The 10 Saddest Songs Ever Written

When I say "saddest" pop song I do not mean the most depressing, for there are a lot of sulky songs  out there; "'Cause I'm dying inside and nobody knows it but me..." Nor does this list consist of the most nihilistic songs, of which "Death Metal" and "Grunge" have kindly obliged; "The world is a vampire, sent to drain..." Thank you for that master stroke of wisdom, Mellon Collie and the Infinite Corgan. For some such a list may seem depressing, and indeed it is in some ways- but the aim of this post has not been to point out depressing things (which is easy enough). Rather it is to highlight certain songs that, poetically speaking, capture some of life's most tragic moments- which are beautiful even if they are sad. In any case, wherever one can still sing their pain, hope remains. Just ask that Maroon 5 dude who sings the words "I am in misery" as if he were the happiest man alive.                    

10. I Can't Make You Love Me - Bonnie Raitt

A beautifully written song, this ballad, cowritten and performed by the blues artist Bonnie Raitt, is in many ways self explanatory. The verse details the story of a woman who is trying to come to terms with the fact that her partner (presumably) does not share the same affection for her that she has for him. In the process, she compromises herself by virtue of the fact that she still wants to be with him physically; "Lay down with me, tell me no lies, just hold me close, don't patronize... I'll close my eyes, then I won't see the love you don't have when you're holding me. Morning will come, then I'll do what's right, just give me 'till then to give up this fight... and I will give up this fight..." But what makes this song so unbearably sad is that universally relatable human experience wherein we love someone (or at least believe that we do) and we realize that this person feels nothing for us in return. Indeed, perhaps they even wish that they did feel the same, but the the truth is that one just can't manufacture those type of feelings- no matter how hard they try; "'Cause I can't make you love me if you don't. You can't make your heart feel something it won't. Here in the dark, in these final hours, I will lay down my heart, and I'll feel the power, but you won't." So there you are on the outside looking in, pouring your heart out to a person who looks back at you with eyes as disinterested as a stranger's. If you are interested in another beautifully tragic song performed by Raitt, I highly recommend the song "Angel of Montgomery".


9. The Boys of Summer - Don Henley

If the Cars' "Magic" is the epitome of a happy summer song, then this song by former Eagles drummer Don Henley is its ultimate antidote. It expresses everything that we hate about the summer, namely the feeling we had in our youth when it was coming to an end; "Nobody on the road. Nobody on the beach. I feel it in the air, the summer's out of reach. Empty lake, empty street, the sun goes down alone. I'm driving by your house, though I know you're not home." If summer is all about the atmosphere and the people, then this image reveals that sinking feeling we get when all of the drama and romance once again goes back into hiding. But this song is more than just some seasonal instruction guide, it is about the doubt, sorrow, and ambivalence one experiences as they leave their childhood and come face to face with the reality that those people and places are no longer really there in the way they were; "I'm driving by your house, though I know that you're not home." Perhaps she hasn't been at "home" in that house in quite a long time. However, the chorus reveals a last attempt to recapture those days of old; "I can see you, your brown skin shining in the sun, you got your hair combed back and your sunglasses on, baby. I can tell you my love for you will still be strong, after the boys of summer have gone." It is as if he is still fighting some old battle in his head between his love interest and those "boys" that seem to have a different agenda for the summer. At any rate, the video lends itself to such an atmosphere, for it is shot in black and white, and features the central figure at different stages in his life. This seems to be an attempt to play up the nostalgia angle. The last verse is the most tragic of all, perhaps because it expresses the very essence of why the message is so sad; "Out on the road today I saw a Dead Head sticker on a Cadillac, a little voice inside my head said don't look back, you should never look back." In the video, when he utters this line, the central character- at every stage in his life- turns around a looks behind him. And with a look of tired resignation, the last image you see is of Henley looking forward again into the grey autumn streets.


