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Playboy December 1999
Gala Christmas Issue

Playmate of the Month
Brooke Richards photographed by Stephen Wayda.

Ben Affleck by Bernard Weinraub.

20 Questions
Gina Gershon by Robert Crane.

"Bill Clinton's Life Lessons" by Christopher Buckley.
"A Decade of Scream Queens" by Robert B. DeSalvo.
"Tribute to Shel Silverstein" by Jules Feifer.
"City Girls" by Amy Sohn.
"Playboy's College Basketball Preview" by Gary Cole.
"The Duke (Ellington)" by Wynton Marsalis.
"Gulf War II" by Scott Ritter.

Naomi Campbell (cover and inside, totally nude) photographed by David Lachapelle.

Sex Stars 1999
Ricky Martin, Jennifer Lopez, Catherine Zeta-Jones, Elizabeth Hurley, Sophie Marceau, Hugh Grant, Shania Twain, Julia Roberts, Keri Russell, Heather Kozar, Denis Richard, Rene Russo, Rebecca Romijn-Stamos, Cameron Diaz, Laetitia Casta, Nikki Schieler, Caprice, Tom Cruise, Nicole Kidman, Pamela Anderson, Pierce Brosnan, Mia St. John, Angelina Jolie, Halle Berry, Sean Connery, Nell McAndrew, Charlize Theron, Will Smith, Heather Graham and Rena Mero (some previously named are nude).

Playboy 200 Playmate Search
Megan McKenney photographed by David Chan, Jamie and Julie Jordan, Julia Seidelin, Twila Young, Laura Han, Katherine Zarria, Joei Harlow, Samantha Speer, Feather Frazier, Shelley Lane, Bridget Shaw, Samantha Corder, Jessica Jurkowski, Kristina Sanchez photographed by Bill White, Nicole Lenz, Amanda Callan, Tara Flether, Sara Steele, Suzanne Stokes, Flo Wu, Casey Ross, Jennifer Corliss, Polly Belleville, Barbara Adi, Jessica Tindall, Jill Manas, Kimberly Burkhead, Aubrie Lemon, Leanne Burns, Carla Alapont, Darlene and Carol Bernaola, Sonia Flores, Wendy Rosprim, Merritt Cabal, Katie Lohmann, Katie Hammers, Melissa Keil, Mikki Chernoff, Nancy Lesco, Amy and Angela Overton, Jackie Currier, Katia Corriveau, Sasha Peralto, Jana Rehackova, Jaimie Chiaravalle, Angi Pyne photographed by Bill White, Laura Lee, Miriam Gonzales, Regina Usvjat, Crystal Beddows, Annie Proulx, Sharon Wilson, Ashlee Miller.

Adults Only
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Adults Only
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