2000 Academy Awards fashion flashback

By Megan Riedlinger 8:12am PST, Jan 9, 2020

The Academy Awards will be handed out on Feb. 9, 2020! But before Hollywood's biggest night takes place, Wonderwall.com is taking a trip down memory lane. Let's check out what the Oscar red carpet looked like 20 years ago back in 2000… First up? Gwyneth Paltrow, who seriously underwhelmed in a boring gray slip dress and super-casual tassel necklace. She presented the best actor award at the ceremony that year. Keep reading to see the rest of the stars' Y2K Oscars fashion…

Hilary Swank arrived at the 2000 Academy Awards in this bold olive green ballgown. She accessorized the strapless confection with plenty of bling in the form of an eye-catching necklace. Hilary took home a best actress that night for her performance in "Boys Don't Cry."

It was all about black for Angelina Jolie during this era. Angie sported a long-sleeved, floor-length black gown that matched her equally dark hair in 2000. She won the Oscar for best supporting actress that night for her work in "Girl, Interrupted" and afterward made headlines when she kissed brother James Haven — her date that night — on the lips at the Vanity Fair Oscar Party.

Nicole Kidman arrived at the 2000 Academy Awards looking like an Oscar statue herself in a bold gold Dior dress. Her date that night? Then-hubby Tom Cruise, who looked dapper in a tux. He was up for best supporting actor for his performance in "Magnolia" but lost to Michael Caine in "The Cider House Rules."

"South Park" creators Matt Stone and Trey Parker made a splash on the red carpet at the 2000 Academy Awards when they arrived dressed like other stars. Matt wore his own version of Jennifer Lopez's iconic Versace Grammys gown, while Trey — who was nominated for best original song that night for "Blame Canada" from the movie "South Park: Bigger, Longer & Uncut" — donned a pretty pink gown that paid homage to Gwyneth Paltrow's Oscars frock from the previous year.

Charlize Theron's burnt orange Vera Wang dress was so amazing, it's been put on numerous "best Oscar gowns of all time" lists. The halter-style frock featured a plunging neckline and embellishments at the base of the straps, but it was that unique color that made the gown so memorable.

Sure, Antonio Banderas and Melanie Griffith looked great on the 2000 Academy Awards red carpet — but do you recognize that little girl between them? That's a young Dakota Johnson, Melanie's daughter with ex-husband Don Johnson, who tagged along in this shiny gown and white sandals at just 10 years old.

In 2000, Heather Graham was a stylish star to watch and here's a perfect reason why. She arrived at the Academy Awards in this intricately beaded gown with thin straps and added a dramatic collared necklace and fancy clutch to complete her ultra-glamorous look. She presented the award for best sound with Mike Myers that night.

Haley Joel Osment arrived looking sharp in this little suit and bow tie. He was up for best supporting actor for his work in "The Sixth Sense" that year.

Did you know that singer Sarah McLachlan was at the 2000 Academy Awards? Now you do! The Canadian music star wore this pink-and-white strapless dress and accessorized with a pale pink shrug. She performed the song "When She Loved Me" from "Toy Story 2" with Randy Newman during the broadcast.

Penelope Cruz made a bold statement in blue on the 2000 Oscars red carpet. She also wrapped herself in a sheer shawl and accessorized with a dainty diamond necklace. During the ceremony, she presented best foreign language film with Antonio Banderas.

Tyra Banks gave us serious princess vibes at the 2000 Academy Awards. The supermodel showed up in this strapless purple confection, which featured a full tulle skirt and stood out amongst the slinkier dresses that night.

This is a pretty understated look from Chloe Sevigny! The "Boys Don't Cry" star, who typically pushes the fashion envelope, opted to play it safe in 2000, arriving in this beautiful black halter-style dress with a plunging neckline and a belt detail. She lost out to Angelina Jolie in the best supporting actress category that night.

Angela Bassett rocked a strapless red column dress with embellishments along the bodice that looked exactly like the jewels around her neck and on her ears! We loved this bold style move from the star in 2000.

Vanessa Williams went for a look that was simple and in basic black in 2000. The star arrived at the Oscars in this sleek halter-style gown that glamorously showed off her baby bump (daughter Sasha Fox arrived a few months later in May). When it came time to add some sparkle, Vanessa opted for a pretty diamond necklace.

Queen Latifah kept things regal in a shimmering gray gown with long sleeves, a floor-length skirt and a delicate diamond necklace. That night, the star performed a medley of music alongside other artists including Garth Brooks, Faith Hill and Dionne Warwick.

Gloria Estefan was a vision in red in this off-the-shoulder design on Oscar night in 2000. From the long sleeves to the fitted bodice to the mermaid-style skirt, the gown was lovely — but her choice to accessorize with pink and red gemstones wasn't the smartest decision. The singer performed that night, singing "Music of My Heart" with *NSYNC.

*NSYNC arrived at the Academy Awards in 2000 looking quite dapper — though they didn't do their usual matching thing. Some of the boy band members — Justin Timberlake, JC Chasez and Joey Fatone — wore white dress shirts, while Lance Bass stood out in black and Chris Kirkpatrick wore red. The pop stars were on hand to perform "Music of My Heart" from the film "Music of the Heart" with Gloria Estefan.

Julianne Moore opted for this unique number in black. Though we loved the off-the-shoulder detail and the pleated skirt, she lost us with that odd structured semi-sheer bodice. The star was up for best actress for her work in "The End of the Affair" that night but lost to Hilary Swank in "Boys Don't Cry."

Mena Suvari looked statuesque in this sleeveless silver design with mosaic-like embellished detailing. The "American Beauty" actress presented the award for best documentary short subject during the ceremony that night.

Ashley Judd made her mark in purple, arriving in this slimming gown with spaghetti straps and a matching shawl.

Another star who picked purple? Salma Hayek, who hit the oscars red carpet in this lilac halter-style gown and accessorized with a matching tulle wrap that blended in with the frock seamlessly. The movie star was a presenter that night.

Lucy Liu rocked a lovely one-shouldered number with a graphic pattern in various hues of red. She added strappy red heels, but our favorite accessory was the chunky diamond bracelet she donned.

Erykah Badu brought bright shades of green and yellow to the Oscars red carpet. The singer-actress chose a bold halter-style design with green leather and yellow rafia stitching and completed her look with a matching head wrap. She presented the award for best makeup alongside Tobey Maguire later that night.

It was semi-sheer and silver for Garcelle Beauvais at the 2000 Academy Awards, where the actress hit the red carpet in an edgy off-the-shoulder gown. Adding some extra sparkle? Her very of-the-era choker necklace.