The 20 Best Outlaw Country Songs of All Time

Outlaw country was a subgenre that thrived in the mid to late 1970s. It was a reaction against the Nashville Sound backed by Music Row executives at the head of the country establishment.

As such, outlaw country musicians disregarded profit-maximizing rules and restrictions, spurred on by the counter-culture sentiments that were so common in those times.

That said, the subgenre died down in the 1980s for various reasons. First, outlaw country musicians had grown out of it. Second, the Nashville sound had been replaced by country pop.

Third, commercialization had overtaken outlaw country in much the same way commercialization had overtaken its mainstream counterpart. Outlaw country has successors. However, they are their own thing rather than mere imitations, which is as it should be.

Here is our opinion of the 20 best outlaw country songs ever released:

20. “Don’t You Think This Outlaw Bit’s Done Got Out of Hand?” – Waylon Jennings

This song is sometimes seen as a meditation on the movement. Whatever the truth, it is known that Waylon Jennings took inspiration for the lyrics from his drug habit. As the story goes, he was arrested in 1977, though he was released because he managed to flush his cocaine while the police were distracted.

19. “London Homesick Blues” – Jerry Jeff Walker

The exact situation laid out in “London Homesick Blues” won’t land perfectly with every listener. After all, most people have never been a Texan feeling out of place in London. Still, the general sentiment of homesickness should be familiar to a wide range of people, thus making this song easy to relate to.

18. “The Fightin’ Side of Me” – Merle Haggard

This song might be a bit of a controversial pick. It isn’t just patriotic. One can make a decent case that it crosses the line of being downright jingoistic.

Despite this, this song does have a belligerent spirit, which fits well with outlaw country music as a whole. Going up against an establishment isn’t easy. Outlaw country musicians were quite willing to fight for what they believed in, even if that wasn’t true in a physical sense.

17. “Folsom Prison Blues” – Johnny Cash

“Folsom Prison Blues” comes from Johnny Cash’s early career. Specifically, it was one of the songs on his debut studio album. Over time, “Folsom Prison Blues” became more and more prominent, not least because Cash liked to use it to open his concerts.

Strictly speaking, this song is an example of outlaw country music. Its initial release in 1955 predates the movement by a considerable margin. Even so, it has earned a spot on the list because it resonates so strongly with the movement’s ethos.

16. “Blood Red and Going Down” – Tanya Tucker

Tanya Tucker became a music sensation as a teenager. It seems safe to say that she was under enormous pressure to replicate her initial success.

However, Tucker more than managed to meet those expectations with her second studio album, What’s Your Mama’s Name. It had not one but two songs that managed to reach the top of the country chart. “Blood Red and Going Down” was the second of those two hits.

15. “Copperhead Road” – Steve Earle

“Copperhead Road” was Steve Earle’s most successful song when it came out in 1988. The song tells the story of a Vietnam War veteran named John Lee Pettimore III, whose grandfather and father were bootleggers.

He has no interest in the same business, which makes sense because the end of Prohibition brought about a notable decrease in bootlegging. Instead, he plans to grow marijuana. Moreover, he intends to use the lessons he learned during his service to help him conceal his activities.

14. “Pancho and Lefty” – Townes Van Zandt

Interested individuals might recognize “Pancho and Lefty” because of the cover by Willie Nelson and Merle Haggard. Even so, Townes Van Zandt was the one who sang the original.

Some people might wonder whether the song took inspiration from the life of the Mexican general Pancho Villa. If so, Van Zandt himself wasn’t sure. The song’s details don’t match up with what happened in real life, but that isn’t much of an obstacle because songs aren’t necessarily historically accurate any more than other art forms.

13. “Whiskey River” – Willie Nelson

Breakup songs are country staples. The viewpoint character in “Whiskey River” has taken his breakup very poorly, which is why he is doing his best to drown his memories through copious amounts of alcohol. It has a spot on this list because it is one of the best examples of a breakup song, no small achievement considering the sheer number of them that exist.

12. “Long-Haired Country Boy” – Charlie Daniels

A refusal to fall in line with general expectations is one of the core sentiments behind counter-culture movements. As a result, Charlie Daniels’s “Long-Haired Country Boy” is very much in line with the spirit of outlaw country music.

He doesn’t care what other people do. However, he is content to laze around getting drunk and stoned rather than pursue the markers of success by conventional standards.

11. “Family Tradition” – Hank Williams, Jr.

“Family Tradition” can be considered Hank Williams, Jr.’s statement of self-affirmation. For those unfamiliar, he is the son of the country legend Hank Williams.

Unsurprisingly, he struggled to step out of his father’s shadow when he embarked on a music career. Over time, Hank Williams, Jr. managed to find an independent style rather than remain a poor copy forever, which seems to have been spurred on by a near-fatal fall in 1975. This song was a declaration of his intent to challenge the country music establishment.

