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Should've Said No

Single | Taylor Swift (2006)

“Should’ve Said No” is track nine on Taylor’s debut studio album, Taylor Swift (2006). It was released as the album’s fifth and final single on May 19, 2008. In the song, Taylor is addressing her former boyfriend who cheated on her.

Background and Lyrical Theme

Taylor wrote “Should’ve Said No” when she was 16 years old because “something really, really dramatic and crazy” was happening to her, and she felt that she needed “to address it in the form of music”. She then called her producer and completed the song overnight. According to the Country Weekly magazine, she was inspired to write it after she discovered that her boyfriend at the time had cheated on her. Fittingly, the song’s secret message in the album lyric booklet mentions that the boy in question’s name is Sam. The first line that came to Taylor was the title, and she wrote the chorus in five minutes. She said:

«Just being a human being, I’ve realized that before every big problem you create for yourself, before every huge mess you have to clean up, there was a crucial moment where you could’ve just said no. This is a song I wrote about a guy who never should have cheated on me.»

Taylor Swift

Taylor has also said that many of the lyrics were based on actual words that she used when confronting her ex-boyfriend. She compared the song to her previous single “Picture to Burn“. While “Picture to Burn” has an “angry and I’m-done-with-him attitude”, “Should’ve Said No” is “more of a moral statement. It’s an, ‘I love you, we were awesome and great together, but you messed this up and I would still be with you’ kinda thing. You said yes, and you should’ve said no.”

Famously, her songs name names. In 2008, she told Women’s Health: “I like to encode capital letters in the printed lyrics, so they spell out phrases. I encoded the ‘Should’ve Said No’ guy’s name over and over. It was only his first name, but everyone figured it out. I’d get texts from him. He was scared out of his mind I’d crucify him on a talk show. All I could think was, ‘Well, you should’ve said no. That’s what the song is about.'”

Last Minute Addition

“Should’ve Said No” was written and recorded on the very last day of studio recording for Taylor Swift — two days before the mastering was scheduled, and booklets were about to be printed. Taylor explained:

«I wrote this song by myself, and it literally took me just 20 minutes to write before we recorded it. I was living every line in this song at the time. I wrote this song about a guy who cheated on me who shouldn't have.»

Taylor Swift

Big Machine CEO Scott Borchetta said that she called him and said she had just finished the song. He recalled that she asked first if he needed to hear it, but he told her no because she sounded so excited about it, allowing her to put it on the album right away. “That was a very real moment and I just trusted her higher instincts. For all our records I’ve left them open open until literally the last possible day because she’s always writing,” he remarked.

Music Video

Footage from Taylor’s performance at the 2008 Academy of Country Music Awards was later used as a live music video for the song. The performance begins with a hooded Taylor playing the guitar and after an on-stage costume change, she is wearing a black dress. At the end of the performance, she walks up the stairs and performs in the rain. For the country music industry, this performance solidified Taylor as the genre’s next superstar.

Live Performances

Taylor first performed “Should’ve Said No” at the 2008 Academy of Country Music Awards. She also performed the song with Jonas Brothers on the “Burning Up Tour.” The song is also included in the concert film Jonas Brothers: The 3D Concert Experience, and in the soundtrack to the movie. As for her own concerts, “Should’ve Said No” was performed as the epic encore for both the 2009 and 2010 set lists of her first concert tour, the “Fearless Tour.” She performed the song, acoustically, on selected dates of her “The RED Tour” (2013-2014), and it replaced “You Are in Love” during the first show in Santa Clara during “The 1989 World Tour” (2015). The song was also incorporated as a part of her “reputation Stadium Tour” (2018), where it was performed in a mashup with “Bad Blood“. “Should’ve Said No” was also the first surprise song of the night on May 19, 2023, in Foxborough on Taylor’s “The Eras Tour” (2023-2024). Taylor sang the song again on February 24, 2024, during her second “Eras Tour” show in Sydney. It was part of an acoustic guitar mashup, together with “You’re Not Sorry” (2008).

Critical Reception

“Should’ve Said No” received critical acclaim along with “Picture to Burn”. Roger Holland of PopMatters said that “Should’ve Said No” is “a truly splendid pop-rock song wrapped up in an almost entirely spurious country arrangement.” Chris Neal of Country Weekly believed “Should’ve Said No” and her previous single “Picture to Burn”, were the most immediately striking songs on Taylor Swift.

Commercial Performance

“Should’ve Said No” became Taylor’s second No. 1 single on the Billboard Hot Country Songs chart, and was a Top 40 hit on the Billboard Hot 100. When the song reached the Top 10 of the Hot Country Songs in July 2008, Taylor became the first solo female artist to score five top 10 hits from a debut album since the album chart was first published in 1964. Her previous four chart entries had been “Tim McGraw,” “Teardrops On My Guitar,” “Our Song” and “Picture to Burn.” An alternate version of the song was released on Taylor’s 2008 extended play Beautiful Eyes.

Lyrics

[Verse 1]
It’s strange to think the songs we used to sing
The smiles, the flowers, everything…is gone
Yesterday I found out about you
Even now just looking at you…feels wrong
You say that you’d take it all back, given one chance
It was a moment of weakness and you said yes…

[Chorus]
You should’ve said no, you should’ve gone home
You should’ve thought twice before you let it all go
You should’ve know that word, ’bout what you did with her
Would get back to me… (Get back to me)
And I should’ve been there, in the back of your mind
I shouldn’t be asking myself why
You shouldn’t be begging for forgiveness at my feet…
You should’ve said no, baby and you might still have me

[Verse 2]
You can see that I’ve been crying
And baby you know all the right things…to say
But do you honestly expect me to believe
We could ever be the same…
You say that the past is the past, you need one chance
It was a moment of weakness and you said yes…