"Why Can't I?" is the first single from Liz Phair's 2003 self-titled album, Liz Phair. It reached number 32 on the Billboard Hot 100, Phair's highest-charting single to date.
The B-sides are "Jeremy Engle" and "Fine Again".
The song was featured in the films How to Deal, 13 Going on 30, and Win a Date with Tad Hamilton! It was also featured in the television series The O.C. and in the tenth season promo for Friends.
The video was directed by Phil Harder. Released in January 2004, it is remembered for all the looks Phair had. It shows a person, presumably Phair, playing the song on a jukebox. If you look closely at the CD it is playing, it is the Liz Phair album. She pushes buttons on the box throughout the video. The whole rest of the video consists of Phair and her band performing in various colors that resemble CD covers, which are named after the song's lyrics. For example, one title is "Why can't I speak or breathe," which is derived from the chorus. In this regard, this video is similar to a music video created in 2005 for "Nth Degree" by the band Morningwood,.