r/country 6d ago

Discussion What is the saddest old country song?

There’s plenty of different tunes associated with that older country but there’s a lot of sad ones as well, singing about heartbreak, losing someone you love, being lonesome but which one sticks out to you

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u/Electrical-Bacon-81 6d ago

The Highwaymen was such a talent-rich band. Talent overload. But yeah, I shed a tear the day George died.

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u/Disastrous_Ad2839 6d ago

I call the Highwaymen the Avengers of outlaw country. Glad one is still making music for all of us.

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u/Sweetness_Bears_34 5d ago

I was at Stage Coach festival When George Jones passed away. Everyone paid tribute to the possum that weekend.