Pick Your Favorite Country Music Songs, And We’ll Guess Your Age!
Who pushed the boundaries of country in a way that worked?

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Whether we’re talking about Johnny Cash’s landmark decision to record a live album from a prison complex, the “cowpunk” pioneered by Steve Earle, or the mind-bending experiments of Sturgill Simpson, some artists have found truly unexpected ways to innovate the genre. Which one meant the most to you may depend on your age.
Tim Mosenfelder/Getty Images
Tim Mosenfelder/Getty Images
Who pushed the boundaries of country in a way that worked?
- Sturgill Simpson – “Turtles All The Way Down”
- Johnny Cash – “Folsom Prison Blues”
- Steve Earle – “The Revolution Starts Now”
- Kenny Rogers – “The Gambler”
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