Oscars Flashback: Madonna, Dolly Parton, and More Stars of the 2006 Vanity Fair Oscar Party

Oscars Flashback: Madonna, Dolly Parton, and More Stars of the 2006 Vanity Fair Oscar Party

The Vanity Fair Oscar Party is entering a new era. As the 2026 edition festivities move to LACMA—the Los Angeles County Museum of Art—we’re taking a moment to revisit the 2006 Vanity Fair Oscar Party.

Twenty years ago, Oscar honorees like Dolly Parton (nominated for her original song in Transamerica), Keira Knightley (best actress nominee for Pride & Prejudice), and Jake Gyllenhaal (best supporting actor nominee for Brokeback Mountain) descended upon Morton’s in West Hollywood, where they toasted the year in film. The Academy spread the wealth at the 2006 Oscars—bestowing three awards apiece on four of the nominated films, including Rob Marshall’s Memoirs of a Geisha, Peter Jackson’s King Kong, and Paul Haggis’s Crash, which pulled an upset to win best picture over Ang Lee’s Brokeback Mountain, which claimed directing, screenplay, and original score trophies.

Let’s travel back to the Jon Stewart-hosted 78th Academy Awards, held on Sunday, March 5, 2006. During the broadcast, George Clooney became a first-time Oscar winner for best supporting actor in Syriana—one of many that evening to win a statue on their first nomination. (“Good Night, and Good Luck. It’s not just Mr. Murrow’s sign-off,” Stewart cracked in his monologue of Clooney’s other nominated movie that night: “It’s how Mr. Clooney ends all of his dates.”) That was also true of hip-hop group Three 6 Mafia, whose Hustle & Flow track “It’s Hard Out Here For a Pimp,” won best original song. After their victory, Stewart quipped onstage, “Martin Scorsese: Zero, Three 6 Mafia: 1.” (The following year, Scorsese finally won best director for The Departed, his seventh Oscar nomination.)

Inside the 2006 Vanity Fair Oscar Party, one could spot bygone celebrity couples like Jennifer Lopez and Marc Anthony and Heidi Klum and Seal. After winning her best actress Oscar for playing June Carter to Joaquin Phoenix’s Johnny Cash in Walk the Line, Reese Witherspoon (wearing a vintage champagne-hued Dior gown) and then husband Ryan Phillippe floated into the soiree. They were joined by fellow newly minted winners including Philip Seymour Hoffman, clutching his best-actor Oscar gold for playing Truman Capote in Capote and Rachel Weisz, who took home best supporting actress for The Constant Gardener while pregnant with her son with director Darren Aronofsky.

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