Music

10 Best Outlaw Country Songs of All Time

Outlaws break a few laws or at the least ruffle feathers.

Outlaw country artists have been raising hell since the 60s, and it still lives on in a new generation of fiercely independent singers who are keeping the tradition alive. Here are 10 songs that define the genre both past and present.

10.  “Follow Your Arrow” – Kacey Musgraves


Not since Loretta Lynn sang about the pill has a female country artist just flat out spoke her mind. Like her predecessor, Musgraves received little help from radio, as the song only hit No. 42 on the charts. The song, which is about living life on your terms, won the CMA Song of the Year in 2014, making it the lowest charting song ever to receive the award. Musgraves has since established her mark in Nashville by holding true to her Texas roots.

9. “Desperados Waiting for a Train” – Guy Clark

The pain, longing, and nostalgia hit you harder than a train in this slow-chugging melody by a songwriting master. Recorded by The Highwaymen, Jerry Jeff Walker, Rita Coolidge, and others it brings vulnerability to a hard-lived life.

8. “Not Ready To Make Nice” – The Dixie Chicks


Still mad as hell, the Dixie Chicks released this song in June of 2006 as their musical response to the backlash following lead singer Natalie Maines’ criticism of President George W. Bush. The song took home three Grammys, yet mainstream country radio continued to shun the trio.

7. “Copperhead Road” – Steve Earle


This song might rank higher if it weren’t tainted by the recent fad of line dancing to the song’s hard hitting guitar licks. Outlaws don’t line dance to Steve Earle. They close their eyes and let the lyrics stab their soul.

6. “Are You Sure Hank Done It this Way” – Waylon Jennings


You could make an outlaw list and stock it with all Waylon, so it’s hard to narrow down his many hits, but this song from 1975’s Dream My Dreams album was all about Waylon calling BS on Nashville. The lyrics and message hold true today, making it not only iconic, but outright prophetic.

5. “Pancho and Lefty” – Townes Van Zandt


Covered by dozens of artists like Emmylou Harris, Steve Earle, and Merle Haggard and Willie Nelson, who took the song to Number One in 1983, “Pancho and Lefty”, is Townes Van Zandt’s best-known song. Van Zandt never wavered from the outlaw lifestyle and paid the price with his untimely death in 1997. His songwriting influence is evident across many genres of music to this day.

4. “Blue Eyes Crying In the Rain” – Willie Nelson


“Blue Eyes Crying in the Rain” – the highest charting song from Red Headed Stranger and Willie’s first Number One hit – might not fit the profile of outlaw country. But, as part of the famous concept album, the song holds a place of honor in the outlaw genre.

On Red Headed Stranger, Willie stepped out of the constrictions of Nashville and created music his way. “Blue Eyes Crying in the Rain” made people take notice.

3. “The Road Goes on Forever” – Robert Earl Keen


This road anthem is a classic in Keen’s home state of Texas. It was also the title track of the Highwayman’s final album and serves as a direct link from the era of Willie, Waylon, Cash and Kristofferson, to the like-minded alternative country sounds of today.

2. “Good Hearted Woman” — Waylon Jennings and Willie Nelson


Written over a Fort Worth poker game by the Kings of outlaw, this classic was first recorded by Waylon in 1972 before hitting Number One as a duet on Wanted: The Outlaws album in 1976. Tracks off of that album could be used to create this entire list, as it was outlaw country music’s first platinum record.

1.  “Sunday Morning Coming Down” – Johnny Cash


Originally written by Kris Kristofferson and later recorded by Johnny Cash, this melancholic, morning-after tune was the CMA Song of Year in 1970, predating the major outlaw movement of the mid-70s.

When Cash sang the song on his program, The Johnny Cash Show, ABC executives asked him to change the word stoned to home. Despite the pressure of the suits, the Man in Black refused to bend and sang it the way it was written.

If that ain’t outlaw, I don’t know what is.

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10 Best Outlaw Country Songs of All Time