100 Best Country Songs of All-Time: Part Three (59–40)

And here we have part three!

59.) “Streets of Bakersfield”
Artists: Buck Owens and Dwight Yoakam
Writer: Homer Joy
1973 (Owens’ Solo) and 1988 (Yoakam and Owens)

Originally a solo record from Owens, “Streets of Bakersfield” reached a whole new level when the two California country icons teamed up.

58.) “To Beat the Devil”
Artist: Kris Kristofferson
Writer: Kris Kristofferson

Part narration, part life lesson in song. “To Beat the Devil” is one of the most perfectly written songs of all-time, from the best songwriter the world has ever seen. Although, it’s about a struggling musician who wants his message to be heard, everyone can take something from the lyrics. The final verse just begs to be shouted triumphantly.

57.) “Midnight in Montgomery”
Artist: Alan Jackson 
Writers: Alan Jackson and Don Sampson

An eerie, eerie song. Many artists have tried to pay tribute to Hank Sr., and while the efforts are noble, many fail to do the legendary artist justice. “Midnight in Montgomery” is almost the perfect tribute.

56.) “All My Rowdy Friends (Have Settled Down)”
Artist: Hank Williams Jr.
Writer: Hank Williams Jr.

The stuff associated with Hank Jr., can sometimes overshadow his music. And it’s a shame. He’s a hell of a songwriter, with a knack for taking varying life experiences and putting them to song.

55.) “High Cost of Living”
Artist: Jamey Johnson
Writers: Jamey Johnson and James T. Slater

There are fair amount of Jamey Johnson songs that could warrant mention on this list. He’s one of the greatest modern songwriters, and “High Cost of Living” is the perfect microcosm for what Jamey’s music is made of.

54.) “Copperhead Road”
Artist: Steve Earle
Writer: Steve Earle

Copperhead Road is a revolutionary album in country music, providing the inspiration and sound for countless artists who blend country and rock. The title track is a fantastic piece of work, tracing a moonshining family’s legacy while referencing politics and life in the mountains. It would foreshadow the direction Earle’s career would take.

53.) “Take this Job and Shove It”
Artist: Johnny Paycheck
Writer: David Allan Coe

Songs like this are what country music is built upon.

52.) “Lonesome, On’ry and Mean”
Artist: Waylon Jennings
Writer: Steve Young

Waylon was going through hell before recording this record. He had been suffering from hepatitis and found his creativity stifled by his record label. Enter Neil Reshen. Reshen helped Waylon negotiate a new contract, allowing Waylon to record the music and sound he wanted. Many songs have been put forth as the theme of the outlaw movement, but I’d say “Lonesome, On’ry and Mean” is the definition of Waylon’s sound.

51.) “Blue Eyes Crying in the Rain”
Artist: Willie Nelson
Writer: Fred Rose

A country standard, “Blue Eyes Crying in the Rain” is a mournful piece of music. Side-note, it’s also my mom’s favorite Willie Nelson record.

50.) “Harper Valley PTA”
Artist: Jeannie C. Riley
Writer: Tom T. Hall

Talk about creating a stir! Artists, especially women artists, were not expected to record songs like this in 1960s Nashville. It’s a truly iconic song in the history of the genre.

49.) “If Drinkin’ Don’t Kill Me (Her Memory Will)”
Artist: George Jones
Writers: Harlan Sanders and Rick Beresford

Another song from George that could’ve been taken out of his own life-story. George frequently replaced the “her” in the lyrics with “Tammy,” in reference to Tammy Wynette, the legendary artist who was also once married to George.

48.) “Family Tradition”
Artist: Hank Williams Jr.
Writer: Hank Williams Jr.

Hank Jr., was fed up with being expected to just release and play music that was an imitation of his father. “Family Tradition” was a big middle finger to those that were disappointed in Hank’s own unique sound.

47.) “Backside of Thirty”
Artist: John Conlee
Writer: John Conlee

“Backside of Thirty” contains perhaps one of the best-written first verses to a song.

46.) “Me and Bobby McGee”
Artist: Roger Miller
Writers: Kris Kristofferson and Fred Foster

Roger Miller was a huge help to the outlaw movement in country music. He palled around with Waylon, Willie, and Kris, and could frequently found at Tootsie’s and Sue Brewer’s Boar’s Nest. “Me and Bobby McGee” is strongly associated with Janis Joplin, but it was Roger Miller who first had a hit on it.

45.) “Guitars, Cadillacs”
Artist: Dwight Yoakam
Writer: Dwight Yoakam

This is the Dwight Yoakam sound.

44.) “Are You Sure Hank Done It This Way”
Artist: Waylon Jennings
Writer: Waylon Jennings

The driving back-beat, the steel guitar. And that’s just how the music sounded. The lyrics are fantastic as Waylon gives an sardonic look at those who were pushing country away from its roots.

43.) “I’m Moving On”
Artist: Hank Snow
Writer: Hank Snow

The most underrated artist in country music history? Hank Snow has to be in the discussion. “I’m Moving On” has become a defining country music record.

42.) “I’m Not Lisa”
Artist: Jessi Colter
Writer: Jessi Colter

Jessi Colter wrote and recorded this song about being in a relationship with someone who can’t get over his ex and still calls her name.

41.) “Instant Coffee Blues”
Artist: Guy Clark
Writer: Guy Clark

Everyone has their own interpretation of this song. I’ll leave it to you to decide what it means.

40.) “After the Fire is Gone”
Artists: Conway Twitty and Loretta Lynn
Writer: L.E. White

One of the greatest duets in country music history. “After the Fire is Gone” is a brilliant portrait of two lovers who find solace in each other when the love at home is burnt out.

Coming Next Time: 39–20