A few times in the last couple of weeks when I would play certain songs on the radio I would say things like, “if I were to have a top 5 list of the saddest country songs ever written this ‘song’ would make the list.” Usually it would be Gene Watson’s “Farewell Party” or George Jones’ “He Stopped Loving Her Today.” Finally I decided to create my own personal rank of the Top Ten Saddest Cryin’ In Your Beer Country Songs, classic and not-so-classic. This is my own personal list and not influenced by any national rankings.
What classifies a Cryin’ In You Beer Country Song in Derik Wayne’s mind? I feel my formula is rather simple. First, there has to be a broken heart caused by lost love, whether from divorce, break-up, or worse. Second, the sadness has to be so great the individual that’s broken can’t even stand to look at himself in the mirror or takes the pain to the grave.
10. “What I’d Say” – Earl Thomas Conley
Written by Robert Byrne and Will Robinson. The song talks of a man holding imaginary conversations with the woman who’d left him, rehearsing what he might say if he ever ran into her. He doesn’t know whether he would express his feelings, compliment her, or tell her to “go to hell.” The song concludes by the man stating that his ex-lover would have to wait until the day they meet again to find out what he would say to her.
“Your lookin well
Or go to hell might be what I’d say”
9. “I’m Over You – Keith Whitley”
Written by Tim Nichols and Zack Turner. A break-up is never easy, especially when mutual friends are involved.
“You heard I’m drinkin’ more than I should
And I ain’t been lookin’ all that good
Someone told you I was takin’ it rough
Why they makin’ those stories up
When I’m over you?”
8. Statue Of A Fool – Jack Greene/Ricky Van Shelton
In 1969, it was recorded Jack Greene, released as a single and became a number 1 hit. In 1989, it was recorded by Ricky Van Shelton. We’ve all let something good slip through our hands at one time or another.
“Somewhere there should be
For all the world to see
A statue of a fool made of stone
The image of a man
Who let love slip through his hands
And then just let him stand there all alone”
7. Legend In My Time – Don Gibson/Ronnie Milsap
Written and recorded by Don Gibson in 1960. The song was recorded by Ronnie Milsap and released in November 1974. Nothing like admitting your regrets and you can tell Don had some when he wrote this amazing song.
“If heartaches brought fame in love’s crazy game,
I’d be a legend in my time.
If they gave gold statuettes for tears and regrets,
I’d be a legend in my time.”
6. I Never Go Around Mirrors – Lefty Frizzell
Written by Sanger Shafer and Lefty Frizzell. Only a handful of artists were born with the ability to sound like they’re “crying” when they’re singing. Lefty is one of them.
“So I never go around mirrors
I can’t stand to see me
Without you by my side
No, I never go around mirrors
Because I gotta heartache to hide”
5. Whiskey Lullaby – Brad Paisley & Alison Kraus
Composed by Bill Anderson and Jon Randall. Its narrative centers on a couple that has an abruptly painful separation leading both to alcoholism and eventually drinking themselves to death: first the man, with a broken heart, and later the woman, feeling guilt for the man’s death.
“He put that bottle to his head and pulled the trigger
And finally drank away her memory
Life is short, but this time it was bigger
Than the strength he had to get up off his knees
We found him with his face down in the pillow
With a note that said, ‘I’ll love her till I die.’
And when we buried him beneath the willow
The angels sang a whiskey lullaby”
4. “Farewell Party” – Gene Watson
Written by Lawton Williams in 1960. Little Jimmy Dickens recorded the song in 1961. It was also recorded Gene Watson in February 1979. Watson’s version is the most well known. This song has the whole package. Great production sound, sad lyrics, and a “cry” in Gene’s voice. Who can forget the ironic final high note he hits at the end.
“When the last, breath of life
Is gone from, my body
And my lips, are as cold as the sea
When my friends gather ’round
For my farewell party
Won’t you, pretend you love me”
3. “He Stopped Loving Her Today” – George Jones
The song was written by Bobby Braddock and Curly Putman and tells the story of a friend who has never given up on his love; he keeps old letters and photos from back in the day and hangs on to hope that she would “come back again”. The song reaches its peak in the chorus, revealing that he indeed stopped loving her when he died and the woman does return—for his funeral.
“He stopped loving her today
They placed a wreath upon his door
And soon they’ll carry him away
He stopped loving her today”
2.”Chiseled In Stone” & “Is It Raining At Your House” – Vern Gosdin
Number two features a “tie” between two songs by Vern Gosdin. Both of these songs left me in the tears the first I heard them both. Vern stumbled upon some incredible song writing!
“Chiseled in Stone” is co-written by Vern and Max D. Barnes.
“You don’t know about sadness
Till you’ve faced life alone
You don’t know about lonely
Till it’s chiseled in stone”
“Is It Raining at Your House” is co-written Vern, Dean Dillon and Hank Cochran.
“Is it raining at your house like it’s raining at mine
Do you miss me like I miss you, is it cloudy all the time”
1. “I’m So Lonesome I Could Cry” – Hank Williams Sr.
Written and recorded by Hank in 1949, is by-far one of the saddest songs ever recorded. Between the lyrics and the way Hank sang it, ranks this as number one my list. You can feel his sadness with every note.
“Hear that lonesome whippoorwill
He sounds too blue to fly
That means he’s lost the will to live
I’m so lonesome I could cry”
Honorable Mention: “Where Were You (When The World Stopped Turning)” – Alan Jackson.
Written by Alan. The meaning behind this song pushes it beyond any list. The song is based on the September 11 attacks in 2001. Jackson had finished walking outside and returned indoors to discover news of the attacks on television. He later wrote this heartbreaking song several weeks later.
“Where were you when the world stopped turnin’
That September day?”
I hope you enjoyed this list as much as I enjoyed piecing it together. I know there are MANY artists and songs that a lot of you think should be on this list. I get that. Lists are funny that way.
I’ll go on and admit that I shed a tear a couple times while writing this, especially while listening to some of the Youtube videos I attached.
