“Should’ve Said No” is performed by American country pop singer Taylor Swift and taken from her self-titled debut album. It was released on 19 May, 2008 by Big Machine Records as the fifth single from the album. It was produced by Nathan Chapman and written by Taylor Swift. It was certified platinum by the Recording Industry Association of America (RIAA).
Chris Neal from Country Weekly said about “Should’ve Said No” that “the song with previous single ‘Picture to Burn‘ are the best songs from her debut album”. Roger Holland from PopMatter commented “Superb country arrangement made the pop-rock song splendid”. Alison Bonargur from the Chicago Tribune said “Invisible and revenge song”.
“Should’ve Said No” ranked at number 1 on the Billboard Country Songs Chart, at number 33 on the Billboard Hot 100 Chart, at number 18 on the RIANZ Singles Chart and at number 67 on the Canadian Hot 100 Chart.