Big Machine Records announced the release of "Should've Said No" on Monday, May 19. The song is the fifth and final single from Swift's debut album. She performed it on the 43rd Annual Academy of Country Music Awards. The performance started off with her dressed in a hooded sweatshirt and jeans, but soon after a short black halter dress was revealed. In the last minute of the song, she went backstage to perform the final verse under a cascading waterfall. Swift had wanted to do that performance on stage with the water and the change of clothes since she was ten years old. "Should've Said No" became her second Number One single for the chart dated August 23, 2008.