The Most Epically '90s Vintage Photos from the “Vanity Fair” Oscar Party
The Most Epically '90s Vintage Photos from the “Vanity Fair” Oscar Party
Alex ApatoffSun, March 15, 2026 at 5:00 PM UTC
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Credit: Jeff Kravitz/FilmMagic; Vinnie Zuffante/Getty; Jim Smeal/Ron Galella Collection via Getty
The Vanity Fair Oscar party has become almost more of a destination than the Oscars red carpet itself, with massive stars arriving at their appointed time to mix and mingle with their friends, marvel over the wardrobe changes and cheer for the night's big winners. The fashion is major, the red carpet is intense and the photos are legendary.
But its origin story was a bit more humble: Editor-in-chief Graydon Carter decided to try a small party at Mortons in L.A. for a mix of influential people and Academy Awards attendees. According to the oral history of the party, it was an instant hit — not least of all because it was an exclusive night when stars could really let their hair down without cameras around.
These days, there's always a camera right around the corner, and the vibes have shifted somewhat. So let's revisit the incredibly '90s moments (the midriffs! The iridescent gowns! The over-the-top updos!) with these spectacular throwbacks from the early days of the Vanity Fair Oscar party.
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Janet Jackson
Credit: Jeff Kravitz/FilmMagic
Janet Jackson bared her famous abs at the 1999 party.
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Claudia Schiffer & David Copperfield
Credit: Ron Galella/Ron Galella Collection via Getty
Claudia Schiffer and David Copperfield were still making magic at the 1994 event.
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Julianne Moore
Credit: Hulton Archive/Getty
Julianne Moore told a shorts story in 1995.
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Matt Damon & His Parents
Credit: Jeff Kravitz/FilmMagic
Matt Damon celebrated his Good Will Hunting win with his parents in 1998.
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Hugh Grant & Elizabeth Hurley
Credit: Vinnie Zuffante/Getty
British "It" couple Hugh Grant and Elizabeth Hurley had all eyes on them in 1995.
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Mariah Carey
Credit: SGranitz/WireImage
For the 1999 party, Mariah Carey picked a glam wine-colored gown with silver embroidery.
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Vivica A. Fox & Dennis Rodman
Credit: Magma Agency/WireImage
The 1999 party mixed stars from all over the celebrity spectrum, including Vivica A. Fox and Dennis Rodman.
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Halle Berry
Credit: Jeff Kravitz/FilmMagic
Halle Berry stunned in champagne silk in 1998.
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George Michael and Sharon Stone
Credit: Kevin Mazur Archive/WireImage
We have "Faith" that this conversation between George Michael and Sharon Stone at the inaugural party in 1994 was a fun one.
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Quentin Tarantino & Mira Sorvino
Credit: Jim Smeal/Ron Galella Collection via Getty
Then-couple Quentin Tarantino and Mira Sorvino shared a moment before heading into the 1997 party.
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Claire Danes
Credit: Ron Galella/Ron Galella Collection via Getty
Fresh off her superstar turn in Romeo + Juliet, the actress embraced the very 1997 shade of powder blue for her Oscars outfit.
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Winona Ryder
Credit: Hulton Archive/Getty
Who wouldn't want to pose with a weenie whistle while you're in full vintage glam? Certainly not Winona Ryder.
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Prince
Credit: Ron Galella, Ltd./Ron Galella Collection via Getty
Prince looked extremely Prince-like at the inaugural party in 1994.
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Charlize Theron & Stephan Jenkins
Credit: Jim Smeal/Ron Galella Collection via Getty
Did you remember that Charlize Theron (in 1999) and Third Eye Blind singer Stephan Jenkins had dated?
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Tyra Banks & John Singleton
Credit: Ron Galella/Ron Galella Collection via Getty
Also in attendance in 1994: up-and-coming supermodel Tyra Banks and director John Singleton.
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The Judds
Credit: Jeff Kravitz/FilmMagic
Wynonna Judd, Naomi Judd and Ashley Judd had a fun family night out in 1998.
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Whitney Houston & Vivica A. Fox
Credit: Jeff Kravitz/FilmMagic
Whitney Houston and Vivica A. Fox (with Fox's then-husband Christopher Harvest) brought it in for a hug in 1999.
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Matt Dillon & Cameron Diaz
Credit: Jeff Kravitz/FilmMagic
Another oh-so-'90s couple you might not have thought about in a while: Matt Dillon and Cameron Diaz, who attended in 1998.
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Alicia Silverstone
Credit: Ron Galella/Ron Galella Collection via Getty
Alicia Silverstone looked like she could be cast in Emma at the 1996 party.
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Fran Drescher
Credit: Ron Galella/Ron Galella Collection via Getty
Fran Drescher was feeling (Nanny) Fine at the 1998 bash in this strapless tangerine number.
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Jon Bon Jovi & Dorothea Hurley
Credit: Ron Galella/Ron Galella Collection via Getty
Big hair? Cool shades? It had to be 1995.
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Julie Cypher, Melissa Etheridge, Anne Heche & Ellen DeGeneres
Credit: Jim Smeal/Ron Galella Collection via Getty
Then-couples Julie Cypher and Melissa Etheridge and Anne Heche, and Ellen DeGeneres shared a laugh at the 1998 party.
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Steven Tyler & Liv Tyler
Credit: Barry King/WireImage
Steven Tyler clearly didn't want to miss a thing daughter Liv Tyler did at the 1999 party.
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Leonardo DiCaprio
Credit: Jim Smeal/Ron Galella Collection via Getty
Leonardo DiCaprio and his date in 1995 each opted for sleek suiting.
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John Travolta & Kelly Preston
Credit: Hulton Archive/Getty
John Travolta and Kelly Preston were a happy couple at the 1996 event.
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Reese Witherspoon
Credit: Ron Galella, Ltd./Wireimage
Reese Witherspoon opted for a very 1997 brick-colored lip with her outfit.
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Alec Baldwin & Kim Basinger
Credit: Jeff Kravitz/FilmMagic
Then-married couple Alec Baldwin and Kim Basinger celebrated her win for L.A. Confidential in 1998.
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Arnold Schwarzenegger & Maria Shriver
Credit: Hulton Archive/Getty
Another couple that's since split, Arnold Schwarzenegger and Maria Shriver embodied 1998 style in periwinkle and a matching wrap for her and a baggy tux for him.
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