A CBC show called “As It Happens” recently asked listeners to name what they thought was the most depressing song of all time, ever. In honor of this depressing time of year, don’t ya know.
Well they had interesting responses - “Gloomy Sunday”, “Where have all the Flowers Gone”, “Boulevard of Broken Dreams”. - I’d like to read the responses from the posters on this message board. I know there have been similar threads, but the catch and the hard part is you only get to name one. No hedging by saying either “Strange Fruit” or “Streets of London” or “If you see her say hello”. Only one, the most depressingest. Have at it.
Oh, I think Harry’s got some more depressing songs. (Not necessarily good songs, mind you). Like, “The Shortest Story”, told from the point of view of a baby who dies of hunger at the age of 20 days. It ends with the eternal question, “Why is there nothing, now, to do but diiieeee?”
As far as most depressingest, I’m not sure. Maybe “Paradise” by Bruce Springsteen, off The Rising
Hurt. The original NIN version is plenty depressing, but Johnny Cash’s cover is 10x more so.
You could also take your pick from just about any song in Elliott Smith’s discography - though for me it’s always been Pitseleh (mostly because of where/when/how I first heard the song, rather than just the lyrics… which are plenty sad in and of themselves)
Keep me in Your Heart For A While by Warren Zevon is pretty f-ing depressing, but when you listen to it and know that he KNEW he was on his deathbed, and this was his last album…it’s heartwrenching.