"Should've Said No" is a song written and recorded by American singer-songwriter Taylor Swift for her self-titled debut studio album (2006). The song was released to US country radio as the album's fifth and final single on May 19, 2008, by Big Machine Records. Produced by Nathan Chapman, "Should've Said No" combines country rock, pop rock, and post-grunge with banjo and distorted guitars. The lyrics are about Swift's contempt for a cheating ex-lover. the demo was also recorded in 2004.
Music critics praised the song's production and Swift's songwriting. "Should've Said No" was Swift's second number-one single on the Hot Country Songs chart and peaked at number 33 on the Billboard Hot 100. The single was certified platinum, for exceeding one million digital copies sold, by the Recording Industry Association of America (RIAA). It entered the singles charts in Canada and New Zealand.
Swift performed "Should've Said No" live at the 43rd Academy of Country Music Awards; the performance was recorded and released as the official music video. The song was also included in the set list of her first headlining tour, the Fearless Tour (2009–2010). She also sang the song as a guest star on the Jonas Brothers' Burnin' Up Tour; the performance was featured in the concert film Jonas Brothers: The 3D Concert Experience. In 2018, she included a mashup of "Should've Said No" and "Bad Blood" in the set list of her Reputation Stadium Tour.
"Should've Said No" was a last-minute addition to Taylor Swift's 2006 self-titled debut studio album; she wrote it two days before the album was mastered and published and completed the track with producer Nathan Chapman overnight.[1][2] She said she wrote it as a reaction to something "dramatic and crazy" that happened to her, and she felt that she needed "to address it in the form of music".[1] The first line that came to her was the title, and she wrote the refrain in five minutes. Swift said that many of the lyrics were based on actual words that she used when confronting her ex-boyfriend.[2] The whole song took her 20 minutes to compose.[3] Swift commented that "Should've Said No" and "Picture to Burn" are the two songs on the album that depict a vengeful attitude towards those who wronged her;[2] whereas "Picture to Burn" has an angry 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."[3]
"Should've Said No" is an uptempo country rock song[4][5][6] that incorporates a banjo and opens with a steel guitar riff.[7][8] Roger Holland of PopMatters categorized the track as pop rock and said that the country-music arrangement was minimal.[9] Brittany Spanos from Rolling Stone remarked that "Should've Said No" stands out as a pop-rock-leaning tune in a country-music album.[10] In The Guardian, Alexis Petridis described it as a "post-grunge stadium rock anthem".[11] Musicologist James E. Perone commented that "Should've Said No" features a production incorporating textured guitars that resembles a rock power ballad, and includes elements of American folk music through the use of the pentatonic scale in the melody and the fiddles in unison with other instruments.[12]