The Saddest Songs of all Time (Part One)

“Hello dankness my old friend”

Let’s try an exercise in memory for a moment.  I want you to think of your favorite song.  Got it?  Great.  Now, does that song bring you back to a specific time, place, person, or event?  Ruminate on those memories.  Now, think of a song that brings you back to a happier time in your life.  Or, if you’re happy now, just think of a song, I guess.  Then think of a song that brings you back to a darker place in your life.  Got it?  Now here’s the extra credit question: Can you think of a song that does both?  I’d be willing to bet that everyone’s got at least one song like that.

As I explained once before, I’m always more interested in the stories of songs or the meanings behind them than I am about the music itself.  I don’t know why songs sound sad; it may be the chord, key, or instruments, but I can tell you exactly why the lyrics to a song are sad.  Or, alternatively, I can tell you why I find a particular song to be sad, even if it isn’t outwardly so.  And like I hopefully illustrated above, songs that are sad are going to be different for everyone.  Everyone has that song, the one you change the channel on when you’re alone in the car, the one you joke about with your friends but deep down you know it’s painful.  If you don’t have a song like that, you’re either lying to yourself or very, very lucky.

Today I’m going to tell a few stories about songs that I find to be particularly depressing, and hopefully introduce you to some new artists (or at least new songs) along the way.  I’m going to warn you, though I’m looking at the lyrics, a lot of this will have some grounding in my own experiences and how songs bring me back to particular places, so it might get a little real. It’s depressing story time, I guess.

But, anyway, here are what I believe to be the saddest songs of all time.

“Helplessly Hoping,” by Crosby, Stills, and Nash

Let’s start off easy, with a song that doesn’t make me actively want to remove my ears in sadness whenever I hear it.  I don’t know a lot of songs by Crosby, Stills, and Nash, and I only know this one because I saw Annihilation with Natalie Portman, but hot damn is this tear-jerker.

This song is first on the list partially because it’s just about the only one that I find to be sad because of the music, not the lyrics.  The lyrics, I’ll be honest with you, don’t make a lot of sense.  And if they were sung to a different tune, the song would have an entirely different emotional tone to it.  But when you get those sad country chords floating out of Natalie Portman’s lonely record player and the tears that roll down out of her eyes, the words are secondary.  It’s an emotion more than it is a song.  And Annihilation may not be a perfect movie, but it sure as hell knows how to make a mood.

I don’t have a whole lot to say about this one.  It’s the kind of thing where you need to see the movie to experience what I’m talking about.  So, if you can, watch Annihilation.  Or just find that opening scene on YouTube.  But from here on out, it’s more about lyrics than sound, I swear.  Because I’m a creative writing major, not a music major, and I read words.

“Keep me in your Heart,” by Warren Zevon

Okay, here’s something a bit more lighthearted before we start to go into the real heavy stuff.  Warren Zevon, for those of you who aren’t actually middle-aged men trapped in the bodies of college students, is most famous for “Werewolves of London” off of his Excitable Boy album, which later evolved into Kid Rock.  But Warren Zevon, who was pretty prominent in his time, did not have the happiest ending; he died of mesothelioma in 2003, at the age of 56.

That isn’t to say he was unhappy when he died.  Zevon accepted his illness with dignity and chose to die in the way he wanted to.  He knew the end was coming, and he met death with a smile and dry humor.  And he still managed to hold on long enough to see his last album, The Wind, released.

The Wind is really a testament to the kind of person Zevon was; he knew it was going to be his last album and wrote it as such.  Basically the entire album is duets or co-performances with other artists and personal friends of Zevon’s.  These range from Billy Bob Thornton and Timothy B. Schmit to Bruce Springsteen and Tom fucking Petty.  It was an album full to the brim with both folk and rock stars, and most of the songs are pretty excellent, uplifting pieces.  Except for that last song, “Keep me in your Heart.”

Fittingly as the last song of his last album, “Keep me in your Heart” is a sort of review of Zevon’s life, a pledge that even if he’s dead he isn’t gone, and a touching reminder that no one ever really leaves us as long as we still remember them.  It toes the line between quiet hopefulness and reserved acceptance, and it’s the kind of song that doesn’t only fit to Zevon; it’s a one-size-fits-all for lost friends.

“Sometimes when you’re doing simple things around the house / Maybe you’ll think of me and smile. / You know I’m tied to you like the buttons on your blouse: / Keep me in your heart for a while.”  This song isn’t sad because it reminds you of the bad times, but rather it’s sad because it reminds you of the good times that once were and can no longer be.  It’s a funeral piece, more than anything.  And there’s nothing wrong with that.

