Top Progressive Country Songs
Rank All Time Artist Song Subgenre(s) Other Genre(s) Year
1
1409
 Townes Van Zandt Pancho and Lefty Singer/Songwriter 1972
2
1575
 Willie Nelson Blue Eyes Crying in the Rain Outlaw Country 1975
3
3502
 The Charlie Daniels Band The Devil Went Down to Georgia Progressive Bluegrass Country Rock 1979
4
4073
 Kris Kristofferson Sunday Mornin' Coming Down Singer/Songwriter 1970
5
4850
 Johnny Cash Cocaine Blues Outlaw Country Rockabilly 1968
6
5271
 Waylon Jennings Are You Sure Hank Done It This Way Outlaw Country 1975
7
5299
 Johnny Cash Wanted Man Outlaw Country 1969
8
6020
 Waylon Jennings Luckenbach, Texas (Back to the Basics of Love) Outlaw Country 1977
9
6088
 Kris Kristofferson Me & Bobby McGee Singer/Songwriter 1970
10
6240
 Kris Kristofferson Help Me Make It Through the Night Singer/Songwriter 1970
11
6242
 Waylon Jennings Good Hearted Woman Outlaw Country 1971
12
6311
 Waylon Jennings and Willie Nelson Mammas Don't Let Your Babies Grow Up to Be Cowboys Outlaw Country 1978
13
7194
 Johnny Paycheck Take This Job and Shove It Outlaw Country 1977
14
7306
 Tom T. Hall The Year That Clayton Delaney Died Singer/Songwriter 1971
15
9078
 Willie Nelson Whiskey River Outlaw Country 1978
16
9429
 Sturgill Simpson Turtles All the Way Down Outlaw Country 2014
17
9488
 Guy Clark L.A. Freeway Outlaw Country Singer/Songwriter 1975
18
9575
 Guy Clark Desperados Waiting for a Train Outlaw Country Singer/Songwriter 1975
19
9815
 Hank Williams, Jr. Family Tradition Outlaw Country 1979
20
9874
 Joe Ely Honky Tonk Masquerade Outlaw Country 1978

Songs "bubbling under" the all-time top 10000:
The Highwomen Highwomen Outlaw Country Contemporary Country 2019
Johnny Cash 25 Minutes to Go Outlaw Country 1965
Billy Joe Shaver I Been to Georgia on a Fast Train Outlaw Country 1973
Johnny Cash Sunday Morning Coming Down Outlaw Country 1970
Waylon Jennings Amanda Outlaw Country 1979
Waylon Jennings Dreaming My Dreams with You Outlaw Country 1975
Jerry Jeff Walker Up Against the Wall You Redneck Mother Outlaw Country 1973
Mickey Newbury An American Trilogy 1971
Joe Ely Boxcars Outlaw Country 1978
Willie Nelson Me and Paul Outlaw Country 1971
Dillard & Clark Polly Country Rock 1969
Jamey Johnson High Cost of Living Outlaw Country 2008
Johnny Cash San Quentin Outlaw Country 1969