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The Most Stylish VMA-Nominated Videos

Twenty-five classic looks, from Michael Jackson’s zombie attire to Britney Spears’ school girl outfit

The Most Stylish, VMA-Nominated, Videos, music videos

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Twenty-five classic looks, from Michael Jackson's zombie attire to Britney Spears' school girl outfit

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Garbage, ‘Push It’ (1998)

Unnerving, modern and stunningly original,"Push It" represents the best tenets of the ambitious lates 90s video domain. Garbage paired up with Italian neo-surrealist cinematographer Andrea Giacobbe for the clip, reportedly spending half a million dollars and triggering a car accident in the four-day filming process. The cost in money and blood was worth it: "Push It" is still regarded as Garbage's crown video jewel, as well as the most confusing/inventive/perverse video of 1998. It could also be considered a living, moving fashion editorial for a progressive Euro rag, with Shirley Manson (and her lightbulb-head "husband") providing more attractive psychic intensity than any model could. Despite its whopping eight VMA nominations, "Push It" won nothing, but never fails to rattle, confound, and delight viewers to this day.

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Aaliyah, ‘Are You That Somebody?’ (1998)

In 1998, Aaliyah was America's urban sweetheart, and this Timbaland-maestroed paean was her epitomizing moment in style and sound. Dressed casually in the type of relaxed but sexy athletic gear that cool women adored in the late 90s, she made baggy pants and crop tops look great, and radiated with confident ease. Her metallic makeup betrays its era, but as our collective eye readjusts to a 90s-friendly setting, that intense, mauve eye and lip will soon look au courant again. Nominated for two VMAs in 1999, the video's impact of multiple genres would be felt for years to come. Though Aaliyah would go on to make many visually striking videos before her devastating death in 2001, "Are You That Somebody?" holds the elements that define it as her greatest — the one that captivates us the most, even still.

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Lauryn Hill, ‘Doo Wop (That Thing)’ (1998)

When Lauryn Hill released "Doo Wop (That Thing)" in 1998, she eschewed the Y2K-obsessed posturing of hip-hop entirely, and made a killer female empowerment anthem that paid tribute to the soulful sounds of the 1960s. Somehow that retro maneuver felt progressive, especially when Hill premiered its now iconic video, a diptych presenting the singer (then pregnant) as both latter day street bohemian and retrofied Spector-esque fashion plate in a zebra-striped dress and bobbed hairdo. The song and video captured pop audience's imaginations the summer of 1998, scoring perputual airplay and #1 spot on the Billboard Hot 100. Animal prints soon crept from runways onto the backs of other singers. The next year, "Doo Wop" swooped up four VMAs, including the coveted Video of the Year prize.

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Britney Spears, ‘…Baby One More Time’ (1998)

Filer under: the quintessential teen pop video, regardless of era. Also: one of the most tantalizing song compositions to feature a piano riff, and certainly the only one with lyrics euphemizing puppy love as bondage — those innuendos purred out by a 16-year-old, no less. Most importantly: the serendipitous debut of Miss Britney Jean Spears, the doe-eyed Louisiana moppet who would reign the official teenage dream queen of Y2K pop only a year later. Even if she never released a second single, "…Baby One More Time" was a monster, a history-making hit on both radio and MTV. The song's video popularitywas buoyed significantly by the controversy sparked by Spears' choice of wardrobe: a tarted up school-girl uniform, later revealed to be purchased at K-Mart. The video earned three VMA nominations the following year, winning none. At later points in her career, she bravely pioneered other tricky costume ideas, giving snakes, red cat suits, and diamond-encrusted body stockings a go. But it will always be the school-girl uniform, and "…Baby," that defines the precocious promise of our early love affair with Gen Y's most fiercely adored icon.

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TLC, ‘No Scrubs’ (1999)

Continuing the  futurist visual plight of Michael and Janet's "Scream" video,  TLC's "No Scrubs" was a Hype Williams-helmed tour de force. The year was 1999, and every act was doing their best to appear "modern," but no other mainstream group took it to TLC's level. Chili, T-Boz, and Left-Eye are decked out in resplendent wigs and their finest space-age apparel, remembling Japanese cyber-punk heroines as they traverse a severely white universe divided up into three thematic microcosms, all seemingly sponsored by Ikea in the year 2050. The clip won instant accolades for its clever execution, earning 6 VMA nominations in 1999, and winning Best Group Video.

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Christina Aguilera, Lil’ Kim, P!nk, Mya, ‘Lady Marmalade’ (2001)

For their Moulin Rouge! themed remake of LaBelle's classic "Lady Marmalade," Christina Aguilera, Lil' Kim, P!nk, and Mya had to play the cards they were dealt: when singing about the exploits of a heroic New Orleans tramp, you do as Mlle. Marmalade does — you gussy up in lingerie. They all managed to put their own unique twist on the negligee lace and garter belt prototype, with P!nk keeping her signature hair shade, Mya looking like a 20s era Pigalle coquette, Lil' Kim defying all conventional boudoir reference points, and Christina Aguilera concurrently trying them all on for size. This is the video some remember caustically as Xtina's "Dee Snider" moment, but even haters could not deny the enormity of the song, which landed majestically at #1 on charts on both sides of the Atlantic, where it remained for a generous part of the summer. In September, it won Video of the Year and Best Video from a Film at the VMAs.

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No Doubt, ‘Hey Baby’ (2001)

Wherein a 32-year-old Gwen Stefani tries on dancehall, houndstooth, grafitti, fishnet, and pigtails for size — and pulls it off with charm. No Doubt quickly brushed off the dismaying chart performance of 2000's  Return of Saturn by releasing Rock Steady, a hedonistic record fueled by their recent obsession with Jamaican party music, Prince, and U.K. electropop. To suit the sound overhaul, the band's image had to undergo its own makeover. The result was dizzying: customized band logos (influenced by the graffiti of Stephen Sprouse), houndstooth and argyle patterns (a nod to British mod and Two-tone prep), and a ton of red, yellow, and green (traditional Rasta hues) swiftly defined the look of No Doubt in their feel-good renaissance. All motifs are present and accounted for in "Hey Baby," the band's comeback single and video, which won two VMAs in 2002 for Best Pop and Best Group Video.