Playboy Jan 1999
Playboy's Lingerie # 65 - January/February 1999
FeaturesCovergirl Brooke Richards, Karin Taylor, Victoria Zdrok, Alley Baggett, Alesha Oreskovich and Lisa Marie Scott Photographed by Andrew GoldmanSung Hi LeePatricia FordJoy Behrman
Playboy's Girls of Winter # 3 (1999)
FeaturesCovergirl Kelly Monaco and Stephanie Wood Photographed by Gen NishinoJessica HumphriesKelly PrestonChristina Steffer
Playboy Feb 1999
Playboy's Real Sex # 2 (1999)
FeaturesCovergirl Rosie Ciavolino Photographed by Gen NishinoChristina SmithCarlee BenoitBridgett Wise
Playboy's Playmates in Bed # 3 (1999)
FeaturesCovergirl Carrie Stevens Photographed by Kim MizunoLynn ThomasVictoria SilvstedtNadine Chanz
Playboy Mar 1999
Playboy's College Girls # 9 (1999)
FeaturesCovergirl Sheila Bell Photographed by Andrew GoldmanStephanie LeannAdina ReedBrandy Marie
Playboy's Lingerie # 66 - March/April 1999
FeaturesCovergirl Katalina Verdin Photographed by David RamsMelissa ReigelStephanie WoodBebe Buell
Playboy Apr 1999
Playboy's Sexy Girls Next Door # 2 (1999)
FeaturesCovergirl Julia Brox Photographed by George GeorgiouMarlena BowmanNatasha YiEvonne Mills
Playboy's Celebrating Centerfolds Vol. 2
FeaturesCovergirl Karen McDougal Photographed by Kim MizunoAva FabianVicki WittDebra Peterson
Playboy May 1999
Playboy's Natural Beauties # 2 (1999)
FeaturesCovergirl Lisa Marie Scott Photographed by Andrew GoldmanSoli MariaElisa BridgesAlicia Williams
Playboy's Lingerie # 67 - May/June 1999
FeaturesCovergirl Victoria Silvstedt Photographed by MizunoCourtney ReedJoy BehrmanNikki Schieler
Playboy Jun 1999
Playboy's Girls of Summer # 15 (1999)
FeaturesTiffany BuecherKorina NakidaPatricia FordBianca Lucia
Playboy's Playmate Tests # 2 (1999)
FeaturesCovergirl Alesha Oreskovich Photographed by Cynthia KayeCarrie WestcottShae MarksDebra Jo Fondren
Playboy Jul 1999
Playboy's Hardbodies # 2 (1999)
FeaturesCovergirl Haven Gaston Photographed by Cynthia KayeCarla McFarlanMykell MartinCheryl White
Playboy's Lingerie # 68 - July/August 1999
FeaturesCovergirl Christi Taylor Photographed by Phillip VulloKatalina VerdinTara KingMonica Mesones
Playboy Aug 1999
Playboy's Sex Stars of the Century (1999)
FeaturesCovergirl Pamela Anderson and Cindy Crawford Photographed by Stephen Wayda and Herb RittsJenny McCarthyAnna Nicole SmithKatarina Witt
Playboy's Playmate Review # 15 (1999)
FeaturesCovergirl Heather Kozar Photographed by MizunoVanessa GleasonLaura CoverTiffany Taylor
Playboy Sep 1999
Playboy's Girlfriends # 2 (1999)
FeaturesCovergirl Milan Nalina and Baby Norman Photographed by Troy PlotaKelly MonacoSydney MoonCheryl Stell
Playboy's Lingerie # 69, September/October 1999
FeaturesCovergirl Tiffany TaylorHeather KozarLisa Marie ScottJoy Behrman
Playboy's Voluptuous Vixens # 3 (1999)
FeaturesCovergirl Robin Arcuri Photographed by Andrew GoldmanNadine ChanzStacy SanchesTiffany Taylor
Playboy's Celebrating Centerfolds Vol. 3
FeaturesCovergirl Layla Roberts Photographed by MizunoDianne DanfordLisa DerganDinah Willis
Playboy Nov 1999
Playboy's Wrestling Superstar Sable (1999)
FeaturesCovergirl & Centerfold Rena Mero Photographed by Arny FreytagQ&ADear DiaryRetro Rena
Playboy's Lingerie # 70 - November/December 1999
FeaturesCovergirl Angela Little Photographed by Kim MizunoVictoria SweetMonica MesonesJulia Brox
Playboy Dec 1999
Playboy's Nudes # 10 (1999)
FeaturesCovergirl Sung Hi Lee Photographed by MizunoHeather KozarBrandee SkyLynn Thomas
Playboy's Barefoot Beauties # 1 (1999)
FeaturesCovergirl Mysti Sherwood Photographed by George GeorgiouTeresa TooleVanessa GleasonIleana Romero
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