By Wonderwall.com Editors
5:49am PDT, Oct 13, 2020
On Oct. 14, the 2020 Billboard Music Awards return to honor the top musicians of the previous year. The show, which was originally scheduled for April and postponed amid the coronavirus pandemic, will be hosted by Kelly Clarkson for the third year in a row. As we gear up for the big night, Wonderwall.com is flashing back to 2000 to check out what music's biggest names wore on the red carpet 20 years ago, starting with Britney Spears. Britney, who won two awards for her album "Oops!… I Did It Again," walked the red carpet in a bikini top and booty shorts with pink fishnet stockings underneath. She topped her outfit with a long pink-and-orange duster and accessorized with maroon suede boots, a wild orange-and-purple fedora and an elaborately beaded choker — interesting choices. Keep reading for more nostalgia-inducing style moments from 2000…
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Best pop new artist winner Pink must have felt rich as she posed backstage at the Billboard Music Awards in a sheer gown in a bold cash print. Even her evening bag had currency printed on it! The singer also went for an unusual hair choice — a spiked, rainbow-colored 'do.
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The ladies of Destiny's Child — Kelly Rowland, Beyonce and Michelle Williams — walked the red carpet at the Las Vegas event looking like absolute queens. Kelly choose a high-low red strapless flowered gown, Beyonce picked a form-fitting beaded yellow dress and Michelle wore a black frock with a high neck and a high leg slit. They all looked flawless!
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At the 2000 Billboard Music Awards, the ladies of Destiny's Child took home four trophies including artist of the year. Inside the show, Michelle Williams, Beyonce and Kelly Rowland changed into matching dresses, each in the same print but in a cut that suited their own style.
Jessica Simpson attended the 2000 Billboard Music Awards as a nominee for top new artist. For her big night, the then-20-year-old singer wore a short, strapless black dress with tall matching black boots. She jazzed up the look by adding shiny pink fringe sleeves.
Faith Hill won two awards in 2000 for her song "Breathe." She accepted in a simple black flowy one-shoulder cocktail-length dress. She wore her hair in loose curls and paired the long-sleeved frock with strappy sandals.
For her performance at the Billboard Music Awards, Faith Hill got a little more casual. The country music singer changed out of her dress and into a black sleeveless top and embellished jeans that were ripped and put back together with safety pins along her thighs.
Comedian Kathy Griffin, who co-hosted the show with the guys from *NSYNC, walked the red carpet in Las Vegas in 2000 swallowed by plaid. She wore plaid pants, a long plaid jacket over a green vest and a matching plaid hat — creating a bit of an eyesore.
Mandy Moore looked as sweet as can be at the 2000 Billboard Music Awards, which were held on Dec. 5, 2000. The pop star wore a simple pink dress with a loose satin ribbon tied at the waist. She kept her accessories simple and wore peep-toe heels the same color as her dress.
Actress Mila Kunis attended the event in a pair of boot-cut jeans with square-toed boots. She wore a belt with a large buckle and a rock 'n' roll tee on top. She covered up her super-casual look with a patchwork calf-length jacket. For her makeup, Mila went with very dark eyes, which, coupled with the streaks of pink and purple in her hair, had a goth effect.
The guys of *NSYNC — Lance Bass, JC Chasez, Chris Kirkpatrick, Joey Fatone and Justin Timberlake — co-hosted the Billboard Music Awards back in 2000. The boybanders all went out-there with their fashion choices. Among the more outlandish decisions were Lance's lamé pants with a tiger-print T-shirt and a white jacket as well as Joey and Justin's shiny T-shirts under their jackets.
Top female artist winner Christina Aguilera rocked a black-and-white look in 2000 that matched her blonde hair with black-dyed tips. The singer wore a simple, white cocktail dress with a draped neckline along with heavy black sparkly boots that went up to her knees, weighing down the look.
