@erect-eggplant posted a screenshot that included these two, and I could NOT get this idea out of my head.
They have that despondent disinterested look of bored rich white kids so prevalent in 90's and 00's fashion advertising.
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Hilary Duff in 00′s photoshoot.
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Brandy Norwood
Simply known as Brandy, she was one of the most popular R&B artists of the 90s and is known for her distinctive sound, characterized by her peculiar timbre, voice-layering, and intricate riffs, which has earned her the title of "the Vocal Bible".
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Mariah Carey at the Music Visionary of The Year Awards (2003)
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Chilli in Season 5, Episode 22 of 'That 70s Show' (2003).
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