America's sweetheart took home Best Actress in a Leading Role for her instantly iconic performance in Erin Brokovich.
At the time, J.Lo and her former backup dancer were just months away from tying the knot. They'd go their separate ways after less than a year of marriage.
Only a year later, the A-lister would make history by becoming the first Black woman to win an Oscar in the Best Actress in a Leading Role category.
The Hollywood heartthrob brought his signature smolder to the 2001 Academy Awards.
It's not hard to see why the Icelandic artist's swan dress instantly became one of the most memorable red carpet moments of all time.
Power couple alert: Tom earned a nomination for Best Actor thanks to his unforgettable performance in Castaway.
The Crouching Tiger, Hidden Dragon star wowed in a stunning, black and gold beaded gown.
Kate, who brought her then-husband and The Black Crowes rocker to the ceremony, earned a Best Supporting Actress nomination for her performance in Almost Famous.
The two-time Academy Award winner brought sunshine to the red carpet in this bright yellow ensemble.
The 2001 Best Supporting Actor nominee and his late sibling, River Phoenix, made Oscars history as the first pair of brothers to receive acting nominations.
Dressed in an eye-catching white pantsuit, the actress brought her famous father as her plus-one.
Baby on board! The longtime couple was pregnant with their first child, a son they named Keen Ruffalo.
Who's that girl? It's the New Girl star without the brunette bangs she's been known for over the years.
The Pulp Fiction star and his wife of more than four decades enjoyed a night out on the town.
Ten things we hate about this fashion flashback? Absolutely nothing.
The Million Dollar Baby star looked like a million bucks as she attended the Oscars alongside her former husband of less than a decade.
It's the winners' circle! Benicio took home the Best Supporting Actor honor for his performance in Traffic, while Marcia was awarded Best Supporting Actress for Pollock.
The Vicky Cristina Barcelona actress proved elegance never goes out of style in this stunning off-the-shoulder gown.
The two-time Oscar nominee attended the 2001 ceremony as a presenter.
Russell won his first Oscar for Gladiator in 2001.
Twenty years after receiving a nomination for Best Supporting Actress, Frances is up for her third Oscar win at the 2021 ceremony for Nomadland.