We’re talking about “saddest country songs” over at MCB. Since the only country songs I know are Johnny Cash, Loretta Lynn and Dolly Parton I’m out of the running pretty early.
But then someone brought up Dan Fogelberg’s Same Old Lang Syne, which got me to thinking.
Isn’t that essentially the same song as Harry Chapin’s “Taxi”? With beer instead of pot, of course.
Just Another Pretty Farce 
I’m not sure if this is a country song, but Harry Chapin’s “Cats in the Cradle” gets me every time. It used to be I couldn’t even listen it. It makes me want to go run and hug my dad, and we’ve even always been pretty close…
As far as I’m concerned, Little Jimmy Dickens’ “Raggedy Ann” is the saddest country song ever. I used to call the radio station when I was a little girl and request it and cry and cry. 😉
Beloved Wife, by Natalie Merchant.
I forgot. George Jones’ “He stopped loving her today”.
Definitely.
“He Stopped Loving Her Today” was my dad’s favorite song to sing. Makes me bawl every time.
Dolly Parton Jeannie’s Afraid Of The Dark {you tube}
Wildwood Flower always gets to me.
Barry – Johnny Cash covered “Cats in the Cradle” and succeeded in making is ever sader. Check it out….
cash’s covers of “southern accents” and “oh danny boy” are about as sorrowful (and beautiful) as anything i’ve ever heard…perhaps not “sad” exactly, because there’s a sense of transcendence – or maybe redemption – in both…definitely deeply melancholy though
I cry when I hear “Comfortably Numb” by Pink Floyd. Guess I found out why I listen to so little country, though a good dose of Dwight Yoakam now and then is fun.
Bob
And while we’re on the subject of my dad’s favorite songs — Wildwood Flower was his favorite one to play on the guitar. Dang, he had depressive tastes. I never really thought about that before.
Just heard on one of my CD’s “Leader of the Band” by Dan Fogelberg.
http://www.danfogelberg.com/leaderoftheband.html
-Bob