In 1999, "Shakespeare in Love" won best picture and gave us Oscar's best actress (Gwyneth Paltrow) and best supporting actress (Judi Dench). James Coburn took home top honors for his supporting role in "Affliction" and Roberto Benigni won the best actor prize for his work in "Life is Beautiful." Also beautiful? The sea of gowns worn by Hollywood's finest. That show was 20 years ago, so Wonderwall.com is taking a look back at how these dresses stood the test of time, starting with the most famous look from the March 21 show: Gwyneth's baby pink Ralph Lauren gown that made her look like a princess as she won the best actress trophy. Keep reading for more…
Gothic-chic Oscar presenter Christina Ricci looked very serious at the 1999 show, which was held at the Dorothy Chandler Pavilion in Los Angeles, in a sparkly silver gown with intricate beading.
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Cate Blanchett, who was nominated for best actress for her performance in "Elizabeth" in 1999, choose a slinky black number with flower embellishments by John Galliano for her first walk down the world's most famous red carpet.
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Celine Dion's 1999 Academy Awards look has a permanent place on the Oscars worst dressed list. The "My Heart Will Go On" singer, who performed that night, chose a John Galliano for Christian Dior backward tuxedo and paired it with a white fedora and diamond-studded Ray Bans.
"When I wore that look, yes it was at the Oscars, and when I wore that, everyone was wearing dresses, not pants," Dion recalled in an interview with People in 2017. "I was the only one with pants in a backward suit from Galliano and if I would do this today it would work. It was avant-garde at the time. And it doesn't matter, you just have to assume what you wear, you wear, and I did."
Best original song performer Mariah Carey shared the stage with Whitney Houston for their track "When You Believe" from the animated movie "The Prince of Egypt" at the 1999 Academy Awards. Before performing, Mariah walked the red carpet for the first time in an unflattering white L'Wren Scott dress.
Uma Thurman, who presented the award for best cinematography, turned heads in a silver organza gown by Chanel. That year, she was not nominated for any Oscars but was nominated for two trophies at the competing Razzie Awards, which recognize the worst acting of the year, for her work in "The Avengers."
For her third time presenting at the Oscars, Jennifer Lopez choose a Badgley Mischka dress with rhinestone appliqués that, she admitted to Joan Rivers on the red carpet, was a departure from her standard sleeker looks.
The most Oscar-nominated actor of all time, Meryl Streep, walked the red carpet in 1999 as a best actress contender for her work in "One True Thing." While she lost out to Gwyneth Paltrow, her dress — a pale lavender Valentino gown — stunned.
Catherine Zeta-Jones might have only been at the Oscars to introduce a best song nominee, but she managed to steal the show with her curves in this red Versace number.
Two-time Oscar nominee Laura Dern walked the Academy Awards red carpet in 1999 with then-boyfriend Billy Bob Thornton, who was nominated for best supporting actor for his work in "A Simple Plan." While the relationship didn't last, the look did: Laura's dress would look great on any red carpet today.
Liv Tyler attended the 1999 Oscars to introduce "I Don't Want to Miss a Thing," the best song nominee from her movie "Armageddon" (her father, Steven Tyler, performed it with his band, Aerosmith). She walked the red carpet in a simple shimmery number that she could easily pull off today too — as long as she lost the wrap.
Lisa Kudrow, who attended the Oscars to introduce one of the best song nominees, wore a Randolph Duke ensemble that was figure-flattering but looking back, might have been too matronly for the "Friends" star.
Andie MacDowell, who presented the prize for best original musical or comedy score in 1999, wore an intricately beaded maroon and brown dress to the Oscars that year — a gown that would still look beautiful on any red carpet in 2019.
Anjelica Huston, who became the third person in her family to win an Oscar 13 years before the 1999 show, walked the red carpet with late husband Robert Graham in a conservative sparkly frock before she presented the award for best sound.
Laura Linney's 1999 Oscar dress has not survived the test of time, as the then-35-year-old's ensemble now looks like something a woman twice her age would wear!
Helen Hunt, who won an Academy Award in 1998 for her work in "As Good As it Gets," choose a stunning Gucci dress for her return to the Oscars red carpet. While the gown was a great choice, it seemed like the best actor presenter could have used an extra round of tailoring.
When it's your night, you go big, and Rachel Griffiths' Richard Tyler gown did the trick. The best supporting actress nominee for "Hilary and Jackie" chose a loud iridescent pink dress with matching gloves that were the definition of extra.
Geena Davis, who presented the award for best original dramatic score, looked positively angelic in a ballgown by Bradley Bayou that required five fittings.
Twenty years ago, Tom hanks was nominated for best actor for his performance in "Saving Private Ryan." He didn't win, but he took home something else sparkly and shiny: wife Rita Wilson in a figure-flattering sparkly silver gown.
Judi Dench — who won the Oscar for best supporting actress for her eight-minute role in "Shakespeare in Love" in 1999 (her only win over seven nominations) — chose a dress and coat by Abu Jani-Sandeep for her big night.
Best supporting actress nominee Lynn Redgrave (for "Gods and Monsters") wore Amsale on the Oscars red carpet and won the support of snarky fashion critic Joan Rivers. "I loved the color, the sophistication," Joan said.