Sad Country Songs Make Me Happy – Ben Burgess’ Pick: “Ruby, Don’t Take Your Love To Town” By Kenny Rogers

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Ben Burgess knows how to write a damn sad country song.

And if you follow Whiskey Riff in any capacity, then you know how much all of us here absolutely love them.

Since some of my favorite artists in the genre right now 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.

So far for this Sad Country Songs series, we’ve heard some great picks from Whiskey Myers frontman Cody Cannon, Wade Bowen, Hailey Whitters, Miranda Lambert, Graycie York, Riley Green, Randall King, Parker McCollum, Ashland Craft, Carly Pearce, Charles Wesley Godwin, Ernest, and today, Ben is giving us a great recommendation with his pick.

He says his all-time favorite is Kenny Rogers’ version of “Ruby, Don’t Take Your Love To Town,” which was a song his dad used to love:

“My favorite sad country song is one of my old man’s favorites, ‘Ruby’ by Kenny Fuck*n’ Rogers. A tale of an old war vet and his two-timing woman.

It’s got an upbeat feel with the saddest fuck*n’ lyrics over it, and that, y’all, is the meat and potatoes for a sad country song.”

Written by Mel Tillis, the song was first recorded by Waylon Jennings in 1966, with Kenny releasing his version in 1969, and tells the story of a paralyzed veteran watching his wife get all dolled up to go out without him.

He believes she’s going out to see a new guy, and it tears him up inside, so much so that he wishes he could move and “get my gun and put her in the ground.”

Yeah, it’s pretty intense, and Ben says it’s one he listened to often growing up in Texas, and is now a go-to when he’s drinking:

“I listened to this growin’ up and I jam it every time I get drunk.

The writer of the song, Mel Tillis, wrote the tune about his neighbor who was a war vet.”

He added that these kinds of songs always make him feel a little less alone:

“Who don’t wanna hear about a guy who’s got it worse off than you? It always helps me see the bright side no matter how dark it is.”

Touché, Mr. Burgess…

And when it comes to his own writing, Ben says he just wants to speak the truth, even if it’s less than pleasant:

“Sad country songs are the truth… and that’s what I try to write.

Sometimes that truth is so ugly you have to put some nice melodies, sad words, and a sick beat on it to help the world catch the vibe.”

If you’re as into sad country songs that all but rip your heart out of your chest as I am, this one’s for you…

“Ruby, Don’t Take Your Love To Town”

And when it comes to picking my favorite sad country song of Ben’s, I’d have to go with “White Picket Fence,” from his 2022 debut studio album Tears the Size of Texas.

He comes to terms with the end of a relationship and the dream of a perfect “white picket fence” life with a girl he really loved, and not because anything catastrophic happened between them… it just felt wrong deep down in his heart for whatever reason.

It has that sort of melancholy production he mentioned in that you might not immediately realize how sad it is, but if you really dive into the lyrics, it’s a heartbreaker that is fantastically well-written and I’d highly recommend you checking out.

“White Picket Fence”

And if you really wanna get in your feels today, make sure you check out our Sad Country Songs Make Me Happy playlist.

Listen to the playlist on Spotify.

Listen on Apple Music.

A beer bottle on a dock



A beer bottle on a dock