Look Back at the Biggest Stars of the 1999 Met Gala

Guests included '90s icons like Jennifer Love Hewitt and Christina Ricci and Whitney Houston and Bobby Brown.

By Corinne Heller May 04, 2019 10:00 AMTags
Whitney Houston, Met Gala 1999Rose Hartman/Getty Images

At the 1999 Met Gala, the stars were partying like it was...1999.

Guests included actress now considered '90s icons, such as Jennifer Love HewittChristina Ricci and Minnie Driver. Pop legend Whitney Houston, who died in 2012, attended the Met Gala with then-husband Bobby BrownJennifer Lopez arrived with then-boyfriend Sean "Diddy" CombsJerry Seinfeld brought along wife Jessica Seinfeld, two weeks before their wedding.

The 1999 Met Gala celebrated the launch of the Metropolitan Museum of Art's Costume Institute's "Rock Style" exhibition. There, guests Liv Tyler and designer Stella McCartney proved they are indeed rock royalty.

Things were different at the Met Gala in 1999. Simpler. Celebs did not dress as outrageously as they have at Met Galas in recent years. It was more glitz, more glam, less shock. The fashion was also, as it always is at the Met Gala, gorgeous.

The Most Controversial Met Gala Outfits Ever

See photos of stars at the 1999 Met Gala.

Minnie Driver

The actress is all smiles in sparkling silver.

Charlize Theron

The actress showcases a sparkling look.


The singer is all smiles in this printed dress.

Donatella Versace

The fashion designer actually debuted this dress a year before Jennifer Lopez made headlines with it at the 2000 Grammys.

Elizabeth Hurley

Liz channeled Angelina Jolie before that was a thing.

Jennifer Lopez and Sean "Diddy" Combs

The singer and actress and her then-boyfriend make it a date night.

Jerry Seinfeld and Jessica Seinfeld

The actor appears with his then-fiancé, then known as Jessica Sklar.

Christina Ricci

The Addams Family star channels Elsa.

Natasha Richardson and Liam Neeson

The actor appears with his wife, a decade before her death.

Gwyneth Paltrow

The Oscar winner was a brunette!

Kim Cattrall

The Sex and the City star puts the yin in the yang.

Milla Jovovich

The actress showcases a daring look.

Whitney Houston and Bobby Brown

The late singer and her-then husband make it a date night.

Anjelica Huston

The Addams Family star wows in a slinky silk dress.

Jennifer Love Hewitt

The '90s icon showcases a sexy angelic look.

Liv Tyler and Stella McCartney

Steven Tyler and Paul McCartney's daughters aren't wrong.

Lil' Kim

Pretty in pink!

Anna Wintour

Vogue's famous editor-in-chief appears with her signature sunglasses.

The 2019 Met Gala takes place on May 6.