To view the Top Ten Songs, go here.
11. “I’m So Lonesome I Could Cry”
Written and recorded by Hank Williams. Released 1949.
A nearly surreal weeper, Hank Williams’ evocative ballad utilized language in a way that was completely new for its country music time, and completely influential in ours. “The silence of a falling star lights up a purple sky/And as I wonder where you are, I’m so lonesome I could cry.” It’s not the flash of the star that wounds doomed Hank, it’s the silence.
12. “Rosalie’s Good Eats Café”
Written by Shel Silverstein. Recorded by Bobby Bare. Released 1973.
In eight minutes (yes, eight, because that’s what the song needed), Silverstein gives us a detail-rich portrait of a sadsack diner in the hours after late night becomes early morning. The little restaurant holds a petty thief of a short-order cook who was once a rodeo star. It has a pregnant woman who prays from her booth, a randy guy in a tux, a baby-faced sailor, a disaffected couple, a hippy, a waitress who paints her nails blue and a kind-hearted proprietor. Oh, there’s a wino as well. Silverstein weaves all that together and delivers a winning story and a subtle but palpable message about hope and desperation.
13. “Coat Of Many Colors”
Written and recorded by Dolly Parton. Released 1971.
Parton’s matter-of-fact determination, innate intelligence, empathy and confidence are all on display as she writes of the rags her mother sewed into a coat for the winter.
14. “Dang Me”
Written and recorded by Roger Miller. Released 1964.
Either the funniest sad song in country music history, or the saddest funny song in country music history. The “I lack 14 dollars havin’ 27 cents” line is genius. The part about drinking at the bar while his wife sits home with a month-old child cuts close to the bone.
15. “Whiskey Lullaby”
Written by Jon Randall and Bill Anderson. Recorded by Brad Paisley and Alison Krauss. Released 2003.
Bill Anderson was 45 years into his songwriting career when Paisley and Krauss recorded this dark and compelling gem. Hard to believe a song with two deaths and the line “He put that bottle to his head and pulled the trigger” was allowed on country radio. It’s not true that great songs always find their way to the public. It is true that great songs sometimes do, though.
16. “Mr. Bojangles”
Written by Jerry Jeff Walker. Recorded by the Nitty Gritty Dirt Band. Released 1970.
A sharp character study of a dancing prisoner. Walker lets us into a New Orleans cell, which turns out to hold the best show in the world. “He let go a laugh and shook back his clothes all around” is an achingly precise line.
17. “He Stopped Loving Her Today”
Written by Bobby Braddock and Curly Putman. Recorded by George Jones. Released 1980.
Braddock and Putman arrived at a perfect title and premise, and then they wrote the hell out of it. And then they went back and rewrote. “Nobody will buy that morbid son of a bitch,” Jones told producer Billy Sherrill, who helped Braddock and Putman with the rewriting process. The song wound up as a Grammy-winning savior for Jones, who wrote in an autobiography, “A four-decade career had been salvaged by a three-minute song.”
18. “Rain Just Falls”
Written by David Halley.
Recorded by Jimmie Dale Gilmore. Released 1988.
No idea why this gorgeous weeper hasn’t been recorded by dozens of right-thinking country artists. Could be Willie Nelson’s old “sad songs and waltzes aren’t selling this year” deal. In Halley’s song, sadness and longing are both mysteries and unavoidable truths. “It ain’t on your account that I’m leaving, if I’m leaving,” he writes. “Rain don’t fall for the flowers if it’s falling/Rain just falls.”
19. “Funny How Time Slips Away”
Written by Willie Nelson.
Recorded by Billy Walker. Released 1961.
Twelve lines, no chorus. And a snarling, poetic rebuke at the end of what seemed until line number 11 to be a perfectly civil song. “In time you’re gonna pay,” Nelson writes, before concluding, “And it’s surprising how time slips away.”
View #20-50 on pages 2-4 below.