Ruminations on the pressure women face to stay thin, beautiful, and youthful have been a common thread in popular music for years, particularly because the pressure doesn’t seem to be going anywhere any time soon. Madonna told women to “Express Yourself.” Gwen Stefani stomped on the assumption that women are the weaker sex with her mosh-pit mainstay “Just a Girl.” And even Beyoncé had to work through the insecurity of “Pretty Hurts” before she could own the confidence of “Formation.”

In 1999, TLC tackled the topic of women’s self-worth with “Unpretty,” a meditation on how women are expected to transform themselves to meet unrealistic beauty standards. While a direct interpretation of the lyrics might suggest that the song seeks to free a woman from the oppression of trying too hard to please a boyfriend ("Never insecure until I met you"), the primary antagonist of this song is actually the woman herself.

I've tried different ways but it's all the same

At the end of the day I have myself to blame

“Unpretty” was the second single off TLC’s third studio album, Fanmail, and spent three weeks at No. 1 on the Billboard charts. Five years had passed since the release of their last album, the 11-time-platinum CrazySexyCool — the record that transformed Tionne "T-Boz" Watkins, Lisa "Left Eye" Lopes, and Rozonda "Chilli" Thomas from a girl group into seriously legit R & B thought divas.

Half a decade between albums is an extraordinarily long period of time for any group, especially one at the top of the charts. But the break wasn’t exactly a hiatus. TLC followed the multiplatinum success of CrazySexyCool by filing for Chapter 11 bankruptcy, a consequence of a shitty recording contract and an even shittier manager. Also during this time, Watkins revealed that she had been battling sickle cell anemia, and had recently been hospitalized. Thomas had a son with producer Dallas Austin, whom the group had just fired, then rehired. And Lopes burned down her boyfriend’s house, went to rehab, and announced she was going to record a solo album. The group’s breakup seemed imminent.

Instead, TLC was reborn with Fanmail, an album with grown-up themes about sex and relationships — peppered with enough profanity to earn the group its first Parental Advisory Label — and a hint of feminism, even though no one was calling it that yet. Singing about loving yourself the way that you are (the essence of “Unpretty”) or demanding higher standards from men (“No Scrubs”) stood in stark contrast to the underage boy-candy image of another newly minted pop star from that era: Britney Spears, who sparred with TLC on the charts that year.