1990-2009

This list has 36335 items

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Playboy's Cheerleaders
IMDb: tt0215612 TMDb: 1177296
Playboy's Cheerleaders
Playboy's Club Lingerie
IMDb: tt0232421 TMDb: 922590
Playboy's Club Lingerie
Playboy's Erotic Fantasies
IMDb: tt0105149 TMDb: 445310
Playboy's Erotic Fantasies
Playboy's Erotic Fantasies III
IMDb: tt0414964 TMDb: 445313
Playboy's Erotic Fantasies III
Playboy's Erotic Fantasies IV, Forbidden Liaisons
IMDb: tt0172996 TMDb: 804093
Playboy's Erotic Fantasies IV, Forbidden Liaisons
Playboy's Fast Women
IMDb: tt0348608 TMDb: 1630948
Playboy's Fast Women
Playboy's Freshman Class
IMDb: tt0215781 TMDb: 1177306
Playboy's Freshman Class
Playboy's Girlfriends 2
IMDb: tt0286896 TMDb: 961960
Playboy's Girlfriends 2
Playboy's Naturals
IMDb: tt0155958 TMDb: 398749
Playboy's Naturals
Playboy's No Boys Allowed 2
IMDb: tt0471323 TMDb: 925330
Playboy's No Boys Allowed 2
Playboy's No Boys Allowed 4: Naughty and Nice
IMDb: tt1057970 TMDb: 845045
Playboy's No Boys Allowed 4: Naughty and Nice
Playboy's Playmate Bloopers
IMDb: tt0471324 TMDb: 1714396
Playboy's Playmate Bloopers
Playboy's Playmates Bustin' Out
IMDb: tt0368928 TMDb: 1249309
Playboy's Playmates Bustin' Out
Playboy's Sexy Girls Next Door
IMDb: tt0466096 TMDb: 1281896
Playboy's Sexy Girls Next Door
Playboy's Sisters
IMDb: tt0248440 TMDb: 1144514
Playboy's Sisters
Playboy's Tales of Erotic Fantasies
IMDb: tt0216263 TMDb: 639067
Playboy's Tales of Erotic Fantasies
Playboy's Voluptuous Vixens II
IMDb: tt0152000 TMDb: 5706
Playboy's Voluptuous Vixens II
Playboy's WildWebGirls.com
IMDb: tt0201847 TMDb: 1559566
Playboy's WildWebGirls.com
Playboy's: Erotic Underground
IMDb: tt0289939 TMDb: 458281
Playboy's: Erotic Underground
Playboy: Biker Babes, Hot Wheels & High Heels
IMDb: tt0215567 TMDb: 1167691
Playboy: Biker Babes, Hot Wheels & High Heels
Playboy: Blue Collar Babes
IMDb: tt0260284 TMDb: 1390106
Playboy: Blue Collar Babes
Playboy: Cyber Girls
IMDb: tt0352724 TMDb: 149162
Playboy: Cyber Girls
Playboy: Erotic Fantasies II
IMDb: tt0330261 TMDb: 333927
Playboy: Erotic Fantasies II
Playboy: Girls Down Under
IMDb: tt0272107 TMDb: 1249263
Playboy: Girls Down Under
Playboy: Girls of South Beach
IMDb: tt0304558 TMDb: 760521
Playboy: Girls of South Beach
Playboy: Girls of the Hard Rock, Hotel & Casino Las Vegas
IMDb: tt0313483 TMDb: 1177823
Playboy: Girls of the Hard Rock, Hotel & Casino Las Vegas
Playboy: Girls of the Internet
IMDb: tt0216094 TMDb: 731839
Playboy: Girls of the Internet
Playboy: Hot City Girls
IMDb: tt0304559 TMDb: 1249279
Playboy: Hot City Girls
Playboy: Hottest Housewives
IMDb: tt0473525 TMDb: 736367
Playboy: Hottest Housewives
Playboy: Inside the Sexy Girls Next Door House
IMDb: tt0471319 TMDb: 1105752
Playboy: Inside the Sexy Girls Next Door House
Playboy: Love, Sex & Intimacy... for New Relationships
IMDb: tt0471321 TMDb: 941415
Playboy: Love, Sex & Intimacy... for New Relationships
Playboy: Playmates Revisited
IMDb: tt0216097 TMDb: 1622701
Playboy: Playmates Revisited
Playboy: Playmates Unwrapped
IMDb: tt0466095 TMDb: 799406
Playboy: Playmates Unwrapped
Playboy: Playmates at Play
IMDb: tt0100372 TMDb: 569655
Playboy: Playmates at Play
Playboy: Playmates in Bed
IMDb: tt0353887 TMDb: 1144336
Playboy: Playmates in Bed
Playboy: Playmates on the Catwalk
IMDb: tt0352719 TMDb: 1249313
Playboy: Playmates on the Catwalk