A fresh-faced Pamela Anderson when she was Miss February 1990 for Playboy. We love Pam in all of her incarnations but it’s fun to remember when she looked so damned sweet and innocent. Who knew she would rule the next two decades?

A fresh-faced Pamela Anderson when she was Miss February 1990 for Playboy. We love Pam in all of her incarnations but it’s fun to remember when she looked so damned sweet and innocent. Who knew she would rule the next two decades?

Jenna Jameson And Her Very Sexy Shadow.

Dian Parkinson Graced The Pages Of Playboy Back In May 1993 After She Accused Game Show Host Bob Barker Of Sexual Harassment On The Set Of The Price Is Right. The Blonde Beauty Won The Miss District Of Columbia Usa Title And Competed As Diana Batts

Nice Nails, Dian Parkinson.

Jana Defi Doesn&Amp;Rsquo;T Want To Be Alone Right Now.

Tessa Fowler Gives Good Profile &Amp;Ndash; Or Some Unnecessary Photoshop?

Playmate Of The Month June 1997 Carrie Stevens Killing It With The Brunette Hair And Light Blue Eyes.

Dolly Parton Graced The Cover But Only Revealed Herself In The Playboy Interview And Not In The Centerfield, Sadly. Oh, What Could Have Been But We At Least Have This Delightful And Promising Cover Pic.

Heather Graham Being All Perfect In Boogie Nights. The Director Offered The Role To Gwyneth Paltrow But She Couldn&Amp;Rsquo;T Deal With The Enthusiastic Nudity. Her Loss And History’s Gain.

A Rather Glam Heather Graham - They, That Almost Rhymes - Checks Out The Celeb Rags On A Saturday Night.

One Of The Iconic Image Of Playboy From The Big80S - Supermodel And All Around Nice Person Cindy Crawford Performs Her Handbra In The July 1988 Edition. Photographed By Herb Ritts, If I Recall. So These Shots Are More Arty Than Smutty, Right?

Great, Now I Want A Sugar-Covered Cruller - Thanks, Cindy Crawford And Herb Ritts.

Tessa Fowler Putting On Her Bra - This Should Be A Sad Moment But We Know She Will Only Look Hotter.

TBoIRule34 TGirlPoV