Kidnapping, Murder, and Mayhem

The 11 Saddest Country Songs of All Time

by Robert A. Waters

Rolling Stone magazine recently released what it called the “40 Saddest Country Songs of All Time.” On the premise that “even a blind hog finds an acorn once in a while,” they found a few good ones. Unfortunately, there were too many modern-day songs and not enough older and alternative tunes. Those who have read my blog for very long know that one of my passions is old-time hillbilly music. It's what I grew up hearing and what I still listen to. So here are 11 songs the Rolling Stone article left out.

The Sun Comes Up

Hank Williams III

Hank III does his best to live up to his grandfather's name. Hard living, hard drugging, and hard drinking seems to be the norm of the Williams clan, but they have country music embedded in their DNA. This song is straight country, and straight-out sad. No wonder it never made a blip on the modern CMT charts.

Lost Highway

Hank Williams

Written by the blind country songwriter, Leon Payne, this song is the defining statement about Hank's life. It's ironic since Hank wrote most of his own songs. In many religious songs, there is redemption for sin, but in this song, there is no redemption—the singer is going straight to Hell. This is real country music written by real country people who had, fortunately, never heard “Imagine” by the Beatles.

After the Fire Is Gone

Amber Digby and Justin Trevino

These Texas-based singers nail this old “cheating” song. Their version has the feel of, shall we say, authenticity. In other words, it sounds like they've been there, done that (not saying they have, just saying the song has that “feel”). Written by L. E. White, numerous country stars have recorded it, including Loretta Lynn and Conway Twitty, Willie Nelson, and Tanya Tucker. But their versions are too commercial. I like the Digby and Trevino raw, gritty version best.

Born to Lose

Johnny Cash

Ted Daffan, a honky-tonk singer and songwriter, penned this song in the 1940s. It's been recorded by more than 100 country singers, including this version by Johnny Cash. “Born to lose, I've lived my life in vain/Every dream has only caused me pain...” Any song with those opening lines has to be sad and has to be country.

Leona

Stonewall Jackson

Rolling Stone would NEVER admit that a descendant of the great Southern General Thomas Jonathan “Stonewall” Jackson could be a great country singer. But that he is. “Leona” is written from the perspective of a cuckolded husband and the tragic conclusion is right out of today's headlines. Stonewall Jackson, the singer, had many hit songs, including “Waterloo,” which crossed to the pop charts. Written by the well-known Nashville songwriter, Cindy Walker, “Leona” never became a hit, but is still one of my favorites.

Down Where the River Bends

Dwight Yoakam and Ralph Stanley

Penned by country songwriters Jack Anglin, Johnny Wright, and George Peck, this song is about a soldier going off to war. If he comes back, he is reminded to meet his sweetheart “down where the river bends.” Dwight Yoakam and Ralph Stanley perform this bluegrass version of the song, and Stanley's high tenor is guaranteed to send chills down your spine.

Cold Cold Heart

Hank Williams

Written by Hank, this song became a number one country hit for him, then crossed into the pop charts to become Tony Bennett's first number one song. Hundreds of singers have recorded it, and the song has become a standard, usually delivered with minimal feeling.  Not so, Hank's version.  The pain of his loss is raw and vicious and we know there'll be no happy endings here.  (How Rolling Stone could miss this song, I don't know.)

Lord, I've Tried Everything But You

Vernon Oxford

This song is a lament about a life gone wrong by the singer who was called “too country for country music.” While modern “country” singers listen to the Beatles, the Stones, Jimi Hendrix, and rap, Oxford cut his teeth on real hillbilly music—mostly Hank. God is the last resort for many a former reprobate, and the title of this song says it all.

San Francisco Mabel Joy
Mickey Newberry

Any songwriter who can come up with a title like “She Even Woke Me up to Say Goodbye,” has to be good. Add to that “San Francisco Mabel Joy,” about a Georgia boy who falls for a prostitute, kills her lover, and ends up doing 99 years in prison, and you've got the makings of real country music. It's a long, rambling song that could never make it onto the country music charts.

That Old Time Feeling
Guy Clark

Texas singer/songwriter Clark begins this song with these lines: “That old time feeling goes sneaking down the hall/like an old gray cat in winter keeping close to the wall...” Need I say more?

Your Cheatin' Heart

Hank Williams

This is arguably the greatest country song of all time. Hank allegedly wrote it about his cheating wife, Aubrey. Of course, the cheating was mutual, but... This song has been recorded by almost every country singer in history. The pain is palpable as Hank sings, “Your cheatin' heart will tell on you.” Hank, who grew up dirt-poor in Alabama, achieved fame and fortune beyond his wildest imaginings, but was tormented by physical and emotional pain all his life. His songs have been recorded by almost all country singers, and many pop crooners. Going barefoot while selling peanuts during the Depression, he could never have imagined the musical influence he would exert. The writer of the Rolling Stone article should be canned for not including this song.