1.“He Stopped Loving Her Today,” George Jones (1980)
Country music is first and foremost about one thing – lost love. No song handles that topic better than this one and no singer handles it better than Jones. If space aliens land on earth tomorrow and want to know what country music is, this is the song you play them.
2.“Your Cheatin’ Heart,” Hank Williams (1953)
Difficult to pick the best Hank song of all time, but none was better than this one. Hank lived it, then wrote it, then sang it – this is real life on the air.
3.“Stand by Your Man,” Tammy Wynette (1968)
Colossally popular song still ubiquitous in popular culture today. The political ramifications of the subject matter continue to be debated 40 years later.
4. “Crazy,” Patsy Cline (1961)
This is as silky smooth as the female voice gets.
5.“El Paso,” Marty Robbins (1959)
Never forget, the proper title is “country AND western” music, this is the best Western/cowboy song of them all.
6.“Coal Miner’s Daughter,” Loretta Lynn (1970)
You wouldn’t believe it if it weren’t true; down-home, American roots storytelling at its best.
7.“I Walk the Line,” Johnny Cash (1956)
Simple story of devotion delivered powerfully with the Cash “boom-chicka” instrumentation.
8. “Good Hearted Woman,” Waylong Jennings and Willie Nelson (1976)
Epitomizes the “Outlaw” movement that saved country music and dominated the 70’s. Country has a lot of great duos, but none better than Willie and Waylon.
9. “Hello Darlin’,” Conway Twitty (1970)
Unmistakable spoken word intro jumps out of the radio and Twitty’s heartfelt vocals bring it home.
10. “Mama Tried,” Merle Haggard (1968)
Haggard’s common man poetry about reckless youth, prison and mama – themes that would become seminal to the genre.
11. “The Gambler,” Kenny Rogers (1978)
Every American over 20-years-old has heard the chorus, “you’ve got to know when to hold ‘em, know when to fold ‘em.”
12. “I Will Always Love You,” Dolly Parton (1974)
About every 10 years, someone goes to #1 with a cover of this song, most notably Whitney Houston, but Dolly did it first and best.
13. “Always on My Mind,” Willie Nelson (1982)
How many people ever covered an Elvis song and made it theirs?
14. “I’m so Lonesome I Could Cry,” Hank Williams (1949)
The mournfulness and visual imagery Hank brings home in the lyrics of this song are devastating.
15. “Much Too Young to Feel this Damn Old,” Garth Brooks (1989)
Brooks took country music totally mainstream with other hits, but his most honest, straightforward song is this one – no pyro, no screaming, no wild fiddles, just the story of a modern day cowboy trying to get along.
16. “Lucille,” Kenny Rogers (1977)
This song’s chorus has been parodied so often it’s easy to forget it was once an actual record, and a damn good one.
17. “You Never Even Call Me by My Name,” David Allen Coe (1975)
A nod to country’s silly side may also be its best sing-along ever.
18. “Rhinestone Cowboy,” Glen Campbell (1975)
Forget John Travolta, being cool and having a message and just enjoy it.
19. “Amarillo by Morning,” George Strait (1983)
Still the signature song of country’s most dependable hit-maker for the past 25 years.
20. “D-I-V-O-R-C-E,” Tammy Wynette (1967)
Lyrics so intimate you almost turn the radio down when it comes on, as if you shouldn’t be eavesdropping on the conversation.
21. “Ring of Fire,” Johnny Cash (1963)
Once you’ve heard them, you never forget those horns. If this song were released today, it would sound hip and edgy.
22. “Folsom Prison Blues,” Johnny Cash (1956)
Cash made a career out of being the voice for those who had none and never did it better than he did here.
23. “I Fall to Pieces,” Patsy Cline (1961)
If the idea of some guy dumping Patsy Cline weren’t so unbelievable, this one would probably rank higher.
24. “Country Roads,” John Denver (1971)
West Virginia may have had its statehood revoked to add Puerto Rico if not for the chorus of this tune.
25. “Walking the Floor Over You,” Ernest Tubb (1943)
The first big “Honky Tonk” song set the stage for everything that was to come.
Artistry, importance to the genre and the ability to stand the test of time were the deciding factors
P.S. – Country music is one of my greatest passions. This list is one of my greatest achievements. If you knew the number of people and the amount of man hours and debate that went into creating it (the full list goes all the way to 300), you’re mind would wreck at the enormity. Don’t bother debating this list, it’s right.