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.