Should've Said No

"Should've Said No" occupies track nine on the standard edition of Taylor Swift, the 2006 debut album that Big Machine Records released on October 24 of that year. Swift wrote the song alone, and by her own account the writing took about five minutes, in a studio bathroom. Nathan Chapman produced it. The arrangement sets banjo against distorted electric guitar, a combination that places the record somewhere between country rock and the stadium-sized pop rock Swift would lean into on later albums.

The lyric is a dressing-down delivered to a cheating ex, and it does not soften at the edges. Big Machine issued the track as the album's fifth and final single, sending it to US country radio on May 18, 2008, roughly nineteen months after the album itself had arrived. The delay did not hurt it. The song became Swift's second number one on Billboard's Hot Country Songs chart, reached number 33 on the Billboard Hot 100, and picked up a platinum certification from the RIAA for more than a million digital copies sold. It also charted in Canada and New Zealand.

For the official music video, Swift and her team used footage of her performance at the 43rd Academy of Country Music Awards rather than staging a separate shoot. The song stayed in her live sets for years afterward: it featured on the Fearless Tour (2009–2010), on her guest appearances during the Jonas Brothers' Burnin' Up Tour, and in a 2018 mashup with "Bad Blood" on the Reputation Stadium Tour. [edit]