1. Then: Judit Mascó (1990)
This cover helped launch the international career of the then 20-year-old Spanish model.
Judit continued modeling throughout the 1990s and still appears occasionally in fashion spreads and ad campaigns. She has also branched into television and writing, her memoir, El Libro de Judit Mascó (Judit Mascó’s book), was published in 2003.
3. Then: Ashley (Richardson) Montana (1991)
Ashley was a well established model when she appeared on the cover; she had already appeared on the cover of Elle seven times and on the cover of Cosmopolitan twice.
4. Now: ?
Aside from her cover, Ashley made five other appearances in the Sports Illustrated Swimsuit Issue (1989, 1990, 1992, 1993, and 1995). Since the late ’90s she has kept a low profile.
5. Then: Kathy Ireland (1992)
This was Kathy’s second cover. Her first cover was the 1989, best-selling, 25th anniversary issue.
Kathy was featured for 13 consecutive years in the Sports Illustrated Swimsuit Issue. Today she is CEO and chief designer of her own brand product marketing company, Kathy Ireland Worldwide. The company produces a wide range of products including furniture, lighting, jewelry, and clothing.
7. Then: Vendela Kirsebom (1993)
The Norwegian-Swedish model landed the cover at age 26.
Today (pictured here in 2010), she continues to occasionally model, as well as hosting international editions of Top Model. She also acts as goodwill ambassador for UNICEF.
9. Then: Elle Macpherson, and Rachel Hunter (1994)
Elle became the first and only four-time cover model, having appeared previously on the cover in 1986, 1987, and 1988.
This was Rachel’s first appearance on the cover and she was actually pregnant at the time with her second child (with then-husband Rod Stewart).
Elle moved into acting in the ‘90s, most memorably appearing as Janine LaCroix on Friends. Currently, she is the host of Britain & Ireland’s Next Top Model.
Today, she is currently a judge on New Zealand’s Got Talent.
12. Then: Daniela Pestova (1995)
This was the first cover for the then 24-year-old Czech model.
Daniela continued modeling throughout the 2000s, even appearing on the 2000 and 2006 covers of Sports Illustrated Swimsuit Issue. Today, she keeps a relatively low profile.
14. Then: Valeria Mazza (1996)
The then 24 year-old Argentine model shared a cover with Tyra Banks, who was first African-American cover model.
Valeria retired from modeling in 1998, choosing to focus on raising a family.
16. Then: Tyra Banks (1997)
In 1997, Tyra became the first and only African-American solo cover model (in 2007 Beyoncé shared her cover with Bar Refaeli in an inset).
Tyra (seen her “smizing”) continues to host America’s Next Top Model, which recently wrapped it’s 19th season.
18. Then: Heidi Klum (1998)
The cover that launched Heidi into international stardom.
Today, Heidi is best known as the host, judge, and executive producer of Project Runway.
20. Then: Rebecca Romijn (1999)
This was Rebecca’s first cover (she would appear again in 2006).
Today, Rebecca is best known for her role as Mystique in the X-Men films, and for her role as Alexis Meade on the television show Ugly Betty. She currently appears as Jessie, on Adult Swim’s NTSF:SD:SUV::.