The Many Loves Of Hugh Hefner, The Luckiest Bastard In The World

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Picture 13 of 30
Picture 13 of 30

Kendra Wilkinson
The Sporty Spice of The Girls Next Door, Kendra always struck us as the softball pitcher from your high school who made a few small mistakes after graduation. After Girls Kendra did some serious trading up, marrying slamming hot NFL player Hank Baskett and giving birth to adorable baby boy Hank in December 2009. In 2010, she enjoyed a short run of her reality show Kendra, published a memoir and leaked a sex tape to the press. Given that the tape does not also star Hefner, we'd say she's had a red-letter year so far. [Photo: WireImage]

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