Top 10 Outlaw Country Songs

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The ’50s and ’60s saw an excess of rhinestone-clad suits and perfectly satiated hair, as country’s biggest stars still did a quaint double-step while singing about love and heartache.

While this golden age certainly produced a number of indisputable hits, it was the country artists who openly defied genre conventions, grew their hair to their shoulders and embraced the lifestyle of a rock ‘n’ roller who are the direct ancestors of country today – we’re talking Outlaw Country.

Artists like Willie Nelson, Waylon Jennings and Merle Haggard changed country music forever when they decided to take control of their art and shed the pervasive Nashville sound. Focusing on self-reflection, wry humor and desperate lifestyles, the subgenre was the provocative younger brother of the glitzy country Opry the world had become comfortable with.

Below, we go over 10 of the most important outlaw movement songs that shook things up and raised a little hell. Let’s dive below.

1. “Mom Tried” (Merle Haggard)

In “Mama Tried”, Haggard struggles with the pain he caused his own mother by being incarcerated in San Quentin in 1957. Haggard eventually served three years for robbery.

Haggard discussed the song with the American songwriter before his death, saying, “When I was 20, I was in San Quentin. ‘Mama Tried’ is probably a child of all of this. The song says that I am “the only and old rebellious child”. I had two older siblings, but they were excellent citizens, they never went to jail. I was the one and only rebel.

He continued, “The first time I ran away from home I was 11. I wasn’t running from a bad home, I was running towards an adventure.”

It’s classic outlaw material and proof that Haggard didn’t just “talk the talk”.

2. “Country boy with long hair” (Charlie Daniels)

Charlie Daniels had an interesting relationship with “Long-Haired Country Boy”. The song opens with the lyrics ‘Cause I get high in the morning / And get drunk in the afternoon. While the line may seem to be the height of the course when it comes to outlaw country, Daniels always felt the line clashed with his religious beliefs. “It’s such a big drug and alcohol problem with kids, and it went against my Christian feelings to do anything that anyone might interpret as promoting that lifestyle, or of those things, alcohol and drugs,” he once said.

Although not always championed by Daniels, the song has become one of the movement’s most iconic tracks. In addition to addressing drug use, the song also takes aim at the long-held belief that rock n’ roll (and by affiliation outlaw country) is “devil’s music”. He is confident and stubborn, perfect for an outlaw.

3. “Whiskey River” (Willie Nelson)

Like his ubiquitous hits “Always On My Mind” and “Blue Eyes Crying In The Rain,” “Whiskey River” isn’t a Willie original, but we’ll be damned if it’s not the most memorable release.

The song was originally recorded by one of Nelson’s close friends and fellow Texan, Johnny Bush. Although the song found some success as Bush, it reached new heights when Nelson recorded it a year later for his album. Willie Rifle.

Nelson memorably sang the tune to drown your sorrows in alcohol in the pilot episode of Live from the Austin city limits. The red-haired Stranger deftly plucked the guitar line while singing Whiskey River takes my mind / Don’t let his memory torture me.

4. “I’m the only hell (never raised mom)” (Johnny Paycheck)

Johnny Paycheck isn’t looking for trouble in “The Only Hell (Mama Ever Raised),” though it looks like he can’t walk away from it for too long.

From the very first lines, he tells the listener that it wasn’t his own kleptomania that drove him to steal a car, it was just that his mom missed loving him a bit: Guess that’s why she let me go so far /
Mom tried to stop me from stealing / Guess that’s why I had to steal that car.

Later, he arrives in Atlanta, a bit short of money. He just had to get downtown, you see, so he served a quick fix: These neon lights were calling me and somehow I just had to get downtown / So I reached the glove box, another liquor store fell.

5. “Cocaine Blues” (Johnny Cash)

“Cocaine Blues” reworks the Appalachian standard “Little Sadie,” adding an intense moral riddle and a little white flash. Although it has been performed many times by a number of musicians, no one has played it quite like Johnny Cash did for the inmates of Folsom Prison.

In the song, Cash tells the story of Willie Lee, who tried to outrun the cops on cocaine after killing a woman. Along with Cash’s own struggles with drugs, he infuses just enough truth into the song that you’d think The Man In Black himself might be on the loose. Of course, he was just playing the part, “Cocaine Blues” remains a classic in outlaw mythos.

6. “Don’t you think that bit of outlaw got out of control” (Waylon Jennings)

A big part of what makes Waylon Jennings one of the best outlaw artists is his ability to be honest and authentic about life – the good, the bad, and the ugly.

In “Don’t You Think That Bit Of Outlaw Got Out Of Control”, Jennings looks back on a time when the DEA raided his hotel room for cocaine. Although he acted quickly and flushed all the remains down the toilet, he was still arrested for possession and means of distribution.

In the song, Waylon struggles with the audience’s inability to differentiate between his outlaw stage persona and the man he was in everyday life. Although he took a step back from all things outlaw later in his career, he remains one of the main stewards of the movement.

7. “Family Tradition” (Hank Williams Jr.)

Hank Williams Jr.’s life changed forever when a rock climbing accident nearly took his life in 1975. Although he toyed with a new musical direction before the fall, he then took a sharp turn towards cutting-edge rock sound.

The change was not welcomed with open arms by many of his fans. During his concerts, masses of spectators would come out after he refused to play his father’s music. At times the crowd dwindled to a measly 200, but Bocephus played his entire set, unfazed.

The change eventually found its way into his recording sessions. Producer Jimmy Bowen met Williams Jr. at a recording studio in Muscle Shoals, Alabama halfway through a new album project. “Nobody wants to hear what I write,” Williams Jr. told him. Bowen replied, “Well, they’re gonna have to because I didn’t bring any songs with me.” The singer then took him aside and played “Family Tradition.” “It’ll do it,” Bowen noted.

The song evokes the difficult lifestyle that he and his father experienced. It’s the purest outlaw mentality: do things your way, regardless of the consequences.

8. “High cost of living” (Jamey Johnson)

Although the outlaw movement is generally considered to be confined to the 70s, the same spirit can be found in the genre in more contemporary contexts. A notable example of this is Jamey Johnson’s “high cost of living”.

With lyrics like, as soon as Jesus turned his back / I had found my way across the track / I was just looking to score another deal / With my back against that damn eight ballJohnson tackles the same themes as his predecessors, keeping the outlaw pathos alive, but with a more insightful sensibility.

9. “I don’t live long like this” (Waylon Jennings)

Although many outlaw country songs only vaguely reference characters from the wild west, “Ain’t Living Long Like This” could be the theme song for Jesse James or Billy the Kid.

He sings, I looked for trouble and found it son / Straight through the barrel of a lawman’s gun… You know the story of how the wheel turns? / Don’t let them take you to the man downtown. Truly about being against the law, “Ain’t Living Long Like This” takes the outlaw pastiche home.

10. “Moms don’t let your babies be cowboys” (Waylon Jennings and Willie Nelson)

There’s no more quintessential outlaw country than this track. The lyrics paint an astute portrait of the kind of person that colors the outlaw movement: Those who don’t know him won’t like him and sometimes they won’t know how to take him / He’s not wrong, he’s just different but his pride won’t let him do things to make you think he’s right.

Although the song was originally recorded by Ed Bruce and co-written with his wife Patsy Bruce, the version that topped the charts came from the notorious duo of Nelson and Jennings. With their track record, the song becomes a cautionary tale against… well, themselves. Two outlaw cowboys with their fair share of faded old levis and Lonestar Belt Buckles sing about their own tendencies to be a little fickle and a little misunderstood.

(Photo by Jim Bennett/WireImage)

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