10. “Georgia On a Fast Train” – Billy Joe Shaver

Some people might know this song as “I Been to Georgia On a Fast Train” because that was the original name when it came out in 1973. It made quite an impression in those times, meaning it played an important role in catapulting Billy Joe Shaver onto his path of success. Later, the song was re-released as “Georgia On a Fast Train” in 1994, though it made less of an impression that time around.

9. “Highwayman” – The Highwaymen

The Highwaymen refers to a collection of four country greats who existed at the core of outlaw country music. Johnny Cash was one of them. Similarly, Waylon Jennings was another.

The remaining two were Kris Kristofferson and Willie Nelson. Funny enough, the Highwaymen were active for quite a while after outlaw country music had faded from prominence, as shown by how they released their last studio album in 1995.

Even so, “Highwayman” counts as one of the finest songs to ever come from the movement, though it came out a bit later than most of its counterparts.

8. “I’m Not Lisa” – Jessi Colter

Romantic relationships can run into a wide range of potential complications. Given the song’s name, chances are good that interested individuals can guess “I’m Not Lisa” is about a romantic relationship in which the significant other hasn’t gotten over his last lover.

Something that put the viewpoint character in a very awkward and very frustrating position. It was far from being Jessi Colter’s first song, but it was her first real hit as a solo artist.

7. “Sunday Mornin’ Comin’ Down” – Kris Kristofferson

Ray Stevens was the first one to record this song. His version did well enough, as shown by how it reached the number 55 position on the country chart. Instead, it was Johnny Cash’s cover that soared to the top of the same chart, thus making it a household name.

Despite these things, “Sunday Mornin’ Comin’ Down” is associated with Kris Kristofferson because he was the songwriter. To be exact, this was the song that made his music career. As Kristofferson put it, it was admired by many of the people he admired, which must have been a remarkable feeling.

6. “I’m the Only Hell (Mama Ever Raised)” – Johnny Paycheck

Johnny Paycheck was another country musician who rose to prominence in this era. Unfortunately, his career ran into serious issues, meaning he isn’t remembered as well as some of his counterparts.

Regardless, “I’m the Only Hell (Mama Ever Raised)” is another song embodying the spirit of outlaw country music. It is similar to Merle Haggard’s “Mama Tried” in many respects, but it is more than capable of standing on its own.

5. “Are You Sure Hank Done It This Way” – Waylon Jennings

Hank Williams was a major source of inspiration to outlaw country musicians. As such, it makes sense that the latter would use his name to make their views known to listeners. “Are You Sure Hank Done It This Way” served two purposes.

One, it gave praise to Hank Williams. Two, it criticized the Music Row executives responsible for the conditions the outlaw country musicians loathed. These two things synergized well because the first was turned into a metaphorical club for the latter.

4. “Take This Job and Shove It” – Johnny Paycheck

Some people have jobs they enjoy. Sadly, that is far from being guaranteed, meaning work is a common source of complaints. For that matter, even if people enjoy their jobs for the most part, it is still very much possible for them to become frustrated from time to time.

Thanks to these things, it is easy to sympathize with the sentiments behind “Take This Job and Shove It.” That extends to the part in which the viewpoint character makes it clear that he is thinking about quitting rather than truly quitting. After all, everyone needs to eat somehow, meaning they can’t always follow through with momentary whims.

3. “The Red-Headed Stranger” – Willie Nelson

“The Red-Headed Stranger” isn’t necessarily Willie Nelson’s best or best-known song. Instead, it matters because it is the title track of the studio album of the same name.

In turn, that is relevant because The Red-Headed Stranger is when Nelson took creative control over his musical output. Something central to the outlaw country musicians’ hostility towards the country music establishment.

2. “Mama Tried” – Merle Haggard

“Mama Tried” was the most important song on the studio album of the same name. It was the title track. Moreover, “Mama Tried” was the first single, meaning it paved the way for its album-mates in the public consciousness.

Strictly speaking, the song isn’t autobiographical. Merle Haggard was never sentenced to life imprisonment without parole. Otherwise, he wouldn’t have been able to embark on his music career.

Despite that, the song drew a great deal from his experiences because he did serve time in prison for a series of crimes.

1. “Man in Black” – Johnny Cash

Johnny Cash’s career started long before outlaw country music got off the ground. He embarked on his music career in the mid-1950s, which was approximately two decades before the movement’s height.

Despite these things, Johnny Cash is widely acknowledged as one of the central figures of outlaw country music. “Man in Black” is one of his most iconic songs. It is representative of him as an artist because that was his nickname.

Moreover, “Man in Black” was a protest at the poor treatment of those less well-off, meaning it was very much tuned into the counter-culture sentiments of the 1970s.

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