2. “Teardrops On My Guitar”
When coming up with this list, I already knew which two songs were going to be contending for first and second place. After much listening and debating though, I eventually decided to put “Teardrops On My Guitar” at #2 within my rankings.
As far as Taylor Swift’s songs go, this is easily one of her most iconic. There is something about hearing those first few lines and you’re immediately hooked. With lines like “I’ll bet she’s beautiful/ that girl he talks to/ but she’s got everything I have to live without,” and “I wonder if he knows he’s all I think about at night,” you can feel the hurt and sadness in her words.
This is another song I remember listening to over and over again because it captures that feeling of being a teenager and wanting someone who either doesn’t want you or won’t notice you. It’s such a universal feeling which really fueled this song’s popularity amidst its release. Plus it was the second single of her album so people were waiting and hyped for it.
“Teardrops On My Guitar” also got a pop version of it and had an amazing music video featuring Tyler Hilton as Drew. In 2007, this song was everything a lot of teenage girls were feeling and I feel like that’s part of the reason why it became such a smash hit for Taylor Swift.
The song is dramatic and fun while also being surprisingly sad which is just a testament to Taylor’s songwriting. Regardless of whether you were introduced to Taylor during this era or not, this song still remains a classic in her discography.