"Not Pretty Enough" is a country song written by Kasey Chambers, produced by Nash Chambers for Chambers's second album Barricades & Brickwalls. It was released as the album's third single in the start of 2002 (see 2002 in music) in Australia as a CD single. It was a No. 1 hit in Australia the same year.

The song was written by Chambers as a commentary on the reluctance of commercial radio stations towards playing her music, despite her being an established performer. Ironically, the single prompted Chambers' commercial breakthrough, and was the song most added to radio station playlists in 2004.

In 2002, the song was used in the original un-aired pilot for Birds of Prey (TV series). It was replaced by the Oasis song Stop Crying Your Heart Out in the re-worked pilot that eventually aired.

In 2010, the song was used in the Australian horror film The Loved Ones to ironic effect as the sweet-sounding song is juxtaposed against the brutal, gore-filled violence. The song relates to the film's lead character, an unpopular girl who wonders why boys don't like her and who subsequently takes out her revenge on the object of her affection.

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