Songfacts®:

• The third single from Kasey Chambers' sophomore album Barricades & Brickwalls was a breakthrough hit in Australia for the singer-songwriter.
  
  When we interviewed Chambers in 2017, she explained what initially inspired the song. "I wrote it about not fitting into the music industry and feeling uncomfortable in such a superficial industry," she said. "Feeling like I would never fit into mainstream radio. Ironically, it became a radio hit in Australia on mainstream radio and went to #1 on the pop charts. I still resonate with the song today and have always done it over the years, but in many different ways. It has many different layers for me."
• The song has changed meaning for Chambers throughout the years: "'Not Pretty Enough' started out being about not fitting into the music industry, but is now more about just general insecurities that everyone feels at different times about different things," she said. "It has got me through a lot of things and I love knowing that it's helped other people through all the different times in their lives. That is the beauty of music."
  
  Chambers reiterated a similar thought in her interview with The Project. "More my anthem now than when I wrote it," she said. "When I wrote it, I was feeling really vulnerable about being part of an industry that was so superficial. I didn't really feel like I fit in very well. And listening to all the things that were successful on the radio at the time, Britney Spears, Shakira, Christina Aguilera, all of that. I was like, man, I do not fit in in this industry at all. I feel not pretty enough a lot, and that's where the song came from, really."
• Chambers performed this song with her longtime friend Keith Urban at the 2001 ARIAs (Australia's Grammys).