Playlist: 100 Greatest Old Country Songs by the Decade

Trust us when we say that the greatest old country songs still vibe hard today. That’s because these songs (both the story and its tune) remind us of what life truly is – packed in the small moments we often take for granted. When thinking about how simple life is, one that easily comes into mind is the 1964 number one country hit “I Want To Hold Your Hand” by the Beatles. It’s a straightforward song about feeling in love that will make you feel light and giddy. 

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There’s also the 1922 instrumental titled “Sallie Gooden” performed by fiddler Eck Robertson which sounds like something you would play and dance to on a good day. It’s upbeat and full of life. And did you know that this actually stands as the first-ever commercial recording by a country performer?

What makes a country song one of the greatest?

But the question before everything else is: what makes a country song great or the greatest of its time? Well, it’s the story and the twang – the kind of sensation that you can feel down to the tip of your toes. 

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All great old country songs have told stories of love and madness, grief and anger, drunken fun, and quiet solitude that will make you feel like you fit right in as if you’re the hero/ine. And the tunes will sway you to all of these emotions bringing life into the lyrics of the song. These songs became instrumental in the development of the genre and in the rise of others. 

So, we listed here 100 of the greatest country songs from the 1940s until the 2000s that map out the old world of country music.

Hit the Play Button: 100 Greatest Old Country Songs

Take a listen to the top songs of each decade and indulge yourself with some good old country. Maybe, drink a wine too for the full experience. 

The 1940s: “The Hillbilly”

1. New San Antonio Rose by Bob Wills and His Texas Playboys (1940)
2. Walking the Floor Over You by Ernest Tubb (1941)
3. Pistol Packin’ Mama by Bing Crosby and the Andrew Sisters (1944)
4. Smoke on the Water by Red Foley
5. Jole Blon by Harry Choates (1946)
6. Blue Moon of Kentucky by Bill Monroe and The Blue Grass Boys (1947)
7. Smoke! Smoke! Smoke! (That Cigarette) by Tex Williams (1947)
8. Bouquet of Roses by Eddy Arnold (1948)
9. I Saw The Light by Hank Williams (1948)
10. Candy Kisses by George Morgan (1949)
11. Foggy Mountain Breakdown by Flatt and Scruggs (1949)
12. Lost Highway by Hank Williams (1949)
13. Lovesick Blues by Hank Williams (1949)
14. I’m So Lonesome I Could Cry by Hank Williams (1949)
15. Slippin’ Around by Margaret Whiting and Jimmy Wakely (1949)

The 1950s: “The Rise of New Country Style”

1. If You’ve Got the Money, I’ve Got the Time by Lefty Frizzell (1950)
2. The Tennessee Waltz by Patti Page (1950)
3. Why Don’t You Love Me by Hank Williams (1950)
4. It Wasn’t God Who Made Honky Tonk Angels by Kitty Wells (1952)
5. Jambalaya (On the Bayou) by Hank Williams (1952)
6. Kaw-Liga by Hank Williams (1953)
7. There Stands the Glass by Webb Pierce (1953)
8. Folsom Prison Blues by Johnny Cash (1955)
9. Sixteen Tons by Tennesseee Ernie Ford (1955)
10. Crazy Arms by Ray Price (1956)
11. I Walk the Line by Johnny Cash (1956)
12. Walkin’ After Midnight by Patsy Cline (1957)
13. El Paso by Marty Robbins (1959)
14. Heartaches By The Number by Ray Price (1959)
15. White Lightning by George Jones (1959)

The 1960s: “The Bakersfield Sound”

1. I Fall to Pieces by Patsy Cline (1961)
2. She Thinks I Still Care by George Jones (1962)
3. The Back Door (La Porte en Arriere) by D.L. Mernard (1962)
4. Act Naturally by Buck Owens (1963)
5. Ring of Fire by Johnny Cash (1963)
6. King of the Road by Roger Miller (1964)
7. The Race Is On by George Jones (1964)
8. Streets of Baltimore by Bobby Bare (1966)
9. Jackson by Johnny Cash and June Carter (1967)
10. D-I-V-O-R-C-E by Tammy Wynette (1968)
11. Harper Valley P.T.A. by Jeannie C. Riley (1968)
12. Mama Trieeed by Merle haggard and The Strangers (1968)
13. Wichita Lineman by Glen Campbell (1968)
14. Okie from Muskogee by Merle Haggard (1969)
15. Stand By Your Man by Tammy Wynette (1969)