No Doubt's Gwen Stefani attended the Billboard Music Awards with bandmates Tom Dumont, Adrian Young and Tony Kanal, who all pulled out their best punk styles. Gwen choose a more casual look for the event — dark low-rise wide-legged trousers with a white tank and a red leather vest on top. She finished off the look with her signature red lip.
The guys of 98 Degrees — Drew Lachey, Jeff Timmons, Justin Jeffre and Nick Lachey — came to the 2000 show together looking a bit more conservatively dressed than their counterparts in boy band *NSYNC. Drew did go with a more sheer button-down and Nick's shirt had a little sheen to it, but Jeff kept things traditional with a white dress shirt while Justin simply threw a purple shirt over a black tee. All in all, pretty safe choices.
Naturi Naughton, Kiely Williams and Adrienne Bailon of 3LW all got funky for their walk down the awards show red carpet. Naturi wore a denim jacket over maroon crocodile-print leather pants, Kiely kept up the animal print with pink snakeskin trousers and Adrienne wore a two-piece leather jacket and skirt set in a super-girly shiny pink color.
Aaron Carter was just a teenager at the 2000 Billboard Awards! The pop star dressed age-appropriately in a white T-shirt with a long, casual blazer on top and red leather-look trousers.
Bow Wow was still known as Lil' Bow Wow when he walked the 2000 Billboard Music Awards red carpet at 13. The rapper was clearly trying to look older in his fur coat, long diamond necklace and leather pants.
Backstreet Boys singer Howie Dorough was working a long, very flat-ironed hairstyle in December 2000. The boybander attended the Billboard Music Awards sporting that shiny hair along with a sparkly blazer, giving him an all-around sheen.
Toni Braxton seemingly stepped right out of the '70s with her Billboard Music Awards look. Toni, who took home the prize for R&B artist of the year, wore a pale yellow halter-style jumpsuit with a matching belt and headband.
Matchbox Twenty frontman Rob Thomas walked the Billboard Music Awards red carpet in a button-heavy blazer with wife Marisol on his arm. She choose a casual, popular look that was in style at the time — a peasant skirt and and a black cropped T-shirt accessorized with an oversized cross necklace.
Samantha Mumba decided to forgo the rules of matching and paired a baby pink draped blouse with a baby blue embellished miniskirt and a silver belt. Th singer topped the outfit off with a cropped brown fur coat and knee-high brown leather boots.
Sisqo cleaned up at the 2000 Billboard Music Awards, taking home best new artist and best male artist trophies, among others. The "Thong Song" entertainer attended wearing a gray printed sweatsuit with a matching do-rag and a long chain necklace.
Singer Carnie Wilson wore an eggplant-colored belted blouse with brown pants, which made her look more ready for work in a cubicle than a glamorous night out in Las Vegas. The only fun part of her outfit was her turquoise eyeshadow!
Singer Brian McKnight donned a butterscotch-colored leather jacket over a white T-shirt and accessorized with a turquoise belt when he walked the red carpet at the MGM Grand Garden Arena in 2000.
Comedian Carrot Top paid homage to Mick Jagger with his Billboard Music Awards look. The fiery redhead paired a T-shirt with the icon's face on it with a pair of sport pants — by far the most casual look of the evening.
Persia White of "Girlfriends" fame arrived at the December 2000 event with singer Jill Marie Jones. Persia choose a black-on-black look with black pants, boots and a black leather jacket. Jill also wore a black top with black pants and boots but added a longer animal-print jacket to break up the monotony.
Tony Hawk showed up to the Las Vegas award show in an outfit that could have worked 20 years prior and even today. The skateboarder brought long then-wife Erin Lee, who choose a casual look — a giraffe-printed skirt and a black tube top.
Dance music artist Kristine W posed for photos in a unique ensemble. The singer wore a black short bottom with pantyhose underneath and a Louis Vuitton crop top. She added a long suede vest over the whole outfit as well as a fur stole.