8. Angel of the Morning - Juice Newton

Originally written in the 1960s by Chip Taylor, the version I grew up with is the one by Juice Newton. It seems to detail the story of a young woman who is so enamored with an older man that she is willing to give away the whole farm for (along with the milk) in return for nothing; "There'll be no strings to bind your hands, not if my love can't bind your heart. And there's no need to take a stand, for it was I who chose to start. I see no need to take me home. I'm old enough to face the dawn." There's a lot to say here, but I suppose the line that reveals the most is the girl's hope that she can "bind his heart" through physical intimacy. How often does it happen that a young girl thinks that she can keep a man if she will only sell out physically to him? Far too often to mention. Such behavior, more often than not, actually provokes the opposite reaction in a man (fair or not). But what's even more tragic is the fact that this woman seems more than a little prepared to get used. In fact, she has practically resigned herself to this terrible fact; "Just call me angel of the morning, angel. Just touch my cheek before you leave me." 'Blessed is he (or she) that expecteth nothing, for he shall not be disappointed!' I suppose what makes the lyrics so poignant, however, are the startling descriptions of the awkward and pitiful circumstances that surround the one that has made this devil's deal; "Maybe the sun's light will be dim and it won't matter anyhow. If morning's echo says we've sinned, well it was what I wanted now. And if we're victims of the night, I won't be blinded by the light." One can almost feel the sting of the morning sunlight, making its way into the room, as this guy avoids any eye contact with the girl, only to shuffle away to the land of "anywhere but here".


7. Diary - Bread

This song is like a lesson in why one should never read the diary of another, or eavesdrop on a conversation that is about you but is not meant for you. The benefit of the knowledge gained is not equal to the amount of anxiety and sorrow that usually accompanies it. We hear enough negative things out there. The last thing we need to do is to go around scouting for bad (or even good) things. Besides all that, we may not even understand the entire nature of the conversation we overhear. In any case, this is an example of how reading something that is not your business, delivers more sorrow than good. One of the reasons it is particularly tragic is because the words that this girl wrote in her diary were extremely positive. As a matter of fact, much to his surprise, the object of his affection, who seemed previously indifferent to him, now has seemingly expressed her profound affection for him. And so in the first chorus he talks about all the things that he will give to her; "And as I go through my life, I will give to her, my wife, all the sweet things I can find". But as he confronts her about these feelings, she behaves in her usual cold and indifferent way- at which point he realizes, much to his embarrassment, the love that she expressed in the diary was for someone else. It is tragic enough not to be loved by someone whom you love (as was the case with Bonnie Raitt), but it is even worse to have laid your heart on the line thinking that that person has the same affinity for you, only to discover that it lies elsewhere. And as if that weren't enough, he ends the song in bittersweet fashion, changing the original chorus to reflect this new awareness, wishing them both the happiness that he had once wished for he and his beloved; "And as I go through my life, I will wish her, his wife, all the sweet things they can find." The moral of the story is... Do not read someone else's diary!    


6. Cat's in the Cradle - Harry Chapin

This particular song is the epitome of a classical tragedy, for there is a great deal of irony, not to mention a certain painful lesson that is learned by the father in this tale. This tale of a broken father-son   relationship begins by foreshadowing in the first verse all that is to come; "And he was talking before I knew it, and as he grew he said 'I'm gonna be like you dad, you know I'm gonna be like you." The old expression; "like father, like son", has both a positive and a negative connotation. On the one hand, a child might imitate the virtues of his father, but if he does, he may very well imitate his vices as well. In this case, the prodigal father is breezing through life, setting as his first priority his own wordily success, but in the meantime he leaves little time for his son; "...But there were planes to catch and bills to pay; he learned to walk while I was away." In the next verse he continues this theme; "My son turned ten just yesterday, he said thanks for the ball, dad come on let's play. Can you teach me how to throw? I said not today, I've got a lot to do." The chorus consists of a loose array of nursery like images, culminating with a promise that apparently is never fulfilled; "When you comin' home dad, I don't know when, we'll get together then." The last two verses show the son doing the same thing as his father did (as he goes from college to having a family), and now he too cannot seem to "find the time" for his father. The tragic irony consists of the fulfillment of the son's words at the beginning of the song in a way that hits at the heart of the lesson. The story would be far less of a tragedy had not the father realized too late (presumably) that he had no one to blame but himself for this disconnect. Indeed, after his son gives him a laundry list of excuses as to why he can't see him, the father comes to a painful realization; "And as I hung up the phone it occurred to me, he'd grown up just like me; my boy was just like me."


