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Playboy November 1999
Playmate of the Month
Cara Wakelin photographed by Richard Fegley.

Jesse Ventura by Lawrence Grobel.
Sheryl Crow by Mark Ribowsky.

David Duval by Carl Vigeland.

20 Questions
George Jones.

"Playboy's History of the Sexual Revolution -- Part X (1990-1999): Real Sex" by James R. Petersen.

Sex in Cinema 1999
Tom Cruise and Nicole Kidman, Scott Carson and Maria Ford, Anna Kaminskaia and Susan Featherly, Cristian Bale and Emily Watson, Jeannie Pepper and Lexington Steele, Shannon Elizabeth (not nude), Jason Biggs (not nude), Nina Hoss (slutty pose, not nude), Chris Stafford and Tina Holmes (under sheets), Karyn Dwyer and Christina Cox (under sheets), Gwen Somers (with a female), Shyra DeLand Chase Conville and Brad Bartam (threesome), Claudia Schiffer and Robert Downey Jr. (seductive scene, not nude), Alison Eastwood and Neill Bary, Suzanne Cryer and George Newbern, Julia Roberts and Hugh Grant (covered by sheets), Sophie Marceau and Pierce Brosnan (not nude), Diane Lane and Viggo Mortensen (seductive, his back exposed), Kate Winslet (breast exposed), Sergio Assisi and Gabriella Pession, Rocco Siffredi and Caroline Ducey, Natacha Regnier and Gregoire Colin.

Mia St. John (cover) photographed by Arny Freytag.

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