The rest of the red carpet, however ...

By Isabel Jones
Updated Feb 22, 2019 @ 11:00 am

Twenty years ago, the landscape of Hollywood was completely different than it is today. There’s perhaps no better testament to this than a look back at the industry’s biggest night: The Oscars. Scroll down below for an overview of the 1999 ceremony.

The Host

One possible parallel? Rumors abound that Whoopi Goldberg will step in to host the otherwise host-less 2019 Oscars. (Her co-hosts on The View refute the rumor, noting that Goldberg has been suffering from pneumonia and not prepping for the show. But we can dream.) The comedian hosted in 1999, giving the gig her all (and even dressing up as some of the nominees). Here she is as Queen Whoopi I, an interpretation of nominee Cate Blanchett’s portrayal of Queen Elizabeth I in Elizabeth.

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P.S. Here’s the actual Ms. Blanchett, looking understated yet fabulous in a thin knit Galliano gown with a floral motif lining the top hem and decorating the open back.

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The Winners

The night’s big winner was Shakespeare in Love and its leading lady, Gwyneth Paltrow. Clad in a prom-appropriate pink Calvin Klein gown and diamond choker, the young ingenue accepted the award for Best Actress in a Leading Role.

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Of course, the film’s other major Oscars coup, Best Picture, gave the now disgraced producer Harvey Weinstein his first (and only) Oscar.

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The Carpet

Like this year’s ceremony, the 1999 red carpet was graced by Jennifer Lopez, who was looking like American royalty in a strapless black ball gown with an embellished top, her hair back in an elegant bun.

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Other notable fashion moments came from Celine Dion in her iconic backwards suit, Catherine Zeta Jones’s glittering red strapless gown, and Uma Thurman’s Grecian two-piece.

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The Couples

Though there are a couple mainstays (hi, Goldie and Kurt!), most of the 1999 Oscars duos are long, long over.

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Drew Barrymore punctuated a brief relationship with nominee Ed Norton on the carpet in a body-hugging velvet gown.

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Ellen DeGeneres coordinated with then-girlfriend Anne Heche in white outfits and matching sunglasses.

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Laura Dern and Billy Bob Thornton made one of their last red carpet appearances as a couple. Less than a year later he shocked the world (and Dern) when he wed Angelina Jolie in Las Vegas.

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While not a legitimate “couple,” Boston-native besties Matt Damon and Ben Affleck couldn’t keep their hands off each other on the carpet.

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The "OK, Sure"

Though both Drew and Liv Tyler attended the Oscars with dates (Liv’s was her rocker dad Steven Tyler, but still), the leading ladies indulged in a lip-lock on the carpet. Why? We really couldn’t tell you.

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The Controversy

Esteemed director Elia Kazan (actress Zoe Kazan’s grandfather) was honored with a lifetime achievement award at the 1999 ceremony, but many watching were reluctant to applaud his career. According to the L.A. Times, about 500 protestors gathered outside the venue that afternoon to refute the Academy’s decision.

The cause for uproar? More than 45 years prior, Kazan was asked to share his testimony with the House of Un-American Activities Committee and informed on eight of his friends from the Group Theater who, like himself, had previously claimed allegiance to the Communist Party. His actions effectually blacklisted his friends in the industry, and decades later he had yet to apologize.