There’s just nothin’ like a good old fashioned honky tonk heartbreaker, and if you follow Whiskey Riff in any capacity, then you know how much all of us here love a good old fashioned, sad country song.
And since some of my favorite artists in the genre right now, like Miranda, have written some of my very favorite sad songs that hurt so good, I wanted to know what some of their favorite’s were that inspired them to write soul-crushing music just like George, Willie, Merle, Waylon and all the other country greats.
She says Guy Clark’s “Desperados Waiting for a Train” was the very first song that ever made her cry as a little girl:
“Sad songs are the best songs when it comes to country music. So many have inspired me.
‘Desperados Waiting for a Train’ by Guy Clark is one of my all time favorite songs.
It’s the first song that ever made me cry as a kid, when I started to understand the story of the song. And ‘Hello in There’ by John Prine, too.”
“Desperados” was written by Guy Clark and originally recorded by Jerry Jeff Walker for his 1973 Viva Terlingua album.
It has been recorded by tons of other artists since then, too, like Rita Coolidge, David Allan Coe, Nanci Griffith and Tom Rush. Guy eventually recorded it for himself in 1975 for his Old No. 1 record.
One of the most famous versions of the song comes from country supergroup The Highwaymen, who released it as the second single from their self-titled album in 1985. Their version peaked at #15 on the U.S. Billboard Hot Country Songs chart later that year.
I knew Miranda would come through with some really solid picks, and she added that the true beauty of both of those songs is the pure and real honesty in every lyric:
“Both of those songs are someone’s real truth and that to me is everything. The imagery on both of those and the conversational aspect draws you in and makes you feel like you are in the story with these characters.
You feel the raw emotion – those two writers were the all time best at that.”
Of course, she’s also fantastic at getting to the root of the human experience and bringing brazen, unabashed honesty to every song she writes, too.
She says the beauty of a sad country song, or any song for that matter, is that it allows us to feel deep emotions we all relate to but maybe don’t wanna own up to out loud:
“Sometimes people are afraid to feel, but music allows us to do that on a deeper level and, because it’s a song, it feels safe to just let that happen.”
Spoken like a true country Queen…
“Desperadoes Waiting For A Train”
And when it comes to picking my favorite sad song of Miranda’s, I could never really choose just one. Depending on the day, I’ll probably give you a different answer, because she has so many good options.
From singles like “Tin Man” and “More Like Her,” to some of her incredible deep cuts like and “Me and Your Cigarettes” and “Carousel,” she knows how to wear her heart on her sleeve and spin it into a soul-crushing tune better than just about anybody in the music business.
But there’s something about her co-write “Vice,” from her 2016 The Weight of These Wings double album, that gets me every single time.
When she said you can really feel it when someone is putting their whole truth into a song, I think this is the perfect example:
“Sting of the needle dropping on a vinyl Neon singer with a jukebox title full of heartbreak Thirty-three, forty-five, seventy-eight When it hurts this good, you gotta play it twice Another vice”
Gonna play this one way more than twice today…
For more of the best sad country songs, check out the Whiskey Riff Sad Country Songs Make Me Happy Playlist: