100 Best Country Songs of All-Time: Part Five (19–1)

We’ve finally arrived at part five! Here are the best of the best. The greatest country songs ever recorded.

19.) “Lost Highway”
Artist: Hank Williams
Writer: Leon Payne
1949

One of the rare Hank recordings that wasn’t written by his own hand, “Lost Highway” nonetheless is a signature and essential Hank song. The lyrics seriously could be tag-line for Hank’s own life.

18.) “Sing Me Back Home”
Artist: Merle Haggard
Writer: Merle Haggard
1967

“Sing Me Back Home” explores familiar themes The Hag often sang and wrote about. Here we see Merle singing about the execution of a death-row inmate and his last request.

17.) “Long Black Veil”
Artist: Lefty Frizzell
Writers: Danny Dill and Marijohn Wilkin
1959

It’s a spooky song with twists and turns, yet the lyrics are straightforward. If you’ve never listened to “Long Black Veil,” I’m not going to give away the verses, but I highly recommend giving this a listen. John Anderson also gives a fantastic and stirring version of the song.

16.) “Dreaming My Dreams With You”
Artist: Waylon Jennings
Writer: Allen Reynolds
1975

Perhaps Waylon’s most vulnerable song. It’s heartbreaking in its subtelty.

15.) “Mama’s Hungry Eyes”
Artist: Merle Haggard
Writer: Merle Haggard
1969

Merle was a master of mixing autobiography and vintage Steinbeck. Much like “Mama Tried,” “Hungry Eyes” contains details from The Hag’s personal life with a little creative license thrown in. It’s also got one of the greatest opening lines to a country song.

14.) “Pancho and Lefty”
Artists: Willie Nelson and Merle Haggard
Writer: Townes van Zandt
1983

Originally recorded by Townes himself in 1972, “Pancho and Lefty” went to number one in 1983 thanks to Willie and Merle. A truly brilliant story-song.

13.) “Whiskey Lullaby”
Artists: Brad Paisley and Allison Krauss
Writers: Bill Anderson and Jon Randall
2004

You’ll struggle to find a more painful, depressing song than this. But that’s what you get when you put an all-time great songwriter with an awesome modern-day hit maker. Paisley and Krauss take this duet to legendary status.

12.) “Amanda”
Artist: Waylon Jennings
Writer: Bob McDill
1974

Waylon proved that outlaw country wasn’t always in your face, four on the floor rock. What helped Waylon stand-out was his ability to slow down that driving back-beat and sing songs that revealed the other side of the outlaw.

11.) “Green, Green Grass of Home”
Artist: Porter Wagoner
Writer: Curly Putman
1965

The listener doesn’t know it, but the first few verses are an inmate’s dream sequence- his last thoughts before his scheduled execution on death row. I got chills just writing that.

10.) “Stand By Your Man”
Artist: Tammy Wynette
Writers: Billy Sherrill and Tammy Wynette
1968

“Stand By Your Man”first became a signature song for Tammy, and it’s now become a signature song for country music.

9.) “El Paso”
Artist: Marty Robbins
Writer: Marty Robbins
1959

Country music has a strong, spiritual connection with the American West. “El Paso” is perhaps the greatest song ever recorded about the West. Vivid images, lyrics that put the listener right in the scene, and a fantastic vocal performance from the great Marty Robbins.

8.) “Together Again”
Artist: Buck Owens
Writer: Buck Owens
1964

Buck was a master of writing the simplest of lyrics yet making them so poignant. Combine that with one of the greatest steel guitar solos in country music history, and you have yourself with an iconic piece of music.

7.) “Hello Darlin’”
Artist: Conway Twitty
Writer: Conway Twitty
1970

Conway Twitty deserves much more recognition for his contributions to country music than he currently receives. Thanks to heart-wrenching songs like “Hello Darlin’,” Conway became one of the most successful artists of the 1970s.

6.) “Walking the Floor Over You”
Artist: Ernest Tubb
Writer: Ernest Tubb
1941

“Walking the Floor Over You” helped electrify country music and took the genre to new frontiers.

5.) “Can the Circle Be Unbroken (By and By)”
Artist: The Carter Family
Composed by A.P. Carter
1935

A,P. Carter composed this recording from the hymn “Will the Circle Be Unbroken.” Recorded countless times from artists as diverse as The Nitty Gritty Dirt Band, Moby, and Johnny Cash, it’s become country music’s theme song.

4.) “Sunday Mornin’ Comin’ Down”
Artist: Johnny Cash
Writer: Kris Kristofferson
1970

Not only did the song help give Kristofferson his break, it entered country music history as a different kind of hit- something that didn’t follow the basic formula of country songwriting. Its downtrodden and out-of-luck point of view can really get the listener sympathizing with the lyrics.

3.) “Mama Tried”
Artist: Merle Haggard
Writer: Merle Haggard
1968

Love for Mama, prison, and trains. Themes that help define not only Merle’s music but the entire genre of country.

2.) “He Stopped Loving Her Today”
Artist: George Jones
Writers: Curly Putman and Bobby Braddock
1980

It helped revive George’s career. The lyrics took unending love to a new level. George called it “morbid” and thought no one would buy the record. Perhaps the greatest vocal performance in country music history, the importance of “He Stopped Loving Her Today” cannot be overstated.

1.) “I’m So Lonesome I Could Cry”
Artist: Hank Williams
Writer: Hank Williams
1949

Straight-forward but poignant. Somber and melancholy. “I’m So Lonesome I Could Cry” is the greatest country song of all-time. Hank took visions of the American South to convey his feelings of loneliness and isolation he was dealing with from his marriage. Hank has been called the “Hillbilly Shakespeare,” and it’s songs like this that exhibit why. The song is elegant yet plain-spoken, as most of the best country songs are. That’s why it’s number one here.

Thanks for reading the list! This was fun to do, and I hope some readers have been exposed to songs they may not have yet heard.