Most Depressing Songs You've Heard

[tarallucci]

 

[Latimer]

Hank Williams: I'm So Lonesome I Could Cry

 

[Latimer]

Streisand's version of Cry Me A River sounds not simply vengeful but desperate:

 

[Latimer]

Jacques Brel: Ne me quitte pas:

 

[gsdx]

I've been here. Perhaps you have, too.

 

[Latimer]

^
Thank you. Best version I've heard and seen.

 

[Latimer]

She would know:

 

[willhunt]

I"d heard this covered by everyone. I'd heard it by Clapton. When I learned the backstory I was heartbroken.

 

[OlderNerd]

A few off the top of my head: Puff the Magic Dragon, Wreck of the Edmund Fitzgerald, One Tin Soldier, Cat's in the Cradle.

 

[Charon]

The Cure have their fair share of depressing songs too.

 

[PalacePaul]

Wow, I didn't remember Puff the magic dragon. This made me cry some times over the years.
This one makes me sad, too:

 

[FPNY]

I've been here. Perhaps you have, too.

Well, that’s pretty much made me a blob of withering, sniveling manliness in my own dining room...wow...

 

[72-Jay]

Some of the stuff by Red Sovine is pretty depressing..

 

[gsdx]

I"d heard this covered by everyone. I'd heard it by Clapton. When I learned the backstory I was heartbroken.

The back story - a little tough to watch and even sadder than 'Tears in Heaven':

https://www.youtube.com/watch?v=-gbDPJTPYNs

 

[TickTockMan]

 

[Thad1527]

In 1923, Mr. Ernest Newman (apparently a respected critic of the time) referred to this song as the worst song ever. It has not improved with time.

Makes me want to jump in the casket and close the lid.

 

[herry1]

Keep It Part 2 (Inferiority Part 1) - Dexys Midnight Runners