To celebrate the 2019 Billboard Music Awards on May 1, Wonderwall.com is taking a look back at some of the best red carpet fashion moments from the 1999 Billboard Music Awards, starting with Mariah Carey's look. The music diva left little to the imagination in this forest green, halter-style crochet dress paired with green strappy heels. Keep reading for more memorable fashion looks from the show 20 years ago…
Britney Spears looked '90s-chic at the 1999 Billboard Music Awards where she wore a lavender floor-length gown. She completed the look with a white shawl and dainty silver jewelry.
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JAY-Z sported a denim-heavy look at the 1999 Billboard Music Awards — an oversized jean jacket with a white T-shirt, baggy blue jeans, diamond studs and black boots.
Actress Anne Hathaway dazzled at the 1999 Billboard Music Awards in a black off-the-shoulder top, a gray satin skirt with black beading and trim, a black choker necklace and black strappy heels.
Mandy Moore was every bit the bubblegum teen star at the 1999 Billboard Music Awards. The future "This Is Us" actress rocked a pink-sequined sleeveless turtleneck with a pink-and-green plaid maxi skirt. Adorbs!
Jennifer Lopez performed in a sheer metallic mini and bikini-style top during the 1999 Billboard Music Awards at the MGM Grand Garden Arena in Las Vegas.
Mary J. Blige rocked this fierce look to the 1999 Billboard Music Awards — black leather pants and a matching jacket with a brown fur coat, black boots and white sunglasses.
Christina Aguilera showed off her enviable abs at the 1999 Billboard Music Awards in a purple-and-pink crop top with white fringe and a pink maxiskirt with a sheer overlay.
Jennifer Love Hewitt continued the tiny-top trend at the 1999 Billboard Music Awards in a black tube top and a black-and-silver sequined maxiskirt with a high slit. The actress finished her look with black strappy heels.
A teenaged Mila Kunis rocked black satin pants and a gray sequined tank top at the 1999 Billboard Music Awards. '90s swag!
Snoop Dogg made sure to shout himself out with his outfit at the 1999 Billboard Music Awards. The rapper rocked a gray Dickie's suit with a diamond chain and a blue leather jacket with signage from his music label, Dogg House Records, across the front.
At the 1999 Billboard Music Awards, Jessica Simpson proved that you can never go wrong with a little black dress — in this case, a sequined black midi-length frock with a square neckline.
Aerosmith bandmates Steven Tyler and Joe Perry went for rock-star chic at the 1999 Billboard Music Awards. Frontman Steve donned red paisley-print pants with a black velvet shirt with red trim, black boots and a printed tan, red and yellow duster jacket. Joe opted for a more understated look: black leather pants and a black leather jacket with a sequined black button-down shirt, black sunglasses and black boots.
Ricky Martin was livin' la vida loca back at the 1999 Billboard Music Awards where he donned a gray button-down shirt and black pants.
Vitamin C made quite a statement at the 1999 Billboard Music Awards thanks in part to her striking yellow-green hair. The singer accentuated her locks with a green satin jacket, blue pants and platform sandals.
R&B music group Blaque rocked furistic fashion at the 1999 Billboard Music Awards. Natina Reed went for a purple leather two-piece ensemble with matching boots, while bandmate Brandi Williams wore a black leather crop top and pants with platform boots. Shamari Fears completed the trio's look with a pink leather crop top and skirt with gray platform boots.
Country music singer LeAnn Rimes combined some of the night's biggest fashion trends for one '90s-centric outfit at the 1999 Billboard Music Awards — glittery black PVC pants with an ombre pink fringed crop top and black pumps.
Brian McKnight channeled his inner "Blade" at the 1999 Billboard Music Awards in a long black leather jacket, black leather pants and black patent-leather shoes.
Former teen heartthrob Andrew Keegan went for a black leather jacket, black pants and a silky gray button-down shirt at the 1999 Billboard Music Awards. Swoon!
Kathy Griffin made an entrance in this metallic floor-length leather gown at the 1999 Billboard Music Awards.
Pop-punk band blink-182 rocked their classic '90s look at the 1999 Billboard Music Awards. Drummer Travis Barker wore a black T-shirt with brown cargo pants, tall socks and sneakers, while singer-guitarist Tom DeLonge opted for a black jacket, gray shirt, white undershirt and green cargo pants with Chuck Taylor sneakers. Singer-bassist Mark Hoppus completed their casual chic look with a red sweater, blue pants and blue sneakers.
"Mambo No. 5" singer Lou Bega looked suave in a white fedora hat, black suit jacket, white shirt and gray pants at the 1999 Billboard Music Awards.