5. Wish You Were Here - Pink Floyd

Many don't know the fascinating back story to this song. Indeed, most assume that it is about the mere physical absence of a loved one. But what the song is actually getting at is far more disturbing. One of two songs on this list about mental breakdown, Pink Floyd's, Wish You Were Here, concerns a former bandmate named Syd Barrett (he was originally the lead singer), who, due to excessive drug use and a profound disillusionment with the trappings of fame, fell into madness. From this perspective the words of the chorus "...wish you were here" take on a far more haunting tone; "Can you tell a green field from a cold steal rail, a smile from a veil, do you think you can tell... And did you exchange a walk on part in the war for a lead role in a cage." Sadly, the reality is even more tragic than the song suggests, for apparently when they were recording the album, he showed up to the studio unannounced- bald, overweight, and with his eyebrows completely shaved off. Initially no one recognized him. Eventually, however, someone queried as to whether or not this strange apparition was in fact "Syd". It is said that upon seeing him in this condition some in the band actually broke down and wept.


4. You Don't Bring Me Flowers - Neil Diamond and Barbara Streisand

You Don't Bring Me Flowers is a duet performed by Barbara Streisand and Neil Diamond about two spouses/lovers who can no longer communicate as they once did. The lyrics are written from both sides of the relationship, and express in heart rending fashion how each one knows that the other no longer loves them as they once did; "You don't bring me flowers. You don't sing me love songs. You hardly talk to me when you come through the door at the end of the day. I remember when you couldn't wait to love me, you used to hate to leave me." Like a married couple sitting across from one another at dinner- entrenched in an agonizing silence, so this song palpably communicates one of life's great tragedies; a love that has been permitted to die.


3. Eleanor Rigby - Beatles

A song penned mostly by Paul McCartney, this ode to "lonely people" is haunting if only for the fact that it is written about those people that no one writes songs about. The song revolves around a woman named Eleanor Rigby and a priest named Father McKenzie. What can be gleaned from the scant lyrical content is the fact that Eleanor Rigby is what they call a "church mouse", the sort of woman that haunts a church like a ghost. Oftentimes women like this are the de facto caretakers of a church and presumably "picking up the rice" was one of her many unnamed duties. The "rice" it would seem also represents the disparity between the loneliness of her life and the relative joy and comfort of the rest of us. But Eleanor is not alone in being alone, for there is also the celibate Father McKenzie who composes "sermons that no one will hear". There is not much depth in the lyric writing, but McCartney paints just enough of a picture to leave us pondering our own set of lonely people, and asking sorrowfully with him; "All the lonely people where do they all come from? All the lonely people where do they all belong?"      


