Saddest Country Songs – listed and No. 1 ranked

I don’t want to write this. I’ve been avoiding putting together a list of the saddest country songs for probably 10 years.

I’m happy now, and not looking forward to returning to the places these songs take a person.

I’ve been there. Personally. I’ve plumbed these depths.

Perhaps you have too. In every life, it may be unavoidable.

From a teenager – and I can’t explain why – I was drawn to melancholy. Heartbreak. The saddest country songs resonated with me long before they should have. Long before I experienced for myself the darkness they record.

Long before “my world slipped away,” as Vern Gosdin sang.

But I owe it to myself, to you and to the saddest country songs to write this list as a testament to what country music does best: break our hearts.

This list comes entirely from personal memory. It is my list. Heartache can’t be crowdsourced or measured by algorithm or replicated by artificial intelligence.

Sad Country Music Songs

There are all kinds of sad country music songs.

Sad country music songs about love. Sad country music songs about death. Songs about the loss of loved ones, like Randy Travis’ “I Thought He Walked on Water.” A great sad song about a pet dog, “Feed Jake,” from Pirates of the Mississippi.

There are social justice sad songs like Johnny Cash’s songs “Ira Hayes,” about America’s horrific treatment of its Native people, or “Jacob Green,” about the country’s barbaric mass incarceration system. Mary Chapin Carpenter’s rocking middle finger to the patriarchy: “He Thinks He’ll Keep Her.”

There are even funny sad country songs. George Jones pulled that trick off with “The King is Gone.”

This list of saddest country songs, however, can largely be divided into two categories: love and death, with occasional crossover.

FYI, this list will skew heavily on songs from the 1970s through the 90s because that’s when I was listening most and what I consider to be the genre’s greatest epoch.

So, come with me, if you dare, and read on about the saddest country songs and together, we’ll remember why Doug Stone sang, “they ought to put warning labels on those sad country songs.”

Country Saddest Songs

1. “I’ll Be True to You,” the Oak Ridge Boys (1977)

I haven’t listened to this song in 20 years. It’s too hard. It’s that good. You’re reading this first, but I’m writing this last as I know any productivity I’ll have after listening again will be gone for the day.

Why am I doing this to myself?

This little remembered 3-minutes and 40-seconds is the saddest song in country music history and I will die on that hill.

Just an ordinary story of young kids meeting for a hot love affair, going their separate ways – she stayed true, not him. The years hadn’t been treating her well when they again ran into each other.

“She was on a downhill slide, he was just sliddin’ in.”

“As he looked in to her eyes that night, he never realized, the only real love in his life, was passing by.”

He leaves anyway.

“He heard her calling out to him, and as he walked she cried.

“I’ve been true to you,

“Seems like speaking to me is the least that you can do,” which, for my money, is the single most heartbreaking line in country music history.

Good god.

I won’t spoil the ending if you haven’t heard it. Spoiler alert: it’s not a happy one.

And “I’ll Be True to You” is not cheap. It’s not emotionally obliterating just for the sake of trying to accomplish that. This happened to someone, or pieces of it.

“I’ll be True to You” tops my list of saddest country songs. It’s the only one I’ll be ranking because I’m open to debate about the others, but not this one.

Sad County Songs Love

“As Soon as I Hang Up the Phone,” Conway Twitty and Loretta Lynn (1974)

There are thousands of “breakup” songs in country music, but this is the ONLY one putting the listener – you – in the middle of the breakup as it happens.

Loretta picks up the phone and hears Conway’s voice. She’s relieved as she’s heard rumors he’s looking to end their relationship, but now, hearing his voice, she knows that’s not true. At least, she thinks so.

“No, you don’t understand Loretta, I’m trying to tell ‘ya…” Conway.

“But that’s just it, that’s what I’m trying to tell ‘ya,” Conway says.

“But it is true,” Conway.

“Oh, no,” Loretta.

“Oh, no,” Loretta.

“I’m sorry Loretta, I’m really, really sorry,” Conway.

“I can’t believe you’ll be gone, as soon as I hang up the phone,” Loretta.

“Yeah, I’ll be gone,” Conway.

Genius. How they talk over each other, the phone call sound effects. It’s brilliant.

