Besides these obvious ones, let me throw out Kinky Friedman's saddest - Ride Em Jewboy Honey, Bobby Goldsboro Ode To Billy Joe. Bobbie Gentry
Contender. Good to see you again, Rosie I know I've changed a lot since then You're lookin' fine, babe Three years, that ain't long, Rosie I still remember our song When you were mine, babe Times change, times change I know But it sure goes slow Down river when you're locked away Hey, why didn't you write, Rosie? I stayed awake most every night Countin' my time, babe Oh no, I ain't mad Rosie I know you had to mind your dad But, just a line babe Oh sure, I remember Ben We went all through school Is that right? Well he ain't no fool He's a good man, Rosie Hold him tight as you can Don't ask me why, babe Yeah, nice seein' you , Rosie Me, I got things to do Well, goodbye babe Times change, times change I know But it sure goes slow Down river when you're locked away
I think John Lennon's "Happy Christmas (War Is Over)" is deeply disturbing. Hits a delicate nerve in me since I was a kid. Totally depressing.
The first songs that come to mind might be by beloved and sadly too-soon-departed brilliant Georgian Vic Chesnutt, on his last 2 albums before he took his like back in 2009 ~ Skitter On Takeoff and At The Cut. I'd say either: "Flirted With You All My Life" or "Coward" might be the saddest songs I've ever heard, at least at this moment in Time. Also: "Feast In The Time of Plague" might be the saddest song for 2020!!
I don't know off the top of my head but Barbara is definitely worth checking out. Here's another one, "le mal de vivre". She was such a character too!
woke for hoops practice on December 9, 1980 at 5am and the top 40 radio played Across the Universe and Ticket to Ride back to back while i wiped away the sleep... uh oh i thought, this is strange...
Wichita Lineman (mentioned above, Glen Campbell)) Into the West (Annie Lennox) The End of the End (McCartney)
Wow, the saddest? some that come to mind- Coldest Day Of My Life[Chi-Lites]... Holly[Smokey]... Beginning Of My End[Unifics]...It Hurt Me Too[The Mad Lads]... Little Boy Blue[The Impressions].
R.E.M. - Everybody Hurts. and I don't own any REM. Janice Ian - At Seventeen. Bonnie Dobson, GOGD - Morning Dew
For me it is Knocking on heavens door, particularly when I remember the scene where Slim Pickens dies with his partner crawling towards him, there is not much sadder than someone dying.
As I sit hear thinking about it, so many more come to mind but I really do have to add "She's Leaving Home" by the Beatles. As the father of a 20 year old daughter, that one just tears me up.
