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Kendra Wilkinson has led an eventful life. Since moving into Hugh Hefner’s home after she graduated high school as one of his live-in girlfriends, worked as a skin painting model and starred in sub-par reality TV shows. While living in the Playboy Mansion, Kendra starred in The Girls Next Door. May 14, 2016 · Once upon a time Kendra Wilkinson-Baskett and Holly Madison were roommates, chummily living the high life as two of Hugh Hefner's three main squeezes. The surreal party ended when Holly, and then Author: Natalie Finn.