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Willie Nelson: Country Outlaw

I grew up in the "classic rock" era, but I love music of every genre. I love sharing my old favorites while still discovering new artists.

An Original Outlaw Country Artist

It seems like being crazy, or out of his mind, is a topic Willie Nelson has often addressed in his songs, especially in the early days of his "overnight success" as a recording artist. It had taken many years and many records before he suddenly shot to fame with his 18th album, Red Headed Stranger.

As one of the original "outlaw country" artists, Willie Nelson helped revolutionize country music. Willie may not be crazy, but his long and illustrious career has taken some wild turns.


It is amazing to me that, after all these years, when people think of a song about being crazy, the first one most people think of is “Crazy,” sung by Patsy Cline in 1962. I imagine that most true Willie Nelson fans know that Willie wrote that hit song.

Back in those days, he could only dream of the super stardom he achieved in later years. Then a struggling songwriter, Willie also recorded “Crazy” in 1962. It was on his debut album ...And Then I Wrote. Willie’s version of the song didn’t get much acclaim, but it was to his benefit that Pasty had such a huge hit with it.

Crazy followed on the heels of another song that Willie wrote and somebody else made a hit. "Hello Walls" was a huge hit for Faron Young in 1961.

The Early Years

While Willie Nelson had success as a songwriter in the early days of his career, he didn’t get a lot of recognition as a musician. He recorded over a dozen albums with RCA records. He did get on the country music charts a few times, but overall Willie was frustrated. He wanted more creative control over his music.

Shotgun Willie

Willie signed with Atlantic records in 1973; his first album with them was Shotgun Willie. It was a very different style than the albums he’d made with RCA. Waylon Jennings and Jessi Colter collaborated with him on the project playing guitar and singing on the album.

Kris Kristofferson later told him the song "Shotgun Willie" was '"mind farts." Willie thought of it more as clearing his throat for what was to come.

While being crazy is not specifically mentioned in "Shotgun Willie," it does sound like he has a tenuous grip on reality.

Phases and Stages

Shotgun Willie wasn't a huge commercial success, but having the freedom to play music the way he liked it energized Willie. It got good reviews and attracted a younger audience. A concept album, Phases and Stages, soon followed. It is still one of my personal favorites. It tells the story of a divorce; side A is the woman's story, side B the man's perspective.

These are considered some of the first “outlaw country” albums. They marked a huge change in the direction of Willie's career.

Red Headed Stranger

After the success of his recordings with Atlantic Records, Willie signed a contract with Columbia Records. They promised him complete creative control over his work. His next concept album was Red Headed Stranger. Through songs, the album tells the tale of a preacher who kills his wife and her lover (and some other people) after she leaves him.

The recording is a stark departure from that old Nashville sound. It has been described as "bare bones" mostly featuring Willie's sister Bobby Nelson on piano and Willie singing and playing guitar. Most of the songs are covers, including the hit single "Blue Eyes Cryin' in the Rain." They are loosely stitched together by the theme song penned by Willie, "The Time of the Preacher."

Red Headed Stranger was a blockbuster among both country music and mainstream audiences. It was certified multi-platinum. It made Willie Nelson one of the most recognized names in country music.

"Time of the Preacher" from Redheaded Stranger

The Sound in Your Mind

Willie's second album with Columbia, released in 1976, was The Sound in Your Mind. Many of the tracks on this record were not written by him. "I’d Have to Be Crazy" was written by his friend, Steven Fromholz, who also sang back-up on the song.

Still, it seems perfectly suited to his voice, and it sounds as if it could have been written about him. I can picture him doing the things described in this song.

"I'd Have to Be Crazy"

I'll Always Love the Old Outlaw

Willie has gone on to make a lot of good records, and maybe some not so good. As the 1980s and '90s rolled around, and Willie Nelson got used to fame and fortune, he didn't have much to rebel against anymore. I felt like he got a little more lazy and a lot less particular about his song choices.

Who can blame him really? What with being sued by the IRS and being a big star, a cannabis activist, and then the health issues he's had recently, I guess he's had his hands full. I'm not saying he doesn't still do good music, but for me I don't think it can ever match those crazy, long-ago days when I was young and he was an outlaw.

"I’ve Always Been Crazy"

This is a song by Willie's good friend, partner in crime and fellow outlaw, Waylon Jennings. And it is a great crazy song. Just think of it as a bonus.

More About Outlaw Country Music

  • Outlaw Country Music in the 1970s
    Country artists began to rebel against formulaic convention by the early 1970s, leading to "Outlaw Country" being popularized by artists like Johnny Cash, Waylon Jennings, and more.


Pat Raymond on November 19, 2019:

I could listen to Willie play the guitar all day. No one plays it like he does.

Shauna L Bowling from Central Florida on June 14, 2018:

Willie's one of my favorite country artists. I've seen him in concert four times. I don't think he's crazy. He simply lives life the way he sees fit and to hell with what others think!

Dianna Mendez on June 13, 2018:

You gotta admire the guy for his uniqueness and boldness as a singer. A little crazy -- yes. I own his gospel CD and it bring out his deeper thoughts on life, very sound.

Sherry Hewins (author) from Sierra Foothills, CA on June 03, 2018:

I can see the resemblance. I did really enjoy the albums I talked about in the article.

Don A. Hoglund from Wisconsin Rapids on June 03, 2018:

I recognize Willie Nelson as an important figure in country music but have not been a real fan. Oddly about 20 years ago I had people stop me and say I look like Willie Nelson.

Jackie Lynnley from the beautiful south on May 30, 2018:

Willie nelson is one of the few older country singers that I do like. Of course no one can do that song like Patsy but I do enjoy hearing Willie do it too.

Sherry Hewins (author) from Sierra Foothills, CA on May 30, 2018:

Patsys' sure had the edge with thay beautiful voice of hers, but without Willie there would have been no song to sing.

Brian Leekley from Bainbridge Island, Washington, USA on May 29, 2018:

I just listened to the Willie Nelson and the Patsy Cline 1961 versions of Crazy one after the other. Nelson's seemed like a nice slow-dance song. Cline's made me feel heartache and, as usual, almost brought tears to my eyes.

Some other songs about being crazy: Danielle Nicole Band "Blind, Crippled and Crazy"; Leonard Cohen "Crazy to Love You"; Paul Simon "Still Crazy After All These Years".