Genius songwriting, genius singing and, actually, genius voice acting by Conway and Loretta.

“He Stopped Loving Her Today,” George Jones (1980)

This song defines the saddest country song genre. Most lists of sad country music songs start here, and most lists of sad country singers as well. Jones additionally checks in on my list with “The Grand Tour” (1974), “Still Doing Time” (1981) and “Writing on the Wall” (1989).

“I’d Be Better off in a Pine Box,” Doug Stone (1990)

When you break up, and see her again… with someone else.

“I think I’d rather die and go to hell and face the devil.”

True dat.

How far into this list of saddest country songs are we? Seven?

My tears held off that long. You?

Along with George Jones, country music’s other king of misery is Merle Haggard. My favorite is “Looking for a Place to Fall Apart” (1984) with one of my favorite opening lines in country music history: “I’ll probably never see you eye-to-eye again.”

Another major hit of his, “Today, I Started Loving You Again” (1968) and don’t forget “Going Where the Lonely Go” (1982).

For this list of saddest country songs, I tried my best keeping it to singles – stuff that has been played on the radio. Doubtless, some long-forgotten and impossible to find Moe Bandy LP vinyl has tunes that will tear your heart out. Start with “Four Letter Fool.” Merle has a little-known gut wrencher about losing the family farm, “In My Next Life” (1994), worth your time.

“The Hag” will pop up below in “songs of divorce” and “sad country songs death.”

I’m going to stop for a while and come back to this. I might recommend you doing the same.

More Country Songs that are Sad

“As Soon as I Hang Up the Phone” shared the breakup, Kris Kristofferson’s “Come Sundown” (1970), a hit for Bobby Bare, deals with the immediate aftermath. A true poet, Kristofferson mines nuance, “this morning, she’s just leaving me, but come sundown, she’ll be gone,” and grandeur, “I curse the sun for rising.”

Speaking of mornings, try Willie Nelson’s “Last Thing I Needed the First Thing this Morning” (1982) on for size.

For a different type of melancholy, a non-romantic loneliness, nothing tops Kristofferson’s “Sunday Morning Coming Down” made HUGE by Johnny Cash in 1972.

Rodney Crowell co-wrote “Please Remember Me;” Tim McGraw made it a smash in 1999.

“Fifteen Years Ago,” Conway Twitty (1970)

“Lucille,” Kenny Rogers (1977)

“Two Doors Down,” Dwight Yoakam (1993), a song 180-degrees in the other direction of Dolly Parton’s jumper by the same name.

Let’s get Dolly on the list with “Just Someone I Used to Know,” a duet with Porter Waggoner from 1969 that would additionally be recorded by George and Tammy and Emmylou Harris and John Anderson.

Sad Country Songs by Women

Lest you think this list of saddest country songs only features men, let’s hear some sad country songs by women:

“Boulder to Birmingham,” Emmylou Harris (1975)

“I would walk all the way, from Boulder to Birmingham, if I thought I could see, I could see your face.”

Yeah. Me too.

“Soft Place to Fall,” Allison Moorer (1998)

This astonishingly beautiful song appeared on “The Horse Whisperer” soundtrack and was nominated for a Best Original Song Oscar at the 1999 Academy Awards.

“She Thinks His Name Was John,” Reba McEntire (1994)

Reba’s protagonist played it safe her whole life, right down the middle. Until that one-night stand. She thinks his name was John. She knows that’s where she contracted the HIV virus.

A song equal in audacity to Loretta Lynn’s “The Pill” for its frank discussion of issues important to women, issues historically and still overlooked and suppressed by the country music “business” – radio and record labels.

“She’s Got You,” Patsy Cline (1962)

“D-I-V-O-R-C-E,” Tammy Wynette (1968)

Tammy spells out the words she doesn’t want her 4-year-old son to hear, like “C-U-S-T-O-D-Y,” as she goes through a “D-I-V-O-R-C-E,” leading us into our next category of saddest country songs.

Songs of Divorce

True story, researching these songs on YouTube, I began being served marriage counseling ads by the algorithm.

Keeping with the divorce motif, “Yard Sale” from 1992 by Sammy Kershaw.

“Lady just brought ‘em to me, she said she thinks they’ll fit just fine.”

