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Teardrops On My Guitar

Single | Taylor Swift (2006)

“Teardrops On My Guitar” is Taylor’s breakthrough hit from her debut studio album, Taylor Swift (2006). It illustrates the unrequited love she felt for her classmate Drew Hardwick. She said that Drew would often ask her for date ideas for his girlfriend, and she would give him advice to be a good friend.

Taylor was 17 when the song was released. It made her the first teen country star to make a major crossover into the pop charts since LeAnn Rimes. This seemed like a pretty big deal at the time, but her breakout was just one step in Taylor’s journey toward becoming one of the biggest stars of all time.

Background and Lyrical Theme

Taylor was inspired to write “Teardrops On My Guitar” about her experience with Drew, a classmate of hers whom she had feelings for. During their freshman year at Hendersonville High School in Hendersonville, Tennessee, Taylor and Drew sat beside each other in class every day. The two became friends, although she secretly desired for them to become a couple. Because of Drew’s unawareness, he would frequently speak to Taylor about another girl he had feelings for, something she pretended to be endeared by. Drew and his crush eventually developed a relationship which lasted for a few years. At a concert, she told fans:

«I was that ‘friend,’ you know, that girl who’s your friend. He had this awesome girlfriend who he would tell me about every single day. And, you know, I was that girl that he would go to and be like, ‘What should I get her for Valentine’s Day? I have to make this Valentine’s Day so awesome! It’s her birthday, what should I do? What would the perfect gift for a girl be?’ And of course I’d give him the most awesome ideas, awesome plans, like I would want them! And it didn’t end up like in the end of the chick-flick where they get together in the end. It didn’t happen like that. So I wrote a ong and I put it out on the radio, and they’re still together!»

Taylor Swift

Taylor never confessed her feelings to Drew. By the release of Taylor Swift, he remained unaware of her intentions or of the song and continued his relationship. Upon the single release of “Teardrops On My Guitar” however, Drew attempted to contact Taylor via phone calls, which she did not respond to; he then left voicemails, but she felt too awkward to call back. She said, “I think right under his driver’s license where it says ‘Drew Hardwick’ it says, ‘Taylor wrote a song about me.’ But I haven’t talked to him in a while, I haven’t talked to him for probably a year and a half, but I’ve heard through the grape vine that he’s very well aware of [the song.] But, you know, it’s crazy how having a top five hit with a song won’t get you over somebody.”

Two Years Later

Two years after the album’s release, as Taylor was leaving her house to attend a Nashville Predators hockey game with Kellie Pickler and Carrie Underwood, Drew appeared at her driveway with a friend of his. After two and a half years of not speaking and Taylor gaining a significant amount of fame, the two conversed. In an interview with the HMV Magazine, she recalled:

«About two years after the album came out in the States, he showed up in my driveway. Apparently, he and his girlfriend had broken up, so that was his first stop when he was back in town. I was like 'You are so late, y'know? If you'd stopped by right after the album came out then that would be one thing, but…' I remember reading on his MySpace page one time, 'My name's Drew and I have a famous song written about me. Email me and I'll give you details.' I was like, 'Right, wow, note taken.'»

Taylor Swift

She conjectured multiple theories as to why Drew appeared at her house. One of them was that he was attempting to prove to his friend that he was indeed the subject of “Teardrops On My Guitar”. Other possibilities was that he wanted to rebuild their friendship or believed Taylor was still pining away from him. Taylor said it would have been poetic if he approached her upon the album’s release and she would have accepted, but that she had already moved on. She cited “Teardrops On My Guitar” as an example of how she expresses her sentiments in songs and sometimes in no other manner. She was not afraid of using Drew’s first name on the track and, therefore, believed it was very honest and susceptible, something she adored.

Music Video

The accompanying video to “Teardrops On My Guitar” was directed by Trey Fanjoy, who had also directed the video for Taylor’s first single, “Tim McGraw“. Taylor said the video centered around unrequited love. Some of her associates first believed the video should have been set in a prior era. They then thought about filming the video at a large city. However, Taylor wanted to go back to basics and keep the song’s integrity by filming the video in Nashville, Tennessee. American singer and actor Tyler Hilton portrayed Drew. He was cast because of prior interactions with Taylor, they had a mutual fondness for each other’s music. Taking into account his acting on the television series One Tree Hill and the film Walk the Line (2005), Taylor asked him to participate in the video after he attended and performed at one of her concerts. The video was filmed on January 9, 2007, at Hume-Fogg High School; the drama room was transformed to simulate a bedroom for the performance scenes. It received a nomination for “Number One Streamed Music Video” at the web-hosted 2007 CMT Online Awards and was also nominated for the MTV Video Music Award for “Best New Artist” in 2008. As of May 20, 2021, the video has over 153 million views.

