3 Country Singers That Broke Out of Their Box and Became Legends Because of It

These three country singers decided to forge their own path. What could’ve been career-killing moves proved to be just the ticket, taking them from star to legend.

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Willie Nelson

Willie Nelson started his career as a buttoned-up country singer playing into the “Nashville” sound. He had slicked-back hair and looked the picture of refinement; a very different image than we would associate with him now. Today, Nelson’s character is one of carefree exuberance: rebellion and fervor for life. Long braids, weed, and songs about gritty lifestyles: that’s what we associate with Nelson now.

When he first made that switch, though, no one could’ve foreseen how important it would be to his career. In fact, he could’ve completely killed any chance of becoming a top country star after he moved back to Texas, grew out his hair, and started leaning into the outlaw of it all. That bold move made Nelson the artist we know and love today.

Shania Twain

Shania Twain challenged the conventions of what could be considered “country” and what could not. She moved further into the pop realm than any other country singer had dared to go before. By blending genre lines unabashedly, she paved the way for most modern country artists, all of whom imbue their music with a crossover element.

Her pop twist made her one of the most successful female artists in any genre ever. She connected with a wide array of listeners once she started bringing in other flavors. Country isn’t always kind to blurred lines, but Twain proved what can happen when we push boundaries.

Taylor Swift

Next, an obvious choice: Taylor Swift. She picked up where Twain left off. Instead of just teetering on the line between pop and country, Swift fully leaped. She left her countryism behind for full-blown, stadium-filling pop. At the time, her country purist fans were likely sad to see her go, but no one can deny it was the right move. It helped her become the biggest star in the world.

Pop music gave Swift an even bigger audience than she already had. Even as a country star, she pulled in pop listeners. But once she broke through that barrier, nothing stopped her meteoric rise. No scandal or bad reviews could keep this legendary singer down for long. She’s come back from every roadblock stronger than before. Pop music gave her the armor to endure.

(Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)