"Tim McGraw" was released as the lead single from Taylor Swift on June 19, 2006. The song was critically appreciated for Swift's delivery. "Tim McGraw" enjoyed commercial success, peaking at number forty on the Billboard Hot 100 and at number six on Billboard's Hot Country Songs; it was certified platinum by the Recording Industry Association of America (RIAA) for the shipment of 2,000,000 copies.
"Teardrops on My Guitar" was released as the second single from Taylor Swift. "Teardrops on My Guitar" received critical success for its memorable chorus and crossover potential, as well as commercial success by becoming the best-charting single from Taylor Swift on the Billboard Hot 100, peaking at number thirteen. It became Swift's first pop crossover hit, peaking at number eleven on the now-canceled Pop 100 chart. The song was certified double platinum by the RIAA for the shipment of 3,000,000 copies."Teardrops on My Guitar" peaked at number forty-five in Canada and at number fifty-one in the United Kingdom.
"Our Song" was released as the third single from the album. The song was critically favored, being described as "gem". "Our Song" peaked at number sixteen on the BillboardHot 100 and was certified quadraple platinum by the RIAA; it also became Swift's first-number one on Hot Country Songs. The song peaked at number thirty on the Canadian Hot 100, becoming the best-charting single from Taylor Swift in Canada.
"Picture to Burn" was released as the fourth single from Taylor Swift. "Picture to Burn" was appreciated by contemporary critics for lyrics reflecting feminism. It became a fourth consecutive top ten single for Swift on the United States' chart Hot Country Songs and was certified double platinum by the RIAA.
"Should've Said No" was released as the fifth and final single from thealbum. In the United States, "Should've Said No" became Swift's second number-one on Hot Country Songs and was certified double platinum by the RIAA./The song made its highest international peak in the New Zealand Singles Chart, at number eighteen. As of December 2013, the best selling songs from the album are: Our Song 4,879,000; Teardrops on My Guitar 3,642,000; Picture to Burn 2,395,000; Tim McGraw 2,366,000; Should've Said No 2,255,000; I'm Only Me When I'm With You 2,174,000.