Live Performances

Taylor first performed “Teardrops On My Guitar” as she opened for Rascal Flatts on several dates, from October 19 to November 3, 2006, included on the “Me and My Gang Tour” (2006-2007). She also performed the song when she served as opening act on twenty dates for George Strait’s 2007 United States tour, and selected dates for Brad Paisley’s “Bonfires & Amplifiers Tour” in 2007. During mid-2007, Taylor engaged as the opening act on several dates for Tim McGraw’s and Faith Hill’s joint tour, “Soul2Soul II Tour” (2006-2007), and performed the song while she was again opening for Rascal Flatts for their “Still Feels Good Tour” in 2008. When promoting the single, Taylor performed it on numerous venues, including at the Apple Store in SoHo, New York, which was recorded and released as a live extended play (EP), iTunes Live from SoHo, exclusively sold through the iTunes Store. Since completing promotion for Taylor Swift and its corresponding singles, Taylor has also performed “Teardrops On My Guitar” as a duet with English rock band Def Leppard on CMT Crossroads.

Taylor performed the song on all venues of her first headlining concert tour, the “Fearless Tour,” which extended from April 2009 to June 2010. Later, Taylor performed the song for the first time in three years during “The RED Tour“‘s stop in San Antonio on May 22, 2013. Five years after that, she sang the song at the Denver stop on her “reputation Stadium Tour” on May 25, 2018. “Teardrops On My Guitar” was the second surprise song of the night on May 5, 2023, in Nashville and on February 18, 2024, in Melbourne on Taylor’s “The Eras Tour” (2023-2024). On July 23, 2024, she mashed it up with “The Last Time” (2012) in Hamburg.

Critical Reception

“Teardrops On My Guitar” has received acclaim from contemporary critics. Regarding the song’s musical genre, Roger Holland of PopMatters believed there was no reason for Taylor to limit herself into only the country music or why she should be a country artist at all. Deborah Evans Price of Billboard stated that “Teardrops On My Guitar” showcased the same qualities as “Tim McGraw” (2006) – solid gifts of songwriting and time-halting earnest and pure voice. Price declared that the song made obvious that Taylor would have much success for years to come at the time. Chuck Taylor, also of Billboard, reviewed the pop version release of “Teardrops On My Guitar”, and stated it was a “beautiful mainstream intro to an artist whose rise is ably exemplified by her last name.” In 2019, Insider named “Teardrops On My Guitar” one of the fourteen best songs written by teenagers. It also ranked at No. 47 on Teen Vogue‘s “91 Best Songs About Unrequited Love” list, while Taylor’s 2009 single “You Belong With Me” topped the list.

Commercial Performance

“Teardrops On My Guitar” is considered to be Taylor’s breakthrough single, as it spread her popularity throughout the United States. It is her first song to appear on the Billboard Year-End Hot 100 charts. After thirty-seven weeks upon the chart, on the week ending February 23, 2008, the song reached its peak at No. 13 on the Billboard Hot 100, becoming the highest-charting single from Taylor Swift on the chart.

On the Billboard Hot Country Songs chart, “Teardrops On My Guitar” reached its peak at No. 2 on the Billboard Hot Country Songs. The song was a crossover hit as well, peaking at No. 7 on Billboard Pop Songs and spending twenty-one weeks on the chart. In Canada, the song peaked at No. 45 on the week ending August 12, 2007. The single was certified Platinum by Music Canada for sales of 80,000 digital downloads. Released as the third single from Taylor’s second studio album Fearless (2008), the track debuted at No. 100 on the week ending April 21, 2009 and peaked at No. 51 on the week ending May 17, 2009 in United Kingdom.

The Sad Ending of the Story

Drew later went on to join the United States Navy. In 2015, he and his wife Joni were arrested in Hendersonville, Tennessee, on charges of aggravated child abuse.

Lyrics

[Verse 1]
Drew looks at me, I fake a smile so he won’t see
That I want and I’m needing 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

[Verse 2]
Drew talks to me, I laugh cuz it’s just so funny
That 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

[Chorus]
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

[Verse 3]
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’d better hold him tight, give him all her love
Look in those beautiful eyes and know she’s lucky ’cause

[Chorus]
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

[Bridge]
So I drive home alone, as I turn out the light
I’ll put his picture down and maybe
Get some sleep tonight

[Final Chorus]
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…

[Outro]
Drew looks at me, I fake a smile so he won’t see