1. Pamela Anderson, February 1991
2. Stephanie Seymour, March 1991
3. Corinna Harney, June 1992
What she's up to now: Corinna is an accomplished actor and producer, starring in such notable film and television hits as Nash Bridges, CSI: Crime Scene Investigation, Rat Race, National Lampoon's Vegas Vacation, and Yonkers Joe.
4. Erika Eleniak, December 1993
5. Elle Macpherson, May 1994
What she's up to now: Elle Macpherson has worn many hats in her life: model, actor, entrepreneur — but her most dedicated work seems to lie in philanthropy. In 2007 she partnered with Naomi Campbell to raise money and awareness for the victims of Britain's disastrous flooding, and even offered to cast her nude body so it could be auctioned off for charity.
6. Cindy Crawford, May 1996
7. Donna D'Errico, November 1996
8. Jenny McCarthy, December 1996
9. Claudia Schiffer, May 1997
What she's up to now: Claudia is currently the creative director of her very own brand, Claudia Schiffer Cashmere, and makes time in between her busy schedule to work on behalf of UNICEF. She is both a member of the organization's Arts & Entertainment Support Committee and a U.K. Goodwill Ambassador.
10. Victoria Silvstedt, June 1997
11. Shannon Tweed, January 1998
12. Traci Bingham, June 1998
What she's up to now: Since modeling for Playboy, Traci has gone on to appear in numerous films and television shows, most notably appearing alongside her former Baywatch co-star in Comedy Central's Roast of David Hasselhoff. Bingham is also a staunch vegetarian, and hosts a morning radio broadcast on WAAF in Boston.
13. Karen McDougal, July 1998
What she's up to now: Karen has hosted an array of reality television shows such as Wild On! on E! and The Red Carpet on Showtime, and appeared in several big-budget films including Joe Dirt, Charlie's Angels, The Girl Next Door, and Raising Helen. She was also voted the second sexiest '90s Playmate of all time by Playboy readers in 2001.
14. Julie Brown, August 1998
What she's up to now: "Downtown" Julie Brown, as she's come to be known over the years, has appeared in a slew of films and television shows, which include Spy Hard; The Weird Al Show; B*A*P*S; Walker, Texas Ranger; I'm a Celebrity, Get Me Out of Here!; and RuPaul's Drag U. Her most recent television credit, however, was on ABC's Wife Swap in 2013. She now hosts "The Back in The Day Replay Countdown" radio show on SiriusXM.
15. Naomi Campbell, December 1999
What she's up to now: Campbell continues to be an outspoken critic of the fashion industry, citing racial discrimination from her days on the catwalk. Campbell later established two charities; her first, We Love Brazil, aimed to raise awareness and combat the country's economic woes, and her second, Fashion for Relief, sought to raise funds for the victims of Hurricane Katrina, the India terrorist attacks of 2009, the Haiti earthquake of 2010, and the Japan earthquake of 2011. In 2011, the latter helped raise over £4.5 million.