About the song

When we speak of Waylon Jennings, we’re talking about the very heart and soul of the Outlaw Country movement, a period in the 1970s when artists fought for, and won, creative control over their music, breaking free from the rigid structures of Nashville’s “establishment.” An “Outlaw Shirt” represents that rejection of conformity – it’s worn, it’s comfortable, it’s real, and it doesn’t try to impress anyone it doesn’t want to. It’s the opposite of a rhinestone suit; it’s a statement of rugged individualism and uncompromising artistic integrity.

Imagine a song that delves into what such a shirt would symbolize: perhaps the scars and stories it carries from years on the road, the dust of countless honky-tonks, the sweat from passionate performances, and the quiet dignity of a man who makes his own rules. The “Outlaw Shirt” isn’t about being literally criminal; it’s about being true to oneself, even when that means going against the grain. It’s about honesty in music, independence in business, and authenticity in life. It speaks to the man who preferred to record with his own band, choose his own songs, and produce his own sound, rather than adhere to the polished, often formulaic, approach of the Nashville machine.

Waylon Jennings’ vocal performance was the embodiment of this “Outlaw” spirit. His deep, resonant baritone, often laced with a rebellious growl and a touch of world-weariness, was as distinctive and untamed as the image he projected. He didn’t sing; he testified. Every note was imbued with a sense of conviction, a refusal to compromise, and an undeniable charisma that made millions believe in his truth. He could convey defiance, tenderness, and weary resignation all in the same breath, making his music feel incredibly real and deeply personal.

The musical arrangement that would accompany a song about an “Outlaw Shirt” would undoubtedly be the signature Waylon sound: a driving, rhythmic foundation, often featuring a prominent, gritty electric guitar that echoed his rebellious spirit, alongside a solid bass line and drums that laid down a no-nonsense beat. It would be stripped down, raw, and powerful, prioritizing feel and authenticity over slick production. It would be music for the open road, for late nights, and for telling it like it is – just like the man himself.

So, while “Outlaw Shirt” might not be a track you’ll find on a “Greatest Hits” album, the concept perfectly encapsulates the enduring legacy of Waylon Jennings. He wasn’t just a singer; he was an icon who wore his independence and his artistic integrity like a second skin, proving that true freedom in music, much like a well-worn shirt, is both comfortable and utterly distinctive.

Video

Lyrics

She said storms’ll never last
So I’m looking out the window like, when’s it gonna pass?
I need some cash, I did the math, it keeps ending in subtraction
Is it fate or just the laws of attraction? I’ll never know
Pa’s tracks, fast lane, cocaine dealer
Tryin’ to ease this pain with these painkillers
I don’t want my soul to be stained to obtain my wealth
I couldn’t learn from his mistakes, I had to make em myself
And I ain’t never been scared, but reality is frightening
My three year old daughter’s name came from my indictments
Like a VH1 story with a hard ending
Shit, I’m serving a life sentence and I still got a charge pending
Seems like everywhere I go now, they watching
Hiding this pain in my eyes behind Versace’s
Can’t sleep I’m too busy chasing dreams
And the Fed’s sent a posse down like I ain’t never seen yet
Don’t you think this outlaw shit
Has gotten out of hand?
What started out to be a joke (uh huh, uh huh, they don’t understand)
The law don’t understand
I’ve always been crazy but it helped me from going insane
I grew up thinking it’s part of the game
Them outlaw’s always taught me bad guys were the Fed’s
Don’t get high on your supply, your brain will look like eggs
In a skillet, yeah, can you feel it? Forget it
80’s baby, crack era, that’s how I’ma get it
Fresh up outta jail, new plan, new man
But I can’t seem to change who I am, I’m a hustler
I’ve been running for so long from them boys
I can’t go to sleep without the noise
Television’s on, forty by my head
Laying on the couch while my shorty’s in the bed
If I stay awake ’til five, I’ll probably sell another ounce
Shoes tied tight just in case I gotta bounce
Hear their tires hit the gravel, how they know I’m back at it?
Little girl looking, “Daddy why you in the attic”? I’m hiding
Don’t you think this outlaw shit
Has gotten out of hand?
What started out to be a joke
The law don’t understand (nah)
But it’s a beautiful view when we’re looking down
From this high, over snow capped mountains (dope boys)
Crimson dyed, don’t give my momma black roses
I got a gun, but I’m not strong enough to hold it
Crimson dyed, a broken record for a token
Pay a silver dollar for another crime story
But when you’re looking down from this high
And I just made it to the clouds
And it’ll be a while before I hit the ground (let’s go)
And taking freedom from me now
Would be like taking water from the Nile
‘Cause the river still flows
From a story that a dam couldn’t hold
Aight, grandpa, it’s your turn
Don’t you think this outlaw shit
Has gotten out of hand?
What started out to be a joke
The law don’t understand

By tam