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Taylor Swift · S1 E6
Nashville Weekends
Flying to Nashville alone at 11, 12, 13 years old to pitch songs on Music Row — and being told no, every time.
She is eleven years old and carrying a folder of handwritten songs down Music Row. She knocks on the first door, and nobody is expecting her.
"Teardrops on My Guitar" -- Taylor Swift (Taylor Swift, 2007). Her second single: a girl with a crush on a boy named Drew who friend-zones her every day without realizing it. She goes home and turns the conversation into a top-fifteen country hit. This is the Nashville Weekends skill in its purest form.
Teardrops on My Guitar
"Teardrops on My Guitar" is about Drew Hardwick, a real boy at Hendersonville High School who tells Taylor every day about a girl he likes, not realizing it is her. She goes home from those conversations and writes what may be the most efficient example of her early method: one specific, documented real moment, rendered so precisely that it becomes universal. The song peaks at number thirteen on the Hot Country Songs chart and crosses to number forty on the Hot 100. Drew finds out about the song from the radio and calls to say he had no idea.
Music Row
From age eleven to thirteen, Taylor and Andrea fly from Wyomissing to Nashville on weekends: down on Friday, meetings on Saturday, home Sunday in time for school Monday. She pitches songs at DreamWorks Nashville, Mercury Nashville, and several independent labels. The answer is always the same: talented, but too young. At thirteen, she co-writes "The Outside" with Liz Rose, her first completed original co-write.
TAP TO REVEAL: A major Nashville label offers thirteen-year-old Taylor Swift a record deal. She turns it down. Why?
“Every single label in Nashville told us no. I kept thinking: they're not saying no to me, they're saying no to a version of me that doesn't exist yet. I just had to make her exist faster.”
— Taylor Swift, Billboard, 2014
Bonus Listening
"Picture to Burn" (Taylor Swift, 2006). The defiant side of her debut album: a song about a boy who did not treat her right, delivered with the energy of someone who has decided rejection is information, not a verdict.
"Teardrops on My Guitar" is about a real person at Hendersonville High School. What happened when he found out the song was about him?
The meetings are done and the deals that did not work are behind her. The family is about to pack everything into a move to Hendersonville, Tennessee, betting their entire lives on a state where none of them have ever lived.
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