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Country Music

The Highwaymen – Ragged Old Flag

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Introduction

“Ragged Old Flag” is one of those songs that reaches into your heart, stirring up deep feelings of patriotism, respect, and reflection. When you listen to this song, it’s hard not to feel a connection to the pride, resilience, and sometimes bittersweet journey of a nation. Originally written and performed by Johnny Cash, this particular version by The Highwaymen—a legendary group consisting of Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson—carries a unique weight. These men, icons in their own right, bring a weathered wisdom to this rendition, making it feel like you’re sitting with old friends who’ve seen life’s ups and downs, sharing a story that’s personal yet universal.

At its core, “Ragged Old Flag” is not just about a piece of cloth; it’s about what that cloth represents. It’s about the strength of a country, and the struggles and sacrifices that have gone into making it what it is today. The song narrates the story of a man who stops in a small-town courthouse and speaks with an older man about the flag flying outside—a flag that’s weathered, worn, and full of battle scars. But, like the country it represents, it still stands proud.

The way The Highwaymen sing this song feels like a warm, intimate conversation. It’s slow, deliberate, and reflective. Cash’s deep, gravelly voice, in particular, brings a gravity to the lyrics that few others could match. Each word feels like it carries a lifetime of meaning, as if they’re not just singing about the flag but about their own personal experiences of seeing America through its best and worst moments.

What makes this song so special is how it evokes a feeling of collective memory. As you listen, you can almost see the imagery: the battles fought, the victories celebrated, and the losses mourned. It’s a reminder of both the beauty and the pain that come with patriotism. The ragged flag, with all its imperfections, still flies—just like the country it represents, imperfect but enduring.

Listening to The Highwaymen’s rendition of “Ragged Old Flag” also feels particularly poignant because these four men, who have each seen their fair share of life’s trials, bring authenticity and sincerity to the performance. There’s no glossing over the hardships, no sugar-coating the past. Instead, it’s a song that speaks to the hard-won lessons of history and the enduring hope that still flies high.

If you’re someone who feels deeply connected to the story of America, or even if you just appreciate a song that tells a powerful story, “Ragged Old Flag” is bound to leave a mark on your heart. It’s not just a tribute to a flag but a tribute to the enduring spirit of a people who continue to strive for something better, no matter how many times they get knocked down.

Video

Lyrics

I walked through a county courthouse square
On a park bench an old man was sitting there
I said, your old courthouse is kinda run down
He said, naw, it’ll do for our little town
I said, your old flagpole has leaned a little bit
And that’s a ragged old flag you got hanging on it

He said, have a seat, and I sat down
Is this the first time you’ve been to our little town?
I said, I think it is
He said, I don’t like to brag
But we’re kinda proud of that ragged old flag

You see, we got a little hole in that flag there when
Washington took it across the Delaware
And it got powder-burned the night Francis Scott Key
Sat watching it writing say can you see
And it got a bad rip in New Orleans
With Packingham and Jackson tuggin’ at its seams

And it almost fell at the Alamo
Beside the texas flag, but she waved on though
She got cut with a sword at Chancellorsville
And she got cut again at Shiloh Hill
There was Robert E. Lee, Beauregard, and Bragg
And the south wind blew hard on that ragged old flag

On Flanders field in World War one
She got a big hole from a Bertha gun
She turned blood red in World War Two
She hung limp and low a time or two
She was in Korea and Vietnam
She went where she was sent by Uncle Sam

She waved from our ships upon the Briny foam
And now they’ve about quit waving her back here at home
In her own good land here she’s been abused
She’s been burned, dishonored, denied, and refused

And the government for which she stands
Is scandalized throughout the land
And she’s getting threadbare and wearing thin
But she’s in good shape for the shape she’s in
‘Cause she’s been through the fire before
And I believe she can take a whole lot more

So we raise her up every morning
We take her down every night
We don’t let her touch the ground and we fold her up right
On second thought, I do like to brag
‘Cause I’m mighty proud of that ragged old flag

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