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Welp, I went and did it. New designs for the 32 OO contestants (with new headcanons and all).
Close-ups:
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Marble, Lighter, Crayon, Melony and Snow Globe
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Toaster, Toothy, Fly Swat and Coney
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Candy, Globe and Tiki
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Paper Airplane, Top Hat, Pearly and Ping Pong Ball
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Cherry, Casey and Masky
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Picture, Kite, Tissue and Disc
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Boxing Glove, Soccer Ball, Dusty and Television
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Pumpkin, Popcorn, Clock, Boombox and Locky
Let me know what you think. (I'll probably make an OO book to showcase my headcanons.)