But she came home with her hair all wet / And her clothes all filled with sand.”  He laments, “she’s gone with the hula hula boys / she don’t care about me” while claiming “I didn’t have to come to Maui to be treated like a jerk.”  No, she don’t care about you, and you were a jerk before you got on the plane.

(9)    “I Could Never Take the Place of Your Man” – Prince:  The heartbreak in the song doesn’t always belong to the singer.  One of Prince’s absolute bangers from 1987’s classic Sign O’ the Times, he sings of meeting a woman in a nightclub “with tears in her eyes” because “her old man ran away” and that he “left her with a baby and another one on the way.”  And she’s either looking for a new love, or a one-night stand, or a friend, or maybe she doesn’t even know what she wants.  So yeah, maybe there’s a little more here to unpack than just heartbreak.  But the song rocks in stark contrast to the sad lyrics.  There’s been some revisionist criticism of this song, asking who Prince is to tell this woman what she wants at this moment.  Maybe.  And maybe I’m not the right person to argue with this.  But it was the ‘80s, times were different, and the song kicks ass.  Lighten up, Francis.  More full disclosure – my wife is possibly the biggest Prince fan in the world, and I’m not including this here just to score brownie points.  Really, I swear.

(10) “September Gurls” – Big Star:  Here’s how you know I’m taking this list seriously.  I’ve saved one of my absolute, all-time favorite, desert island songs for #10.  I love this song so much, have listened so many times, have read so much about the band and their history and the recording of their albums, that I don’t know what else there is to say.  So I’ll just quote the brilliant Alex Chilton lines we all know: “I loved you / Well, never mind / I’ve been crying all the time / December boys got it bad.”

(11) “Ex-Factor” – Lauryn Hill:  A neo-soul classic off Hill’s 1998 masterpiece The Miseducation of Lauryn Hill.  Hill belts out pure emotion over mid-tempo beats, singing about a cyclical, toxic relationship that neither she, nor her partner, can quit (“Loving you is like a battle / And we both end up with scars”).  The heartbreak is mostly for the partner that she loves, even though they are bad for each other, but you can also hear a hint of heartbreak for herself.  Not self-blame, but questioning why she isn’t strong enough to cut this person loose (“How can I explain myself? / As painful as this thing has been / I just can’t be with no one else”).  A brutal examination of a failing relationship and a brutal examination of one’s self.

(12) “Always on my Mind” – Willie Nelson: If the subject is heartbreak, I needed to include at least one country song, so I might as well go with one of the greatest songs ever about regret.  Originally recorded in 1972 separately by Gwen McCrae and Brenda Lee, Nelson covered the song 10 years later and scored a top five hit and number one country hit.  While there have been many versions, including those by Elvis Presley and the Pet Shop Boys, Nelson’s is definitive.  You hear the sorrow in his voice as he sings, “Maybe I didn’t love you / Quite as often as I should have / Maybe I didn’t treat you / Quite as good as I should have.”  Even though he’s hopeful “that your sweet love hasn’t died” and is looking for “one more chance to keep you satisfied,” odds are he knows it ain’t happening.

(13) “Don’t Look Back in Anger” – Oasis:  Of the songs on this list, this is the one I debated including the most.  Who really knows what this song is about?  I don’t think Noel Gallagher even knows what this song is about.  It can be understood as a reflection on a bad experience with a woman named Sally.  Or it can be a bunch of nonsense and dropping in the name Sally sounded cool.  I’d believe either.  But the song is amazing and when the Gallagher brothers eventually decide to reunite, the crowd at Wembley will scream along to the chorus.

(14) “The Gift” – The Velvet Underground:  OK, now I’m just messing with you.  I love the Velvets, but this song is batshit crazy.  Eight minutes of a John Cale spoken word story over guitar/bass/drums about a paranoid, lovesick long-distance boyfriend who mails himself to the girl and ends up getting stabbed in the head when she opens the box.  Less about heartbreak, and more about psychotic obsession.  Probably David Lynch’s favorite song.

