Sad songs- We love them- We need them

"Jolie Louise"  Daniel Lanois

"Pancho and Lefty" Willie Nelson & Merle Haggard

"Goodbye"  Steve Earle

"Sam Stone"  Johh Prine

(I am absolutely positive that Hair Of The Dog/Nazareth & "My Boyfriends Back"/The Angels should definitely get honorable mention; however that maybe the  Testors talking.  I may reconsider after I sober up.)

I would also add "Tecumseh Valley" by Townes" Van Zandt,

& perhaps

"Waiting Around To Die" by the same artist.

As my memory was jogged to think of Townes, maybe I would consider adding

"Fort Worth Blues"/Steve Earle.

Maybe.

"Dead Babies" Alice Cooper

"Speed Of The Sound Of Loneliness"   John Prine.

When we lost John Prine, we lost a great one.

"Lonelier Than This" Steve Earle

"Me And Bobby McGee" whether performed by Kris Kristofferson or covered by Janis Joplin

"The Last Resort" The Eagles

"Carmelita"  as performed by Warren Zevon or as covered by Linda Ronstadt

"Gloom, Despair, And Agony On Me"  Hee Haw

"The Ballad Of Dwight Fry"  Alice Cooper

From back in my days of high school angst, Nazareth's version of "Love Hurts."  (Although I don't think it would have an effect on me any longer.)

"The Ghost Of Phil Sinclair" by Chip Taylor still evokes an emotional response (of sorts) from me.

"Hurt" by Nine Inch Nails as opposed to the cover of it that Johnny Cash did.

From Lucinda William's "Sweet Old World" CD, the song "Sweet Old World" and also from that DC, "Pineola."

I really liked the covers that Emmy Lou did of "Sweet Old World," and also her cover of Steve Earle's "Goodbye." 

"Daniel"  Elton John/Bernie Taupin

"Accidentally Like A Martyr" Warren Zevon (The hurt gets worse and the heart gets harder)

"I Feel Like A Bullet (In The Gun Of Robert Ford)" Elton John/Bernie Taupin

Although "Daniel" from "Don't Shoot Me, I'm Only The Piano Player" is the saddest-for-me Elton John Song (possibly due to personal family events we were experiencing back then), "Blues For Baby And Me" off the same album always stuck me as melancholy.  As did "Rocket Man," also by John/Taupin. 

@switzer145 another vote for "Sweet Old World"! Yes!

However, as much as I like Emmy Lou’s cover of it, I am prejudiced and I love the original by Lucinda Williams.

"Everybody Hurts"  REM

From the "Human Remains" CD, "Little Sandy"  Terry Allen

"Put The Bone In" Terry Jacks.  (This was actually on the flip side of "Seasons In The Sun.")