“Ghost of You,” by 5 Seconds of Summer

Don’t make fun of me, my brother introduced me to the band.  And while 5 Seconds of Summer (or 5sos) may be best known for their songs like “Youngblood” or “She Looks so Perfect,” they have their fair share of downers.  I’m looking at this one and “Amnesia” in particular, because fuck that song.

I don’t listen to songs to feel sad about my romantic relationships or life in general.  I get enough of that without music, anyway.  I really only listen to music when I’m driving or I’m working out, and there’s not a chance in hell that I’m going to break down in tears while lifting weights.  So I pass on sad songs, usually.  I opt for something more uplifting, like “Ganglplank Galleon,” because I like to imagine music videos for songs while I run.  So it’s been a while since I’ve willingly listened to any of these songs.

Usually my brother or mother will force songs like “Ghost of You” upon me because they say it’s unnatural for me to want to “avoid emotions” or not want to “feel things.”  They tell me that this music is cathartic and good for me, a way to relieve pent-up stress or face those demons I’m keeping deep inside.  But I’m perfectly okay with not making myself sad on purpose.  And this song could make anyone sad on purpose.

One of the cardinal rules of story-telling is to “show, don’t tell,” and of all the songs I know, this one does one of the best jobs of showing.  It doesn’t outwardly say anything about the narrator or his past relationships.  There’s no purple prose of the pain deep in his heart or the anguish in his mind.  There’s just images.  Things like “There’s your coffee cup / the lipstick stain fades with time.” Concrete details, remnants of something dead and gone, something that every listener can probably relate to.  We all images like this in our life, something specific we associate with those broken things we hide in the closets of our minds.  And those images are the most depressing.

The song is the narrator sharing those images with us, those ideas that remind him of what he once had, the things he once felt.  The song doesn’t openly say whether the narrator’s significant other died or broke up with them, but I think it’s way more depressing if they died.  To have someone yanked out of your life so unexpectedly is thankfully a process I only have second-hand experience with, but I’ve thought about it enough to have some ideas of what it might be like.

And I think the chilling last lines of this song sum it up pretty well; “And I chase it down / with a shot of truth / that my feet don’t dance / like they did with you.”  They’re gone.  You can’t get them back.  And no amount of grief can change it.

There are a lot of songs that talk about that.  “Landslide.”  “Travelin’ Soldier.”  “Tears in Heaven.”  Hell, even Hamilton’s got “It’s Quiet Uptown.”  All these songs make me sad.  But I only have the emotional resistance to talk about one before I have to actually start feeling things, so I chose this one since it has the most views on YouTube and it should (statistically) get me the most clicks.  And to think I started this post thinking it would be funny.

“Photograph,” by Ed Sheeran

Okay, most of you are going to look at this entry and think, “Hey, this isn’t a sad song!  It’s all about the power of love and how it can cross any distance of time or space, and that as long as your heart is true, love covers all barriers and transcends pain.  Love makes life worth living!” And while all that is true, I assure you that you are wrong. It’s the saddest song of all time.

I personally kind of hate Ed Sheeran.  Not as a person; I’m sure he’s a wonderful human being, and I’d be his friend if I could.  But I don’t listen to music to feel things other than excitement or energy or happiness.  And every single Sheeran song makes me feel everything but those things.  They make me feel nostalgic.  I’m looking at you, “Castle on the Hill.”  Or they make me feel hopeless.  Hello, “The A Team.”  But none of them make me feel so crushingly lost as “Photograph.”

Of all the songs on this list, “Photograph” makes me feel the most emotions, and to understand why, I think I have to take you back to upstate New York, the summer after my junior year in high school.  I was on a short exchange trip through my high school’s AFS club.  Don’t ask me what AFS means, I couldn’t tell you.  Even though I was the president for both junior and senior year.  But, anyway, we hosted kids from rural northern New York in our town in Illinois, and then we visited them a few months later.  It’s supposed to help us connect to new friends and see other parts of the country.  And also, apparently, to break your heart.

Let me set the scene: It was our host high school’s last week of school, and we were at their talent show.  My school was already out, and two of my closest friends had just graduated.  They were on the trip to New York with me, and were in fact sitting next to me in a crowded auditorium of two hundred kids I didn’t know at a school I didn’t go to.  So we’re sitting there, at this end-of-the-year variety show, and they intersperse the different acts and prizes with slideshows of pictures and videos of the kids in that school as they grew up.  Baby pictures, elementary school recess, middle school dances, stuff like that.  And all these slideshows have that typical sappy music, the wordless guitar chords and piano riffs.

