While we’re not yet sure what will go down at Sunday’s 92nd Academy Awards, it’s safe to predict that the Best Supporting Actress winner will not take the stage and declare herself “so in love” with her brother — and then kiss him on the lips, with gusto, at an afterparty.
That is where we were at the 2000 Academy Awards — two decades ago. The actress was Angelina Jolie, who brought her brother, James Haven, as her plus-one in a time best described as her pre-Brad Pitt but mid-Elvira period.
The Girl, Interrupted actress had also been kissy with her sibling at the Golden Globes that year — just weeks before. But she amped it up Oscar night and more people were watching (46.52 million, the show’s highest viewership in the last 20 years), so leading her speech by saying, “I’m so in love with my brother right now” didn’t go unnoticed. Nor did, “He just held me and said he loved me. Jamie … I have nothing without you.” Jolie didn’t care about any funny looks she may have gotten over it, going on to kiss him longer and lustier at the Vanity Fair Oscar afterparty, which they attended with their dad, Jon Voight, with whom they’ve had a complicated relationship.
That kiss was all anyone talked about in the wake of the show — and it hasn’t stopped being analyzed. It was called “too close for comfort” and “too family friendly” and their relationship was deemed “overtly affectionate.” Those were the nicer comments about the kiss, which was mocked on Saturday Night Live.
Jolie later criticized her critics, saying, “It wasn’t some odd open-mouthed kiss.” She was disappointed “something so beautiful and pure could be turned into a circus.” (She never gave a more detailed explanation, but a friend of her late mom, Marcheline Bertrand, later claimed the siblings arrived to the Oscars after spending all day at the hospital with their cancer-stricken mom. “Nobody in the world knew that they spent the day in the hospital. It was like, ‘Look where we’re at now,’” Cis Rundle recalled. “‘Here we are.' They only ever had each other.”)
There were hints that the 2000 Oscars, hosted by Billy Crystal, might be a weird one. Prior to the show, ballots went missing (USPS error) and then Oscars were stolen (arrests were made). But perhaps the odder things are in hindsight. How someone who was the toast of the night has disappeared from Hollywood amid a scandal. Celebrity couples from back then who now seem so strange together. Justin Timberlake’s natural hair. There were sweet things too — like mini Dakota Johnson, then 10, giving some of her first first red carpet interviews. And Crystal and the late great Robin Williams, who were close friends, sharing a hug.
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Kevin Spacey won Best Actor for playing a creepy guy.
While the American Beauty star had a big night in 2000 with no shortage of people to congratulate him for his role — as a lecherous dad with an illegal attraction to his teen daughter’s friend — he’s since disappeared, except for the occasional bizarre video message amid #MeToo allegations of him being a creepy guy off-camera as well.
Brad Pitt and Jennifer Aniston were coupled up — and had the same colorist.
While this awards season, it’s been all about whether the exes will bump into each other now that they’re both single again — and they memorably did at the Screen Actors Guild Awards — 20 years ago they were newly engaged at the Oscars. Pitt, a nominee this year, presented and then the pair — who were known to get matching "brother-and-sister" highlights back in the day — hit the Vanity Fair afterparty together. Months later, they were married and they stayed that way for almost five years — until Jolie-gate.
10-year-old Dakota Johnson was the most adorable plus-one.
The future star of Fifty Shades of Grey attended with her mom, Melanie Griffith, and then-stepdad, Antonio Banderas, and we dare you not to smile listening to how she got her dress at “sorta like a kids store.”
Timberlake was throwing off Chia Pet vibes.
‘NSync was hot — the boy band performed Best Original Song nom "Music of My Heart" with Gloria Estefan — but JT was even hotter. His romance with Britney Spears was in full swing and his fans loved everything about him, including those naturally curly locks which were wild and free (and sometimes frosted). Timberlake later lost the curls (at Tom Ford’s advice), but the internet never forgets — Ramen Noodle memes and all.
Matt Stone and Trey Parker came dressed as J.Lo and Gwyneth Paltrow.
There’s no doubt who wore it better, but the South Park: Bigger, Longer & Uncut pair, whose “Blame Canada” was up for Original Song, certainly had more chutzpah when recreating the memorable looks.
The 2000 Oscars were so long ago, Haley Joel Osment looked like this:
Osment was 11, one of the younger Oscar nominees in history for The Sixth Sense. Here’s the actor — who appeared in The Kominsky Method last year — today all grown up, bearded and without any dead people. (Well, we wouldn’t be able to see them anyway, right?)
Tom Cruise and Nicole Kidman were still married.
Talk about ages ago. Cruise, up against Osment in the Best Supporting Actor category that year for Magnolia, and Kidman were one of the biggest couples of the time. But the end was near. The pair separated around their 10th anniversary that December — bitterly. But she went on to find her soulmate, Keith Urban, who’s the only one we are used to seeing her cozying up to on a red carpet, and the split let her step out of Cruise’s shadow professionally. Just three years later, she won an Oscar for The Hours.
Scarlett Johansson was a fresh-faced teen.
Twenty years after hitting her first Oscars party at 15 without a handler to hold her giant pocketbook, the actress is a double nominee this year. She got her first two nominations in one year — Best Actress for Marriage Story and Best Supporting Actress for JoJo Rabbit.
And host Billy Crystal shared a moment with pal Robin Williams.
We’ll leave it on a sentimental note. That year, Crystal was emcee of the show — his seventh time hosting — and after he caught up with his decades-long pal Williams, who performed “Blame Canada” during the show. Considering how infamously great their voicemails to each other were, can you imagine a real-life conversation? We’re sure it was gold.
The 2020 Academy Awards will air live from the Dolby Theatre in Hollywood, Calif., on Sunday at 8 p.m. ET/5 p.m. PT. Catch it on ABC, ABC.com or watch it through a streaming provider that offers the network, including Hulu With Live TV, YouTube TV, or DirectTV Now, all of which offer a free trial period.
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