Goth Angelina Jolie Flipped the Oscars on Its Head 20 Years Ago

Success is nothing new to Angelina Jolie. She’s been riding the wave of critical acclaim for decades, the earliest concrete example manifesting in the year 2000, when she won an Oscar at 24 years old.

And though awards and wins are now pretty commonplace for Jolie, there are a few things that have changed (a lot) for the acress and mother-of-six.

While Jolie is still a proponent of the all-black wardrobe, she’s certainly lightened things up in the 20 years since her Oscars win. The actress arrived at the 2000 ceremony in a long-sleeved column gown from designer Marc Bouwer. She furthered the gothic vibe with straight black hair flowing past her waist and a bold cat-eye.

Another major lifestyle change for Jolie? Uh, red carpet PDA ... with her brother.

Jolie’s big brother James Haven was, for a time, the actress’s go-to awards show date. Neither party was shy about their love for each other, which would occasionally result in an incredibly public kiss, as it did at the Oscars.

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