On Feb. 10, 2019, the 61st Annual Grammy Awards will air live from Los Angeles. As usual, today's hottest music and entertainment stars will be wearing weird, wild and truly wonderful fashion for us to enjoy. In honor of the prestigious award show, Wonderwall.com is flashing back 20 years to see what the celebrities of yesteryear wore on the Grammys red carpet in 1999… starting with the Material Girl. Although Madonna has never been afraid to strike a fashion pose, her look at the 1999 Grammys, where she won three awards including best pop album, seemed more head-scratching than head-turning. Madge's plain white tank with bedazzled lavender Gucci pants and a bold red lip was one of our least favorite looks of the night. Keep reading to see what other celebs wore to the last Grammys of the 20th century…
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Although this pic was taken one year before Jennifer Lopez made fashion history at the Grammys with her deep-V green Versace gown, we still have to give her look at the 1999 award show props. Jenny from the block was sitting pretty in this gold mini with a delicate gold lace hem. Jennifer's '90s-style chunky highlights, however, left us less than dazzled.
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Will Smith was also at the 1999 Grammys, where he took home the award for best rap solo performance for his song "Gettin' Jiggy Wit It." While Will might have been at the height of his musical career, his fashion game was on a losing streak. This boxy-fit, two-tone leather suit and gold chain look was borderline cringe-worthy and only made tolerable by Will's gorgeous smile and well-deserved win.
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Will Smith's wife, Jada Pinkett Smith, arrived at the 1999 Grammys looking like a statue herself in this gold satin cut-out gown with a matching head wrap and knee-high gladiator heels. The dress showed off Jada's enviable post-pregnancy abs and unbelievably toned arms, although it didn't land her on any best dressed lists for the night.
Seeing him holding his very first Grammy — for best Latin pop performance for his song "Vuelve" — it's hard not to get the feels for Puerto Rican singer Ricky Martin. The handsome, smiling music star donned a very '90s look with this muscle-mugging ribbed sweater and baggy black leather pants.
Husband-and-wife country music stars Faith Hill and Tim McGraw pulled off contrasting looks at the 1999 Grammys. Faith, who was nominated for three awards that night including best country album, wore a pale lavender sheath with a matching shawl. Tim, who also earned a Grammy nod that night, kept his look cowboy cool with a black suit and hat that he brightened up with a white dress shirt and tie.
Celine Dion kept her style simple but sexy at the 1999 Grammys. The French-Canadian singer donned a sleek gray evening gown that featured a single glittering shoulder strap while holding her two Grammys for record of the year and best female vocal pop performance that night.
John Tesh and his wife, actress Connie Sellecca, arrived at the 1999 Grammys in their evening best to celebrate John's nomination for best new age album. While John opted for an elongated jacket with a silver double-breasted vest, Connie donned a plush purple velvet coat with toggle buttons over a matching satin evening gown.
Not only did Lauryn Hill break a record in 1999 as the female artist with the most Grammy wins in one night (she took home five awards), but she did it in style. The "Doo Wop (That Thing)" artist rocked a decidedly cool and colorful look in this Giorgio Armani skirt that featured flowing layers of green, blue, orange and red satin paired with a simple midriff-baring black top.
While Aerosmith band members Tom Hamilton and Joe Perry (far left and right) kept their 1999 Grammy looks traditional rock 'n' roll in all-black, fellow rockers Brad Whitford, Steven Tyler and Joey Kramer weren't afraid to play with color. We especially love Steven's lengthy white tuxedo jacket and pants, which he paired with a black vest (and no undershirt). The band won a Grammy that night for best vocal performance by a group.
Winning Grammys for best country performance and best country album, The Dixie Chicks members Emily Robison, Natalie Maines and Martie Maguire pulled off a complementary look that allowed their individual styles to shine through. While all the ladies opted for mostly black, midriff-baring attire with metallic embroidery, Emily (left) donned loose-fitting slacks while Natalie (center) chose a sparkly miniskirt and Martie (right) wore a floor-length skirt with a thigh-high slit.
Single-name songbirds Brandy and Monica looked angelic at the 1999 Grammys. The winners of the award for best R&B performance by a duo for their hit song "The Boy is Mine" shined in their color-coordinated outfits. Brandy paired white slacks and a champagne-colored crop top with a floor-length white suit jacket while Monica donned a floor-length sleeveless white gown with a coordinating satin armband.
We love Sheryl Crow, but we definitely don't love her all-black look at the 1999 Grammys. Sheryl, who won the prize for best rock album that year, paired a tea-length pencil skirt with a black corset top, which, on their own, wouldn't have looked half bad. Her fashion faux pas was that hideous long-sleeved micro-shrug that was awkwardly buttoned at the bottom. Not to kick a dead horse, but that giant black watch wasn't helping her look either.
