“Why Can’t I?” is the lead single from Liz Phair’s self-titled studio album. The lyrics find Phair chronicling a doomed but passionate relationship with a man who’s already spoken for.

The song marked a stylistic departure for Phair, with her swapping laid-back production and acoustic guitars for of-the-time pop-rock instrumentation. The song was produced by The Matrix, the noughties production powerhouse best known for their work on songs by Avril Lavigne and Hillary Duff.

In 2003, the song peaked at #32 on the Billboard Hot 100 and #7 on Billboard’s Hot Adult Top 40 chart, becoming Phair’s biggest hit to date. Despite its commercial success, however, the single – like the album which spawned it – was panned by critics, who deemed her pop-rock crossover unwise and the lyrics to be “cookie-cutter.”