Playboy Playmates 1999 Playmate of the Year: Heather Kozar Miss January: Jamie Bergman Miss February: Stacy Fuson Miss March: Alexandria Karlsen Miss April: Natalia Sokolova Miss May: Tishara Lee Cousino Miss June: Kimberly Spicer Miss July: Jennifer Rovero Miss August: Rebecca Scott Miss September: Kristi Cline Miss October: Jodi Ann Paterson Miss November: Cara Wakelin Miss December: Brooke Richards
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