Clint Black, who won a Grammy for best country collaboration in 1999, upgraded his style — trademark cowboy hat, black T-shirt and light-wash denim — with a snazzy black suit jacket at the award show that year. Wife Lisa Hartman Black, however, chose a bizarre and unflattering cerulean blue digital-patterned suit that she paired with overly messy hair, pulling our attention away from her husband's win and toward her questionable fashion choices.
Country music star Shania Twain had us doing a double take at the 1999 Grammys. The Canadian singer, who won awards for best female country performance and best country song, arrived at the Grammys in this floor-length long-sleeved turtleneck gown dotted with iridescent sequins. That same night, Shania stepped on stage to perform her hit song "Man, I Feel Like a Woman" vamped up in a black miniskirt, corset top, opera-length gloves and a thick black choker, proving she could pull off daring and demure styles in the same night.
Erykah Badu channeled her African roots in this colorful handmade gown and head wrap at the 1999 Grammys. While we love the look, we're not so hyped about Erykah's beaded satchel bag or mismatched gladiator-style cork-platform sandals. Swap them out for a neutral clutch and strappy heels and Erykah's Grammy style would have been mesmerizing.
We could barely remember that Brian Setzer won his first two Grammys at the 1999 award show because his oversized and extremely gaudy gold suit outshined his achievement. The "Jump, Jive An' Wail" musician's awards almost blended in with his jacket, making it hard to tell where they ended and his bad fashion choices began.
Monochrome never looked more magnificent. Singer and songwriter Emmylou Harris, who won the award for best country collaboration, took our breath away at the 1999 Grammys in this burnt orange satin gown and matching shawl. Not only was the color choice an amazing contrast with Emmylou's salt-and-pepper hair, but the playfully ruffled hemline gave the dress and shawl a sense of movement that made her look as if she was dancing amidst a soft breeze.
We're not trying to pick on country music star Rick Trevino's 1999 Grammys look, but everything about his denim makes us cringe. While the top half of his outfit was attractive (we actually love the pop of color from his striped vest), those basic blue jeans, which seemed to pull around his groin, threw the look way off and managed to make him look shorter than he actually is. While jeans and suit jackets can be a winning combo, this was a fashion miss.
"Party of Five" star Jennifer Love Hewitt's dress at the 1999 Grammys looked like she wrapped a curtain around her body and added heels. The tea-length sleeveless shift did nothing to accentuate Jennifer's figure. We really don't like the mid-calf hemline either. Had the dress stopped just around Jennifer's knee, it actually wouldn't have looked half bad.
Smashing Pumpkins frontman Billy Corgan channeled "The Addams Family" at the 1999 Grammys. Posing with then-girlfriend Yelena Yemchuk, a photographer, Billy looked as if he were auditioning for the part of Uncle Fester in his double-breasted pinstriped jacket and matching kilt with knee-high boots. Yelena, on the other hand, was far more stylish, donning a full-length black skirt with a simple white long-sleeved tie-front blouse.
The one positive of Australian singer Natalie Imbruglia's mirror-adorned trench coat is that she could easily check her hair and makeup throughout the night. The "Torn" singer's 1999 Grammys look felt more silly than serious, especially given that Natalie was up for three awards including best pop album.
The Backstreet Boys members Howie Dorough, Nick Carter, AJ McLean, Kevin Richardson and Brian Littrell showed up to their first Grammy Awards in adorably matching attire. While it's typical for music groups to wear a similar style on the red carpet (see these Destiny's Child throwback pics), the Backstreet Boys took their fashion unity in a fun direction by giving AJ central focus in his pimp-inspired all-white tuxedo.
It's so hard to love a singer such as Sarah McLachlan while simultaneously hating her Grammys fashion. The Canadian songbird, who was nominated that night for best female pop vocal performance, wore a tragically ill-fitting blue gown with awkwardly placed satin paneling and pleats accompanied by a plum shawl. The baggy dress bunched in all the wrong places, giving Sarah a lumpy frame. Plus the deeper hues contrasted with Sarah's auburn hair, giving her a bit of a washed-out look.
Sometimes rocking a single print head to toe is a recipe for a fashion disaster, but for singer Mya, it totally worked. Donning a shimmery blue floor-length floral-print kimono with a matching tube top and capris, the "Ghetto Superstar" singer allowed her décolleté and midriff to break up the monotony of the outfit, giving it a fresh look.