Anna Friel A Midsummer Nights Dream 1999 NSFW (1 photo)

Hilary Swank Boys Dont Cry 1999 NSFW

Renee Zellweger 1999 Pokies

Natalie Portman By Annie Leibovitz 1999 NSFW

Elizabeth Hurley 1999 The Spy Who Shagged Me Boobs

Amanda Redman As Diana Dors From The Tv Biopic The Blonde Bombshell 1999 NSFW

Jessica Alba From Idle Hands 1999 NSFW

Jaime Pressly Howard Rosenberg Photoshoot 1999 NSFW

Juliette Lewis From Strange Days 1999 NSFW

Monica Sweetheart Pornstar From 1999 2006 NSFW

Heather Kozar January 1998 Playmate Of The Month And 1999 Playmate Of The Year NSFW

Shannon Elizabeth American Pie 1999 NSFW

Lexus And Taylor Hayes House Of Sleeping Beauties 3 1999 NSFW

Rose Byrne In 1998 When Only Us Aussies Knew About Her Source Two Hands 1999 NSFW

Kimberly Spicer Playboy 1999 NSFW

Jaime Bergman Playboys Miss January 1999 And Bj Cummings From Son Of The Beach NSFW

Elizabeth Hurley Cfda Awards 1999 NSFW

Heidi Klum 1999 NSFW

Rena Mero Sable 1999 NSFW

Sable In 1999 For Playboy NSFW

Heidi Klum In In Bodypaint In The 1999 Si Swimsuit Edition NSFW

Nell Mcandrew Playboy 1999 NSFW

Naomi Campbell In Playboy 1999 NSFW

Charlize Theron Playboy May 1999 NSFW

Adriana Lima Marie Claire Italia May 1999 Ph Darren Keith NSFW (1 photo)

Mena Suvari In American Beauty 1999 NSFW (1 photo)

Scarlett Johansson In 1999 NSFW (1 photo)

Heidi Klum For The 1999 Sports Illustrated Issue NSFW (1 photo)

Thora Birch In American Beauty 1999 NSFW (1 photo)

Jennifer Aniston Topless Paparazzi Pics Taken In 1999 More Explanation In Comments NSFW (1 photo)

Charlize Theron For Playboy 1999 NSFW (1 photo)

Naomi Campbell Playboy December 1 1999 NSFW (1 photo)

Idle Hands 1999 Kelly Monaco As Tiffany NSFW (1 photo)