4 Musical Icons Who Felt Rejected by Nashville Before Making It Big

Just as its name would suggest, Music City, USA, many musicians consider Nashville to be the end-all-be-all for country singers—unless, of course, you’re one of these musical icons who felt rejected by Nashville long before they made it big. If they had listened to the early “no’s” and “not for us’s,” the world might be missing some of the best contributions of country and Americana that the genres have to offer.

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As Stephen Leacock would say, “If at first you don’t succeed, try, try again.” As Willie Nelson might say, “If at first you don’t succeed, lie down in the middle of Broadway, then brush yourself off and go back into Tootsie’s for another drink.”

Willie Nelson

Willie Nelson has undoubtedly shaped country music for the better. But as a struggling songwriter in the late 1950s, Nelson thought the genre (and its mecca, Nashville, Tennessee) might be better off without him. Disheartened at the lack of income from his budding musical career and deep in the throes of alcoholism, Nelson decided to lie down in the middle of Broadway, Nashville’s musical thoroughfare, and wait for a car to usher him to his end. There was only one problem: no car ever came. “There was hardly any traffic,” Nelson wrote in Me and Paul: Untold Stories of a Fabled Friendship.

 “Was I relieved? Was I disappointed? Can’t say for sure. All I know is that I got up, went back to Tootsie’s, and had another drink,” he continued. And thank goodness he did. A few short years later, he would sign a lucrative deal with RCA Victor on the advice of Chet Atkins, and the rest is country music history.

Waylon Jennings

Artists like Waylon Jennings and his long-time friend and colleague, Willie Nelson, weren’t “outlaw country” because they were literally breaking the law. (Okay, they did some of that, too.) The descriptor came from their stark contrast to the polished, commercial-friendly country coming out of Nashville in the 1960s and ‘70s. Jennings is a unique addition to this Nashville reject list in so much that the city didn’t necessarily reject him. He rejected it before the city ever got the chance.

In Nelson’s 2015 memoir, It’s a Long Story: My Life, Nelson recalled meeting Jennings, who asked him whether moving to Nashville was a good idea. “Well, sir,” he told Jennings, “after having been in Nashville for some time, I don’t see it as your town. Nashville will wanna mold you, and you don’t need no molding. You need to stay away from Nashville.” So he did, and what a fortuitous career move that turned out to be.

Chris Stapleton

Nashville’s Bluebird Cafe is a hallowed institution where artists big and small can vie for a spot on the venue’s open mic line-up. Artists travel for miles just for a chance to perform in the intimate listening room, and a young Chris Stapleton was no exception. The “Tennessee Whiskey” singer drove upwards of four hours from his eastern Kentucky home for a shot at the mic. If attendees who signed up for the open mic didn’t get to go on stage that night, the venue typically awarded them a pass guaranteeing a performance slot at the next open mic night.

However, the following week, Stapleton was rejected by the Nashville venue once again. “It bothered me more that they broke the deal, that they broke the accord, than actually not getting to play,” he recalled in a 2024 appearance on the Howard Stern Show. Stapleton said the experience made him work even harder, and these days, the Bluebird and its attendees would trip over their own feet rushing toward the opportunity to hear him in such a small, cozy setting.

Dwight Yoakam

Before he made it big with hits like “Guitars & Cadillacs” and “Streets of Bakersfield,” Dwight Yoakam was a country picker without a specific geographical sound to lean on. Born in eastern Kentucky and raised in central Ohio, Yoakam struggled to find his footing in Nashville at a time when pop-sensible country music dominated the mainstream. He moved to the West Coast to cut his teeth there, where he would ultimately make the connections that would give him his big break.

“What I didn’t realize was that Nashville has never really been about live performance,” Yoakam told Dan Rather in an AXS TV interview. “It was about song publishing and songwriting. That’s the access point.” As a performer blending styles of Appalachian folk, honky tonk, and the Bakersfield sound, Yoakam was hardly welcomed into Nashville with open arms. By the late 1980s, Yoakam had found his place in the modern country market, but the country artist had to work through plenty of Nashville rejection before he got there.

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