“Wreck of the Edmund Fitzgerald” - Gordon Lightfoot
“Life’ll Kill Ya” - Warren Zevon
“Stan”- Eminem
Happens Every Day, by Dar Williams
Seconded.
I tend to play Pink Floyd’s “Brain Damage”/“Eclipse” when I’m in one of my nihilist moods. Mrs. CaptMurdock concurs that PF is one of the most depressing bands ever. She also feels that way about Bowie’s “Space Oddity” and Michael Jackson’s “Ben.”
The theme to MAS*H. “Suicide is Painless.”
Can’t be about love, eh?
That wipes out “Gloomy Sunday” and “He Stopped Loving Her Today.” Both of those are gloomy to the point of death (literally).
You might consider Fats Waller “Black and Blue.” It’s gloomy about race.
Sonora’s Death Row which I first heard by Leo Kottke, but has been done by others.
“Nothing but Flowers,” Talking Heads.
“Tramp the Dirt Down” and “Oliver’s Army,” Elvis Costello. Actually, most of Costello’s early work.
“Discipline” and “Another Blow Against the Evil Empire,” Joe Jackson.
“Ants Marching,” Dave Matthews Band.
Pretty much anything by Warren Zevon.
“Shipbuilding” by Elvis Costello.
“Dancing With Tears in My Eyes” by Ultravox
“Sparrow” by Simon & Garfunkel
Cash’s cover of “Hurt”.
“Blackberry Molasses” - Mista
Pretty sure it was never top 40, but it depresses the hell out of me.
NoClueBoy, the song is simply titled Ohio.
Drive by The Cars.
You Can’t Always Get What You Want by The Rolling Stones
Wish You Were Here by Pink Floyd
Waltzing Mathilda and Sally Maclenan by the Pogues always get me.
what’s that one … isn’t it Sam Stone by John Prine?
Dust In The Wind by Kansas.
Most depressing song ever. Love or no love.
Too bad the songs can’t be about love…I’m kind of partial to
“Something’s Always Wrong” by Toad the Wet Sprocket when I want to be depressed.
Here’s my list:
Doll Parts by Courtney Love
Nothing Else Matters by Metallica
Real Men by Joe Jackson
Smiling Faces by The Undisputed Truth (?)
The Wall by Kansas
For a depressing song that sounds cheeful (like Nothing but Flowers by the Talking Heads), there’s Allentown by Billy Joel
…and for a depressing song about alienation and self-pity, there’s always “Creep” by Radiohead…all though in a way, that song is so over the top, it’s almost laughable.
The Woman Downstairs by The Handsome Family (most of their stuff is pretty depressing)
Waiting For a Train - Jimmie Rodgers (or Merle Haggard or Johnny Cash or about a million others
Nothing by the Fugs (well… it’s kinda funny too)
Living For The Depression by Flipper
“20 Years Ago” by Kenny Rogers.
“Nothing Else Matters” by Metallica.
“Cat’s in the Cradle” by Cat Stevens.
I’m sure I’ll be back with more…