The ’50s and ’60s saw an excess of rhinestone-clad suits and perfectly quaffed hair, as the biggest country stars were still doing a quaint one-two-step while crooning about love and heartache.

While that golden era certainly produced a number of indisputable hits, it was the country artists that openly defied the conventions of the genre, grew their hair down to their shoulders, and adopted the lifestyle of a rock n’ roller that 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 artistry and shed the ubiquitous Nashville sound. Focusing on self-reflection, wry humor, and desperado lifestyles, the sub-genre was the defiant younger brother of the glitzy Opry country the world had become comfortable with.

Below we’re going through 10 of the most prominent songs from the outlaw movement that shook things up and raised a little hell. Let’s dive in below.

1. “Mama Tried” (Merle Haggard)

In “Mama Tried” Haggard wrestles with the pain he caused his own mother by being incarcerated at San Quentin in 1957. Haggard ultimately served three years on a robbery conviction.

Haggard chatted about the song with American Songwriter before his death, saying, “By the time I was 20 years old, I was in San Quentin. ‘Mama Tried’ is probably a child of all that. The song says I’m the ‘one and old rebel child.’ I did have two older siblings, but they were excellent citizens, never went to jail.  I was the one and only rebel.”

He continued, “First time I ran away from home I was 11. I wasn’t running away 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. “Long-Haired Country Boy” (Charlie Daniels)

Charlie Daniels had an interesting relationship with “Long-Haired Country Boy.” The song opens up with the lyrics ‘Cause I get stoned in the morning / And get drunk in the afternoon. Though the line might seem to be par for the course when it comes to outlaw country, Daniels always felt the line clashed with his religious beliefs. “It’s such a big problem with drugs and alcohol with kids, and it just went against my Christian feelings to actually do anything that somebody could construe with being promoting that lifestyle, or those things, the alcohol and drugs,” he once said.

Despite not always being championed by Daniels, the song has gone down as one of the movement’s most iconic tracks. In addition to touching on drug use, the song also takes aim at the long-held belief that rock n’ roll (and by affiliation outlaw country) is “the devil’s music.” It’s self-assured and obstinate —perfect for an outlaw.

3. “Whiskey River” (Willie Nelson)

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

The song was originally recorded by one of Nelson’s close friends and fellow Texan, Johnny Bush. Though the song found some success under Bush’s name, it soared to new heights when Nelson recorded it a year later for his album Shotgun Willie.

Nelson memorably sang the tune about drowning your sorrows in booze on the pilot episode of Live From Austin City Limits. The Red-Headed Stranger expertly plucked the guitar line while singing Whiskey River take my mind / Don’t let her memory torture me.

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

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

From the opening lines, he tells the listener that it’s not his own kleptomania that caused him to steal a car, it’s just that his mama was a little short on loving him: I guess that’s why she let me go so far /
Mama tried to stop me short of stealing / I guess that’s why I had to steal that car.

Later he rolls into Atlanta, a little strapped for cash. He just had to get downtown you see so he served a quick fix: Those neon lights was calling me and somehow I just had to get downtown / So I reached into the glove box, another liquor store went down.

5. “Cocaine Blues” (Johnny Cash)

“Cocaine Blues” reworks the Appalachian standard “Little Sadie,” adding in an intense moral conundrum and a little white lightning. Though it has been performed many a time by a number of musicians, no one played it quite the way Johnny Cash did for the inmates at Folsom Prison.

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

6. “Don’t You Think This Outlaw Bit’s Done Got Out of Hand” (Waylon Jennings)

A large 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 This Outlaw Bit’s Done Got Out of Hand,” Jennings reflects on a moment when the DEA raided his hotel room in search of cocaine. Though he acted quick and flushed any remnants down the toilet, he was still arrested for possession and means to distribute.

In the song, Waylon struggles with the public’s inability to differentiate his outlaw stage persona and the man he was in everyday life. Despite, taking a step back from the whole outlaw thing later on in his career, he still remains one of the movement’s primary stewards.

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

Hank Williams Jr.’s life was forever changed when a climbing accident nearly claimed his life in 1975. Though he toyed around with a new musical direction prior to the fall, he took a hard turn into a rock-edged sound afterward.

The change wasn’t welcomed with open arms by many of his fans. During his live shows, masses of concertgoers would walk out after he refused to play his father’s music. Sometimes the crowd would dwindle down to a measly 200 attendees, yet Bocephus played his entire set, unfazed.

The shift eventually found its way into his recording sessions as well. Producer Jimmy Bowen met Williams Jr. at a Muscle Shoals, Alabama recording studio midway 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 pulled him aside and played “Family Tradition.” “That’ll do it,” Bowen noted.

The song touches on the hard-living lifestyle both he and his father experienced. It’s the outlaw mentality as its purest—doing things his way, no matter the consequences.

8. “High Cost of Living” (Jamey Johnson)

Though the outlaw movement is generally thought of as being confined to the ’70s, the same spirit can be found in the genre in more contemporary settings. One notable example of this is Jamey Johnson’s “High Cost of Living.”

With lyrics like, as soon as Jesus turned his back / I’d found my way across the track / Lookin’ just to score another deal / With my back against that damn eight ball, Johnson touches on the same themes as his predecessors, keeping the outlaw pathos alive, albeit with a more discerning sensibility.

9. “Ain’t Living Long Like This” (Waylon Jennings)

Though many outlaw country songs are just loosely referential to characters of the wild, wild west, “Ain’t Living Long Like This” could be the theme song for Jesse James or Billy the Kid.

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

10. “Mammas Don’t Let Your Babies Grow Up To Be Cowboys” (Waylon Jennings and Willie Nelson)

It doesn’t get more quintessential outlaw country than this track. The lyrics paint an astute portrait of just the kind of person that colors the outlaw movement: Them that don’t know him won’t like him and them that do sometimes won’t know how to take him / He ain’t wrong, he’s just different but his pride won’t let him do things to make you think he’s right.

Though the song was originally recorded by Ed Bruce and co-written with his wife Patsy Bruce, the version that found its way to the top of the charts comes 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 old faded levis and Lonestar belt buckles singing about their own tendencies to be a little flighty and a little misunderstood.

(Photo by Jim Bennett/WireImage)