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--Curmudgeon Sara Jean Underwood (born March 26, 1984) is an American model who was chosen as the Playmate of the Month for the July 2006 issue of Playboy magazine and later became Playmate of the Year in 2007. Sara Jean Underwood is an American model, television host, and actress, best known for being chosen as the Playmate of the Month for the July 2006 issue of Playboy magazine and later becoming Playmate of the Year in 2007. 03916 between 1-10 (based on their top 20 pictures) AZNude has a global mission to organize celebrity nudity from television and make it universally free, accessible, and usable. May 21, 2024 · Sara Jean Underwood is an American model, television host, and actress, best known for being chosen as the Playmate of the Month for the July 2006 issue of Playboy magazine and later becoming Playmate of the Year in 2007. 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