I’ve got “Either Way” by Chris Stapleton.

https://youtu.be/F0hdQ7latVY

Whiskey and You is no rollicking good time either. But “Either Way” is rough.

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You know me like that.

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At the risk of sounding like Frank suggesting a Zeppelin song for best country song I’ll say Black Muddy River by the Dead is a song I consider to have pretty country roots that is kinda depressing but I love it.

I know it’s supposed to be uplifting and I can’t remember the name but the cancer song from Tim McGraw has to be in the team photo. I don’t think I’m a fan of his but I remember it being decent.

I’m not a country guy tho. I’ll check your suggestion out after a few more whiskey pours tonight and after this Mavs Nugs game I foolishly bet on

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Fare you well, fare you well
I love you more than words can tell
Listen to the river sing sweet songs
To rock my soul

Is High Cost of Living a depressing song? I just think of it as a cool one and one of the only semi recent country songs I’ve heard that I like

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Fare you well, fare you well
I love you more than words can tell
Listen to the river sing sweet songs
To rock my soul

Tim McGraw song is Live Like You Were Dyin’

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You know me like that.

Yeah that’s the one. Been a few years since I heard it but I remember liking it while generally disliking many others my friends suggested over the years

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Fare you well, fare you well
I love you more than words can tell
Listen to the river sing sweet songs
To rock my soul

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Anybody here seen my old friend Bobby?
Can you tell me where he's gone?
I thought I saw him walkin' up to The Hill
With Elon, Tulsi, and Don

The chorus isn't bad, but his leather cowboy hat is unforgivable.

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I can’t say I’ve seen the video. 90% of my country music listening and definitely all of it post 1980 came from the rednecks in Ft Polk blasting it on speakers outside of the barracks from 2008-2011

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Fare you well, fare you well
I love you more than words can tell
Listen to the river sing sweet songs
To rock my soul

Go Rest High On That Mountain - Vince Gill

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"All crowds boycotting football games shouldn't care who sings or takes a knee because they aren't watching." - Nas

Tim McGraw- "Don't Take the Girl"

https://www.youtube.com/watch?v=-vn6QdqxK3g

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Sherman remarked, "Well, Grant, we've had the devil's own day, haven't we?" Grant looked up. "Yes," he replied, followed by a puff. "Yes. Lick 'em tomorrow, though."

Teddy Bear (in part)

But you see, I get lonely and it helps to talk
'Cause that's about all I can do, I'm crippled, and, I can't walk!"
I came back and told him to fire up that mike
And I'd talk to him, as long as he liked

"This was my dad's radio", the little boy said
"But I guess it's mine and mom's now, 'cause my daddy's dead!"
"Dad had a wreck about a month ago
He was trying to get home in a blindin' snow

Mom has to work now, to make ends meet
And I'm not much help, with my two crippled feet!"
"She says not to worry that we'll make it alright
But, I hear her crying, sometimes late at night

You know there's just one thing I want more than anything else to see
Aw, I know you guys are too busy to bother with me!"
"But, you see, my dad used to take me for rides when he was home
But, I guess that's all over now, since my daddy's gone

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"All crowds boycotting football games shouldn't care who sings or takes a knee because they aren't watching." - Nas

"Teddy Bear" may be the worst song ever recorded. Part of the "Convoy" and CB radio craze of the 70s.

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Anybody here seen my old friend Bobby?
Can you tell me where he's gone?
I thought I saw him walkin' up to The Hill
With Elon, Tulsi, and Don

If You’re Reading This is Tim McGraw’s most depressing song.

Dress Blues by Zac Brown Band for honorable mention in the military/war subsection.

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Country Death Song- Violent Femmes

https://www.youtube.com/watch?v=FWZf_RBcB_Y

Pretty much any song by Reba

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"He is a loathsome, offensive brute
--yet I can't look away."

Billy, Don't be a Hero

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“Mr. Trump is unfit for our nation’s highest office.”- JD Vance
“My god, what an !diot.”- JD Vance tweet on Trump
“I’m a ‘Never Trump’ guy”- JD Vance

I got you beat by a country mile

https://www.youtube.com/watch?v=nLh5vbBLpxI

Alissa lies.

or this one

The Little Girl

https://www.youtube.com/watch?v=K1j669NVNzM

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When I am stuck and need to figure something out I always remember the Immortal words of Socrates when he said:"I just drank what?"

I don't view that song as depressing.

Tonight I wanna Cry by Keith Urban

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"I give you my word as a Biden"

Technically not a country song, but combine Bruce Hornsby The National The Grateful Dead, and Bon Iver, I'm all in.
https://www.youtube.com/watch?v=kPS1_j8lIf4

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Just chillin' like Garret Quillin.

this one : not even close -

https://www.youtube.com/watch?v=UbOow2mkxck

Live Like you were dyin is a really good call. God, I hate song.

There's this one, which is a double qualifier.....most depressing and DUMBEST country song.
https://www.youtube.com/watch?v=k2sz5Qw_4lE

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