Some of the Saddest Songs I've Ever Heard

I thought this would be a fast topic and let me get back to my novel revision that I aim to have done by Friday, but I was wrong. Regardless, because the emotions we regard as "negative" are in most cases healthy normal requirements to be a healthy normal human, it can be very therapeutic to embrace them sometimes instead of trying to pretend they don't exist. These songs hurt me, but I love them. Not every song can be "Walking on Sunshine". I have excluded breakup/unrequited love songs from this list to prevent it from exceeding eight thousand entries, and instead focused on some of the other crap that life has to offer. Enjoy.

Bill Mumy - The Ballad of William Robinson

Being lost in space forever is a special kind of depressing, though if he gets to keep visiting actual planets and having adventures I don't know what he's complaining about.

Green Day - Boulevard of Broken Dreams [Explicit]

I currently live on Kip Thorne Boulevard, which became a boulevard of broken dreams when I moved here a couple months ago.

Harry Chapin - Cat's Cradle

The only thing sadder than missing opportunities is growing up.

Loreena McKennitt - Dante's Prayer

A song that will doubtless by repeated on my upcoming list of songs I want included in the new Latter-day Saint hymnal.

Genesis - Dreaming While You Sleep

I honestly thought the lyrics of this song were some kind of artistic metaphysical nonsense until I actually paid attention to them and was like "Holy crap!"

Kansas - Dust in the Wind

Even if you, like me, believe in immortal souls and another life that will suck considerably less than this one, the reality check of how temporary and insignificant humans are can be sobering.

Tracy Chapman - Fast Car

A song, introduced to me years ago by my friend Cece, about how poor people deserve to have crappy lives because obviously if they just pulled themselves up by their bootstraps they would be fine (sarcasm).

Shankar-Ehsaan-Loy - Heartbeat (Instrumental)

Knowing the plot of the movie makes every song from the soundtrack melancholy, but this one really tests the limits of how beautifully (I can't stress that enough) soul-wrenching an instrumental piece can be.

Billy Joel - Leningrad​

"Storm Front" is my favorite Billy Joel album, and most of the songs on it are criminally underrated, including this one.

Suzanne Vega - Luka

Not just the abuse per se, but the resignation and broken spirit really drive this one home.

Stephen Moore feat. Kimi Wong - Marvin, I Love You

Okay, I lied, and don't have the heart to refuse entry to this breakup/unrequited love song by everyone's favorite manically depressed robot, accompanied by an irrelevant cute video.

Nightwish - Nemo

"Nemo" means "no one" and if that's not cause for introspection I don't know what is.

Alanis Morissette - Perfect

With her unique voice and interesting liberties with pronunciation and scansion, Alanis comes across as a very real person singing about real issues, like impossible expectations from parents or authority figures.

Mika - Rio

Again, upbeat but not upbeat, illustrating low self-esteem and the perceived futility of trying to change things, but in a way you can dance to a little.

Simon & Garfunkel - The Sounds of Silence

...

Kitaro - Symphony of the Forest (Instrumental)

As I've mentioned before, this song gave me my first experience with depression and loneliness when I was three or so, and now I listen to it just to show it who's boss.

Matchbox 20 - Unwell

Only I and a few hundred million other Aspies have adopted this as our unofficial theme song.

Bruce Hornsby & the Range - The Way it is

Somehow this song is upbeat but not upbeat, even without getting into the subject matter of racism and civil rights.

Scorpions  - Wind of Change

The fall of the Berlin Wall was a joyous occasion for most, but this hardly comes across to me as a joyous song, probably because it's reflective and nostalgic instead of celebratory.

Madonna - You Must Love Me

Eva Peron sings about her husband staying by her side as she dies of cancer (which isn't a spoiler because the musical literally starts with her death and goes into flashback for most of the next two hours).