Co-written by Taylor Swift and Liz Rose and produced by Nathan Chapman, "Teardrops on My Guitar" is Swift's first song to break into the top 20 on Billboard's Hot 100. Singing about a boy classmate named Drew that she was crazy about but who was completely unaware of her true feelings, "He's the reason for the teardrops on my guitar/The only thing that keeps me wishing on a wishing star." Drew continued to speak about his girlfriend to Swift, something she pretended to be endeared by. Years afterwards, Drew appeared at Swift's house, but Swift rejected him. Musically, the track is soft accompanied by a gentle acoustic guitar. Some critics have questioned the song's classification as country music.
"Teardrops on My Guitar" was released on February 19, 2007 by Big Machine Records, as the second single from Swift's eponymous studio album, Taylor Swift (2006). The song was later included on the international release of Swift's second studio album, Fearless (2008). The song is considered to be Swift's breakthrough single as it significantly boosted her popularity as an upcoming star. "Teardrops on My Guitar" was a commercial success, peaking at number 13 on the Billboard Hot 100, becoming the best-charting single from Taylor Swift on the chart. The single was also certified double platinum by the Recording Industry Association of America (RIAA). Its music video was directed by Trey Fanjoy which received a nomination for MTV Video Music Award for Best New Artist, but lost to Tokio Hotel's music video for "Ready, Set, Go!".
"Teardrops on My Guitar" lyrics:
Drew looks at me
I fake a smile so he won't see
That I want and I'm needin'
Everything that we should be
I'll bet she's beautiful
That girl he talks about
And she's got everything
That I have to live without
Drew talks to me
Drew talks to me, I laugh 'cause it's just so funny version
Drew talks to me, I laugh 'cause it's so damn funny version
I can't even see
Anyone when he's with me
He says he's so in love
He's finally got it right
I wonder if he knows
He's all I think about at night
He's the reason for the teardrops on my guitar
The only thing that keeps me wishing on a wishing star
He's the song in the car I keep singing
Don't know why I do
Drew walks by me
Can he tell that I can't breathe?
And there he goes, so perfectly
The kind of flawless I wish I could be
She better hold him tight
Give him all her love
Look in those beautiful eyes
And know she's lucky 'cause
He's the reason for the teardrops on my guitar
The only thing that keeps me wishing on a wishing star
He's the song in the car I keep singing
Don't know why I do
So I drive home alone
As I turn out the light
I'll put his picture down
And maybe get some sleep tonight
'Cuz he's the reason for the teardrops on my guitar
The only one who's got enough of me to break my heart
He's the song in the car I keep singing
Don't know why I do
He's the time taken up but there's never enough
And he's all that I need to fall into
Drew looks at me
I fake a smile so he won't see.
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- Xena
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(Los Angeles, United States)