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"Unpretty" originated from a poem of the same name written by TLC member Tionne "T-boz" Watkins, which dealt with a woman's struggle with her self-image. The poem also addressed the comparisons many people make between themselves and the sometimes unrealistic concepts of beauty, as it is commonly portrayed in the media. Upon reading the poem, TLC producer Dallas Austin helped Watkins adapt the poem into a song, which TLC recorded as an empowering song for their fan base to overcome feelings of physical inadequacy. Watkins and Rozonda "Chilli" Thomas sing lead on the song, with backing vocals by Watkins and Debra Killings. A remixed version, sampling Dennis Edwards & Siedah Garrett's "Don't Look Any Further", was produced by JayDee of 1208Ent. & "Mad" Mike Lewin. Some versions of the remix feature a rap by TLC member Lisa "Left-Eye" Lopes. "Unpretty" was later covered by La Musique Populaire for their 2004 boxed set A Century of Song.
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