(15) “A Case of You” – Joni Mitchell:  Finishing out this list with two iconic songs, the first of which is from Mitchell’s landmark 1971 album Blue.  A perfectly beautiful song about a relationship that has run its course, with Mitchell conveying both regret and acceptance.  The song’s entire thesis is neatly summarized in its opening lines – “Just before our love got lost you said / ‘I am as constant as a northern star’ / And I said, ‘Constantly in the darkness / Where’s that at? / If you want me I’ll be at the bar.’”  It’s all there at the beginning, but thankfully it keeps going.

(16) “If You See Her, Say Hello” – Bob Dylan:  This has been such a frequent topic for him, I could have written an entire list of just Dylan songs (think of legendary tracks like “Don’t Think Twice It’s Alright,” “Girl from the North Country,” “Tangled Up in Blue,” and “It Ain’t Me, Babe” for starters).  From 1975’s masterful Blood on the Tracks, this song is typical cryptic Dylan – either it’s a fictional story about being rejected by a woman, an autobiographical tale about the same, or maybe a mix of both.  He’s never been fully open about it.  Despite minimal percussion and sparse instrumentation, the music is full and Dylan’s voice is sharp.  And the lyrics range from the regret of heartbreak (“We had a falling out / Like lovers often will / And to think of how she left that night / It still brings me a chill”) to the denial and anger that heartbreak can become (“Oh whatever makes her happy / I won’t stand in the way / Though the bitter taste still lingers on / From the night I tried to make her stay”). (Brian)

Bonus Heartbreak (Brad):

(17) “Here’s Looking at You, Kid” – Gaslight Anthem: This is really 3 heartbreak songs in one from The ‘59 Sound, one of the great albums ever about the dreams and travails of heartbroken youth. On this track (which should have been the album closer), Brian Fallon is talking to someone – his oldest friend? a new partner? another part of himself? – about three different women (Gail, Jane, and Anna) who broke his heart at various points before he became a rock star when, presumably, he now has all the girls he could desire (or does he?). He sings not only about his experience with them but imagines what their relationships would have become, meaning he’s regretting both what he had and what he never got to have. It’s always struck me that the song is about 3 women, when nearly every other heartbreak song is about one relationship that ends, because it adds that layer of perspective, of understanding why she left, but of realizing that the pain never really goes away. Instead, we learn that the pain just gets built on top of, like the discoveries archeologists make in places where three or four societies have come and gone in one place. The part that brings all 3 together -- “But boys will be boys and girls have those eyes/That’ll cut you to ribbons sometimes/And all you can do is just wait by the moon/And bleed if that’s what she says you ought to do” – is as perfect a verse as you can get about the things love can make you do, and feel.

(18) “Dry Your Eyes” – The Streets: Although Brian has put together an incredible list, I will go to my grave saying this is the most heartbreaking song of all time. Not because it is as poetic as The Smiths or The Beatles, although it contains remarkable lyricism, but because it’s physical. That is, it’s more of a play than a song, a blow by blow account of the moment your world collapses, and at its core, it’s a song about the actions, the way the bodies move and react, as much as the heart and the emotions. Or rather, how the body moves in relation to the heart. The song comes from a remarkable concept record called “A Grand Don’t Come for Free” that tracks The Streets (the stage name of MC and musician Mike Skinner) through a crazy series of circumstances, mostly about his looking for a thousand pounds that has gone missing (stolen? misplaced?), but the relationship with Simone is always the most captivating piece for me. We’re along for the ride from the moment they meet in a bar through the highs and lows and to the end, and at least I’m always rooting for them to make it. But when it crashes, the song focuses on their hands, their bodies, their actions. First there’s the moment Mike understands what’s happening: “So then I move my hand up from down by my side/Shaking, my life is crashing before my eyes/I turn the palm of my hand up to face the skies/Touch the bottom of her chin and let out a sigh.” And after back and forth, appeals, prayers, protests, finally, she’s finished: “She pulls away my arms that tightly clamp around her waist/Gently pushes me back as she looks at me straight/Turns around so she's now got her back to my face/Takes one step forward, looks back, and then walks away.” What’s more heartbreaking than the girl of your dreams taking one last look back at you and walking away forever? Nothing. As Brian would say “Really, I swear.”