The 1970s: “The Emergence of Outlaw”

1. Angel from Montgomery by John Prine (1971)
2. Coat of Many Colors by Dolly Parton (1971)
3. Kiss an Angel Good Mornin; by Charley Pride (1971)
4. Delta Dawn by Tanya Tucker (1972)
5. Don’t Let the Green Grass Foll You by O.B. McClinton (1972)
6. Old Dogs, Children and Watermelon Wine by Tom T. Hall (1972)
7. The Happiest Girl in the Whole U.S.A. by Donna fargo (1972)
8. Behind Closed Doors by Charlie Rich (1973)
9. Desperados Waiting for a Train by Jerry Jeff Walker (1973)
10. Louisiana Woman, Mississippi Man by Loretta Lynn and Conway Twitty (1973)
11. Convoy by C.W. McCall (1975)
12. Redneck Mother by Ray Wylie Hubbard (1975)
13. She’s Actin’ Single, I’m Drinkin’ Doubles by Gary Stewart (1975)
14. The Pill by Loretta Lynn (1975)
15. Mammas Don’t Let Your Babies Grow Up to Be Cowboys by Waylon Jennings and Willie Nelson (1978)

The 1980s: “Urban Cowboy Movement”

1. He Stopped Loving Her Today by George Jones(1980)
2. Smoky Mountain Rain by Ronnie Milsap (1980)
3. A Country Boy Can Survive by Hank Williams, Jr. (1981)
4. Seven Year Ache by Rosanne Cash (1981)
5. Queen of Hearts by Juice Newton (1981)
6. Always On My Mind by Willie Nelson (1982)
7. Mountain Music by Alabama (1982)
8. Wild and Blue by John Anderson (1982)
9. Old Hippie by Bellamy Brothers (1985)
10. Guitars, Cadillacs by Dwight Yoakam (1986)
11. All My Ex’s Live in Texas by George Strait (1987)
12. Forever and Ever Amen by Randy Travis (1987)
13. If I Had a Boat by Lyle Lovett (1988)
14. Passionate Kisses by Lucinda Williams (1988)
15. The Dance by Garth Brooks (1989)

The 1990s: “The Explosion”

1. Dallas by The Flatlanders (1990)
2. Fancy by Reba McEntire (1990)
3. Friends in Low Places by Garth Brooks (1990)
4. Achy Breaky Heart by Billy Ray Cyrus (1992)
5. Chattahoochee by Alan Jackson (1992)
6. I Was Country When Country Wasn’t Cool by Barbara Mandrell (1994)
7. Independence Day by Martina McBride (1994)
8. Strawberry Wine by Deana Carter (1995)
9. My Maria by Brooks & Dunn (1996)
10. You’ll Never Know by Mindy McCready (1997)
11. Wide Open Spaces by The Chicks (1998)
12. Amazed by Lonestar (1999)
13. Breathe by Faith Hill (1999)
14. Choices by George Jones (1999)
15. Something Like That by Tim McGraw (1999)

The 2000s: “The Big Break of Small-Town Country Artists”

1. I Hope You Dance by Lee Ann Womack (2000)
2. Remember When by Alan Jackson (2003)
3. Songs About Rain by Gary Allan (2003)
4. Redneck Woman by Gretchen Wilson (2004)
5. Save a Horse (Ride a Cowboy) by Big & Rich (2004)
6. Wagon Wheel by Old Crow Medicine Show (2004)
7. Alcohol by Brad Paisley (2005)
8. Before He Cheats by Carrie Underwood (2006)
9. Love Story by Taylor Swift (2008)
10. Welcome to the Future by Brad Paisley (2009)

That’s it, folks! Let us know which of the greatest old country songs were your favorites.