So I’m watching these kids grow up in front of me, after a fashion, and I realize, dang, I’m going to be in this same position a year from now.  And then I think, dang, my best friends already went through this and now things will never be quite the same as they were.  I’m starting to get tearful, because the person sitting next to me was perhaps the one human in the world I felt closest to that wasn’t related to me by blood.  One of the few people not related to me that I could say “I love you” to and it wouldn’t be weird for either party.  And now she was about to step out of my life.

This isn’t true, exactly.  We go to the same university now, and see each other pretty often, so things are good, but I didn’t know that at sixteen.  So you can imagine the kind of head space I was in at that time.  And then the next talent section comes up, and Ed Sheeran pops into the room.

Not really.  It was a girl playing Ed Sheeran’s “Photograph” as her talent show act, but that song is eternally etched into my brain as the first time I broke down crying in a public place.  Sure, it was dark and the only people who noticed me were my two friends next to me, but it was different than crying at home.  It was too much to contemplate this massive change in my life while hearing things like “We keep this love in a photograph / we made these memories for ourselves / where our eyes are never closing / hearts were never broken / and time’s forever frozen still. / So you can keep me / inside the pocket of your ripped jeans / holding me closer ‘til our eyes meet / you won’t ever be alone.” “Wait for me to come home.”

Good Lord, I can’t even read the words without tearing up a little.  For me, that song became a representation of a pivotal point in my life.  A point when I realized, I think, that the world isn’t a Hallmark movie.  The people you love may not always love you back.  Those you care about most aren’t always the ones that can stick around.  And sometimes the most dangerous monsters are the ones we keep inside.

Now, I should clarify that last point with a statement; these fears of lost friendship and intense feelings of human emotion aren’t the only reason that I was having such a hard time in that auditorium.  There were other things, too.  I’d even go so far as to say that this occurred right around the lowest point in my life, though all things considered I’ve been pretty damn lucky in that I haven’t had it go lower before or since.  I’ll explain more about that next week, since I don’t have time or space here. Keep an eye out for part two.

Anyway, my other close friend, the sister of the one I now go to school with, was also crying during this song.  I like to think it’s for similar reasons, since we were all going to be split up now and things wouldn’t be the same.  So we hugged each other and commiserated in our twin sadness.  And my best friend looked on at us, confused why two teenagers were bawling their eyes out in an auditorium of strangers over a clichéd pop song.  Though, looking back, it might also have had something to do with the fact that there was an “in memoriam” section for a deceased classmate at the end of the talent show.  But that isn’t my story to tell.

I guess I can’t really hate Ed Sheeran, because I took his words to heart.  I still keep a photo of that trip on my phone.  Even all these years later, it’s still there.  And I can look at it and see our smiling faces, of that time that once was.  I remember what an incredibly fun trip that was, but also how bittersweet it was, too.  And I didn’t even tell you the full story, because some of it is about stealing from the Amish. I’ll get to that some other time.

I forget, sometimes, just how much this song affects me.  I try not to listen to it, ever.  My brother torments me with it (in good spirits) by playing the song in the car when he drives.  It’s become a long-running joke in my family about how visceral of a reaction I tend to have to the opening notes.  But I keep those feelings in a photograph on my phone in my pocket.  It’s as close to my heart as I’ll let them get, because it’s a reminder that we don’t always move on.

Oh, boy, I’m glad that’s over. I was going to keep writing about other songs, and I have a bunch more, but I realized as I kept writing that I had reached my emotional quota (and word count) for the day, and I decided that I didn’t want to talk about some of the other songs yet.  But I still believe they’re stories that need to be told, I just don’t have the emotional capacity to tell them right now.

And when I was going back over this list, categorizing all the songs that I wrote about today, I found that they all have a similar theme; grief and loss.  They’re all about loss, loss of a loved one, be them a friend, lover, or family member.  Either the slow loss of “Helplessly Hoping” or “Keep me in your Heart,” the sudden loss of “Ghost of You,” or my very personal, anticipated loss of “Photograph,” each of these songs was kind of about the same thing.  And I didn’t even mention Bastille. Next week, the songs will also be about one general theme.  It just won’t be loss.  It will be… Well, it won’t be a happy post.  I’ll say that much.

Which is why I’m saving my meme songs for the end of that, because I’m going to need some memes after I write that all down.  Here’s something that should hopefully tide you over until then.