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Today, Dolly Parton is one of the most successful singers in the world. But she had her fair share of struggles in her early career. As a teenager, she worked hard to get in the door of countless record labels. One finally gave her a shot. But after just one record, they decided to cut ties.  

Dolly Parton signed with Tree Publishing as a songwriter

Parton’s Uncle Bill used to act as the “Jolene” singer’s manager. He and Parton knocked on doors all over Nashville. One day, the duo set their sights on Tree Publishing. Buddy Killen of Tree Publishing had off-handedly told Bill to stop by his office sometime, perhaps never thinking Bill would actually show up. 

“He obviously didn’t know Uncle Bill,” Parton wrote in her 1994 memoir, Dolly: My Life and Other Unfinished Business. “We walked into the outer office, with our guitars in tow, and proudly announced ourselves. We thought we gave off an air of serious music professionals. Looking back, I’m sure everybody in that office could recognize us as a pair of backwoods doorknockers with more brass than credentials.”

Parton and her Uncle Bill told the woman at the front desk that they were there to see Killen. She told the duo that Mr. Killen was in meetings and appointments all day. But that didn’t discourage Parton and her uncle. They waited until the very end of the day when Killen was free to see them.  

“When we first walked into the outer office, I had been a little bit nervous, but by now I felt like a caged animal that had been set free,” she wrote. “I flapped open the lid of my cardboard guitar case and whipped out my old Martin. Mr. Killen seemed a little taken aback. I think he wasn’t sure whether I was going to play the guitar or brain him with it. He breathed a sigh of relief when I went into a song.”

Killen seemed to enjoy the songs Parton and her uncle had written. The “Coat of Many Colors” singer also guessed that Killen couldn’t help but admire their guts. 

Parton and Bill signed on with Tree Publishing as songwriters. 

“That was great, but there was something else that absolutely made my spirit soar,” wrote Parton. “I was to have a demo recording session for Mercury Records.”

Dolly Parton’s demo with Mercury Records 

Parton and her uncle drove back to Nashville from Sevierville (where she and her family lived) two or three more times to make the record. The “9 to 5” singer was ecstatic. 

The A side was a song that she and Bill had written called “It May Not Kill Me (But It’s Sure Gonna Hurt).” The other side had a song written by the niece and uncle duo plus another uncle named John Henry called “I Wasted My Tears (When I Cried Over You).”

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Both songs got airplay on the local radio stations. 

“I will never forget hearing ‘It May Not Kill Me’ on a Knoxville station, WIVK,” wrote Parton. “There I was, actually hearing myself sing, not on a tape or studio monitor but on a real radio station that thousands of people were listening to . . . at that very moment. I was so proud I walked around for days with my chest all stuck out. Somehow, nobody noticed.”

Tree Publishing and Mercury Records dropped Dolly and Bill 

As good as it was to hear her songs on the radio, not enough stations played Parton’s songs, nor did they play them enough. 

“The realities of the music business began to reveal themselves to me,” she wrote. “It is one thing to have a record company take a chance on an unknown and finance a record. It is quite another to get radio stations to play it. The overall response to my records had given the label little reason to pursue future recordings with me. We had all tried our best, but there’s just no way to guess what the public is going to go for at any given time.”

Though it didn’t work out back then, Parton writes that she’ll always be grateful to Killen for giving her that first opportunity.