2. Fire and Rain - James Taylor

Released in 1970, many have speculated about the meaning of this song. However, in several interviews Taylor has explained that the song was inspired by his personal struggle with depression as well as a close friend's suicide; "Just yesterday morning they let me know you were gone. Suzanne the plans they made put an end to you. I walked out this morning and I wrote down this song, I just can't remember who to send it to." Taylor had apparently been out on the road trying to make it in the music business, and his friends, out of a desire to prevent him from becoming too distracted, didn't tell him about her death for six months. What "plans put an end to her" one can only surmise, but if I had to guess I would say that  there were arrangements to send her away for some "treatment"; treatment that seemed to her, for whatever reason, worse than death. Speaking of treatment, another theme that is spelled out in this song is Taylor's own experience in a mental institution. According to an interview, the chorus is about his struggle with drug addiction, but more specifically about the shock treatments he received while institutionalized. Indeed, the "fire" that he describes in the song is not merely a poetical reference to one of his favorite elements, but rather a description of what it felt like to have electricity running through your body. The song itself is a haunting contrast to the spirit of the times, which sought to convince everyone that "free-living" and recreational drug use were the ultimate key to happiness. Mr. Taylor provides a tragic, but helpful, counterpoint.          


1. Same Old Lang Syne - Dan Fogelberg

If ever there were a sad song, this one is it. Whereas the "Boys of Summer" focuses on lost youth, this song is the icon of what lost youth looks like. Written by the recently deceased Dan Fogelberg (R.I.P.), this story is told with the frankness and straight forward lyric styling of a country song; "Met my old lover in the grocery store. The snow was falling Christmas Eve. I stole behind her in the frozen foods and I touched her on the sleeve." OK, it's not Shakespeare, but it makes the story far more believable. You have a girlfriend, you've got a little snow, you've got Christmas Eve, the only thing that's missing is a roaring fire. This could be the beginning of something good, right? "She didn't recognize the face at first, but then her eyes flew open wide. She went to hug me and she spilled her purse, then we laughed until we cried." So far so good. "We took her groceries to the checkout stand her food was totalled up and bagged. We stood there lost in our embarrassment as the conversation dragged." Hmm, sounds like the first sign of a problem. "We went to have ourselves a drink or two but couldn't find an open bar. We bought a six pack at the liquor store and we drank it in her car." This is the first clear evidence that something is amiss in this re-connection with his old girlfriend. There is a good reason that they "drink the beer in her car" (at least from her end)- the woman is married, so obviously she didn't feel comfortable going back to her house. Apart from the questions that could be raised about that, what sticks out most in my mind is how depressing the image of two older adults drinking a six pack in a car is. It is something a bunch of teenagers might do for lack of a better place to imbibe. At any rate, this is consistent with the disillusionment expressed by the woman surrounding her loveless marriage, as well as, he, the musician, who "never had the time to settle down." Nevertheless, as the chorus explains, they are both grasping and groping after some long forgotten sense of romance; "We drank a toast to innocence. we drank a toast to now. We drank to reach beyond the emptiness, but neither one knew how." There is something of the sorrow of all mankind in these words, that sense of life passing you by, that sense that you have lost something that you can never get back, that awareness that even reenacting those old times won't bring them back. Perhaps if one wants to see a glimmer of hope in all this, one should realize that what makes us ache when we experience something like this, is the very thing that suggests that the ache has an antidote- even if that antidote doesn't come in this life. And then as if to put the final dagger in the heart of the listener, Fogelberg writes this last devastating verse; "Our beer was empty and our tongues were tired, and running out of things to say. She gave a kiss to me as I got out, and I watched her drive away. Just for a moment I was back at school, and felt that old familiar pain, and as I turned to make my way back home, the snow turned into rain..." Each line of this last verse could be discussed in detail, but for me the line that is most characteristic of this feeling of loss, is the last one. As a child I loved snow, probably in part because it happened so rarely in the south. Nevertheless, whenever it snowed it was to me like little flakes of manna falling from heaven; it was miraculous. By contrast, the ultimate image of my childhood dreams being dashed was that terrible, almost apocalyptic moment, when the snow, due to rising temperatures, would change back over to rain.



Honorable mention goes to Simon and Garfunkel for "The Boxer," Tracy Chapman for "Fast Car," Billy Joel for "Captain Jack," Mike and the Mechanics for "The Living Years", Phil Collins for "Against All Odds," Skid Row's "I Remember You", and "Circle" by Edie Brickell and the New Bohemians.