"So Yesterday" was released as the lead single from the album on July 29, 2003. The song, written by Lauren Christy, Scott Spock, Graham Edwards and Charlie Midnight, was produced by production team The Matrix, who were notable at the time for their work with Avril Lavigne. Thus, some similarities arose between the song and the work of Lavigne. "So Yesterday" debuted on the "Billboard" Hot 100 chart at number fifty-three in the thirty-third week of 2003, and peaked at number forty-two in its eleventh week. It spent twenty weeks on the Hot 100. The song topped the US "Billboard" Hot 100 Singles Sales chart, making Duff the first artist in four months not affiliated with American Idol, to top the chart. The song peaked at number two in Canadian Singles Chart. In Australia the song debuted at number thirty-nine, peaked at number eight in its eighth week, and remained on the chart for twenty weeks. It was the forty-ninth best selling single of 2003 in Australia, and was certified platinum in 2004. In Japan, the song reached number 199 on the Oricon weekly charts. In United Kingdom, the song debuted at number nine on the UK Singles Chart. The song peaked in the top ten on the charts in other European countries such as the Netherlands and France. The Chris Applebaum-directed music video for the song premiered on MTV on July 24, 2003. It was later featured on MTV's "Making the Video" two days after the video's premiere on July 26, 2003. The video shows Duff playing a break-up prank on her aloof boyfriend.