1. Pamela Anderson, February 1991
2. Stephanie Seymour, March 1991
4. Erika Eleniak, December 1993
What she's up to now: Erika joined the fourth season of the VH1 reality show Celebrity Fit Club back in 2006. Since then, she's managed to stay under the radar, but has done numerous guest appearances on network TV.
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
What she's up to now: Cindy Crawford has focused a great deal of her post-modeling attention on charitable causes. In 2007 she became an official member of the Ronald McDonald House Charities celebrity board (Friends of the RMHC), and serves on the California Wildlife Center's Honorary Committee.
7. Donna D'Errico, November 1996
What she's up to now: Donna fulfilled one of her lifelong dreams by climbing Mount Ararat in 2012. She even made a documentary about her experience, which she financed on Kickstarter.
8. Jenny McCarthy, December 1996
What she's up to now: Jenny McCarthy is perhaps best known for her anti-vaccination campaign that resurfaced in the '00s. While her stint on The View only lasted one season, she is now the host of Dirty, Sexy, Funny with Jenny McCarthy on SiriusXM.
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
What she's up to now: Victoria has had a very lucrative modeling career through the years which, even at the age of 40, hasn't slowed down. She even released an autobiography, titled Les Secrets de Victoria, in France in 2010.
11. Shannon Tweed, January 1998
What she's up to now: While Shannon was living in the Playboy mansion she met the future love of her life, KISS frontman Gene Simmons. She was eventually featured on the A&E reality show Gene Simmons Family Jewels, and after 28 years together, they tied the knot in 2011.
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.