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Some of my favorite saddest country songs are Concrete Angel by Martina McBride, Jesus Take the wheel by Carrie Underwood, In my Daughter's Eyes by Martina McBride.
George Jones: The Grand Tour
Lefty Frizzell: How Far Down Can I Go?
Patsy Cline: Crazy
Hank Williams: Weary Blues from Waiting
What about yours?

I think the saddest circumstance I've ever heard a country song done is the scene in Tender Mercies when
Mac(Robert Duvall) learns that his daughter(Ellen Barkin)has died in a car crash. Duvall sang "On The Wings
of a Dove" and it's him singing it. With his back to the camera, he looks out a great big window and sings the song
(to his daughter's memory). As he sings it, you know exactly how he feels. The song itself is not sad, its actually
a celebration of one man's faith in God and His Son Jesus...".God sends us His love, on the wings of a dove". I'm
not religious(I don't celebrate the Lord in a church or belong to a denomination)but this song is very inspirational
and my favorite country song.
I think the saddest country songs were written by Hank Williams(Your Cheating Heart and
I'm So Lonesome I Could Cry) He was certainly the most talented. He was in a lot of pain
the latter years of his life as a result of injuries sustained in a car wreck and I think the
pain showed in much of his music.

There are several. One was a little-known song by Jimmie Rodgers who did Honeycomb back in the 60's. The flip side of one of his hits was one called The Little Dog That Cried. A real tear-jerker about a little dog that was present at the Crucifixion. Another one was Nobody's Child by Hank Snow. Also Mary Dear by Gene Autry was a sad one about a guy who comes back from the war and finds his sweetheart dead. Vernon Dalhart's Letter Edged in Black, Dickie Lee's Patches, altho that may not be exactly country. My brother-in-law was a horrible singer, but when he was drunk he would sing Patches and bring tears to your eyes. When I was about 6 or 7 years old we had a record of You Are My Sunshine by Bing Crosby and every time I heard it I would bawl like a baby. I dont know why, its not really a sad song but there was something about it that would turn on the waterworks.

Marty Robbins singing "They're Hanging Me Tonight" and Johnny Cash's "The Man Comes Around".

Another one I just thought of was one called A Soldier's Story, it was from The Good, The Bad, and the Ugly. It was in the scene where Eli Wallach was getting the crap beat out of him in the Union prison. Where that one guy was playing the violin and the prison guard told him to play with more feeling, you could see the emotion in the violin players face. That is one sad song.

Dolly singing "I Will Always Love You"
Patsy Cline singing just about anything
Willie-"You Were Always on my Mind"
Carrie Underwood- "Just a Dream"
Darius Rucker-"Don't Think I don't Think About It"
Johnny Cash-"Hurt"

Bury Me Not - Vernon Dalhart
When the Works All Done This Fall - Tex Ritter
Mary Dear - Gene Autry
Gallows Hill - Billy Lee Riley
Billy Venero -Traditional
Hobo Bills's Last Ride - Jimmie Rogers

great thread.................Toby Keith, American Soldier

The song that never fails to make me cry is
Johnny Cash - The Ballad of Ira Hayes

Help me make it through the night...Sammi Smith...one of my faves...

Old Shep by Red Foley. Surprised no one mentioned that one.
Shennadoah - Tex Ritter
Somewhere Along the Line - Eddie Dean

Pancho & Lefty - Willie Nelson and Merle Haggard
Boulder to Birmingham - Emmylou Harris
and what about:
American Pie - Don McLean

Forgot about Emmylou Harris...one of the truly amazing ones

Don't Know if she counts as country but Kate Smith singing How Great Thou Art, gives ya goosebumps

She is His Only Need- Wynonna Judd
Seven Spanish Angels- Ray Charles and Willie Nelson
He Stopped Loving her Today- George Jones

One I heard today. Little Joe The Wrangler by Montana Slim.