Sammy’s got a yard sale, Dwight Yoakam has a “Home for Sale” in 1993.

“Everything that Glitters is not Gold,” Dan Seals (1986)

Mom chooses her rodeo career over the family, leaving dad to raise their little girl and he’s left to make up excuses for why mom doesn’t come around or call to convince the daughter mom cares at all. A similar theme is explored in Merle Haggard’s “Holding things Together” (1974): “I just signed it love from momma, so that Angie wouldn’t know.”

“Backside of Thirty,” John Conlee (1976). Be sure you catch a version with the edited-out-of-radio third verse.

“I Don’t Call him Daddy,” Doug Supernaw (1993)

“What are We Going to do About Me” (1993) – DANG!, ‘92, ‘93, ‘94 coming STRONG – brings us the third in country music’s Holy Trinity of sorrow: Vern Gosdin.

Sad Country Songs Death

“Chiseled in Stone,” Vern Gosdin (1988)

“Chiseled” was a major single for “the Voice,” earning the Country Music Association “Song of the Year,” but Gosdin could have an entire subcategory on this list.

The “Chiseled in Stone” album additionally featured these tearjerkers: “Do You Believe Me Now,” “Is it Raining at Your House,” and “It’s Not Over Yet,” making it the greatest saddest country songs album of all time.

Another marvelous sad songs album was Willie Nelson’s “Teatro,” featuring Emmylou Harris on backing vocals, which never picked up much popular attention; if you like these kind of songs, you’ll love it.

“Long Black Veil,” Lefty Frizzell (1959)

An amazing story song creating a stark visual endlessly covered by other artists. The opener: “Ten years ago, on a cold dark night, someone was killed ‘neath the town hall light.”

“Red Headed Stranger” was not written by Willie Nelson, but it appeared on his 1974 album of the same name. The “red headed stranger” shoots a woman dead he thought was trying to steal his deceased wife’s horse.

Two more from Merle Haggard: “Kern River” (1985) and “Sing Me Back Home” (1968).

“Green, Green Grass of Home,” Porter Waggoner (1965).

“Don’t Take Your Guns to Town,” Johnny Cash, (1958).

“Evangeline,” The Band and Emmylou Harris (1977).

Country Music Songs About War

A fourth major category of saddest country songs takes war as its subject.

“Travelin’ Soldier” was written by Bruce Robison, a singer-songwriter worth your time, and the Chicks took it to No. 1 in 2002. Young love, small town nostalgia, KIA, hope vanquished, this is a crusher.

Ironically, this song was recorded as George W. Bush was at the onset of sending thousands of U.S. soldiers to war in Afghanistan following 9/11 and starting his campaign of “endless wars” in the Middle East at the behest of oil and business interests, assuring thousands more would be able to identify personally with “Travelin’ Soldier.”

This song was on the charts when Chicks’ lead singer Natalie Maines voiced her disgust with Bush’s pro-war policies on stage, resulting in a backlash from jingoistic country music fans and radio. The song was immediately pulled from “rotation” and the Chicks would never be heard on country radio again.

This action served as the final nail in the coffin for country music radio, after which it became totally unlistenable to, a cultural tragedy which continues to this day.

“50,000 Names on the Wall,” as you might expect, references the Vietnam War Memorial in Washington, D.C. The song was written and recorded by Jamie O’Hara in the ‘90s, George Jones found a little success with it as a single in 2001.

“20-Years Ago,” Kenny Rogers (1987)

Achingly nostalgic. Vividly descriptive. Rogers sings you down the main street of a small town long past its best years as the protagonist recalls better times had at each and every stop on the way than can be experienced there now.

“I guess I should stop by Mr. Johnson’s hardware store.

“His only son was my friend Joe.

“But he joined the Army back in 1964.

“How could we know he would never come back,

“Twenty years ago.”

Songs like this one, “Long Black Veil,” “Sunday Morning Coming Down,” the outdoor settings, walking, the imagery, their haunting, chilling quality make you want to reach for a jacket. This one too, if it wasn’t so damn hot and muggy:

“Galveston,” Glen Campbell, 1969.

There it is. My definitive list of saddest country songs.

Don’t send me your Kleenex bill, and if you have one you think I overlooked, drop it in the comments.