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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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Michael Jackson, ‘Thriller’ (1984)

Not only the most famous music video ever made, this spellbinding cinematic vehicle showcases Michael Jackon's incomparable style at its peak. Even zombified, he exudes a deathly cool swagger in cropped pants, white socks, loafers and iconic custom miltary jacket, which went up for auction recently. Surprisingly, despite its immortal status nearly 30 years later, "Thriller" didn't win Video of the Year that honor went to the Cars. However, it did pick up Best Choreography and the all-important Viewer's Choice Award.

By Colleen Nika

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Madonna, ‘Like a Virgin’, (1984)

Madonna's performance of her seminal hit at the 1984 VMAs is one of the most iconic live moments in the awards show's history, and the perfect complement to its equally famous nuptially-themed video. Even though it didn't win any awards at the VMAs the following year (despite three nominations), the "Like A Virgin" video ensured that bridal style would never be the same. Britney Spears' and Christina Aguilera's reenactment of the look during their onstage tryst with Madge, nearly two decades later in 2003, only reinforces the clip's legendary style, and cultural status.

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The Eurythmics, ‘Sweet Dreams’ (1984)

Annie Lennox and Dave Stewart's sharp-suited looks certainly encapsulate  New Wave androgyny, but the style impact of "Sweet Dreams (Are Made Of This)" isn't just about how eccentric British synthesists were dressing in '84, a particularly memorable VMA year. Here you enter a surreal fantasia, a kinky but stoic exploration of weird technology, power plays, boating, and, yes, that inscrutable cow — the best non sequitur of any 80s video (and there were many.) In a victory history would prove judicious, "Sweet Dreams" won Best Video By A New Artist that year.

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A-Ha, ‘Take on Me’ (1985)

This clip is sterling proof that style doesn't require an actual human presence — dizzying illustrations of a perfect man, like fashion drawings reified, will suit just fine. But what a male: a-Ha's resident Norwegian dreamboat Morten Harket held all the attributes of the exemplary 80s American-bred pop star: leather jacket, jeans, a wafting hairstyle just buoyant enough to keep Aquanet afloat. Yup, it's all here — and exquistely rendered by director Steve Barron in a pioneering "rotoscoping" technique. MTV awarded the achievement with six VMAs — Best New Artist in a Video, Best Concept Video, Most Experimental Video, Best Direction, Best Special Effects, and Viewer's Choice.

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Siouxie and the Banshees, ‘Peek-a-Boo’ (1989)

Most of Siouxsie and the Banshees' 80s material was too dark for the VMAs to digest, let alone nominate, even when blackhearted British pop could feasibly find daytime airplay love from MTV. But by 1989, the gothic rock pioneers were going through a decidedly palatable phase. "Peek-A-Boo," an oddball slice of pop featuring cheeky lyrics (sample: "Flaccid ego in your hand"), accordian, cowbell, and a taunting chorus based on a chilling 1938 jazz standard, became a career-expanding hit, creeping up to #1 on the Alternative chart. Best of all, its accompanying video ionized all the hallmarks of Siouxsie's trademark style into one neat horror-pop peepshow package. The payoff? A nomination for Best Post Modern Video alongside fellow shadow players The Cure and Love & Rockets.

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George Michael, ‘Freedom’ (1990)

The was the video that proved George Michael was big enough to afford Linda Evangelista (she of the famed $10,000 per day working rate), and confirmed that supermodels like Evangelista, Naomi Campbell, Tyra Banks, Christy Turlington, and Cindy Crawford were commanding enough names (and faces) in 1990 to fully replace the iconic British singer in his own video. The attractive gimmick worked well enough to become a major radio and MTV hit, racking up five nominations at the 1991 VMAs. Though it didn't win those awards, it's an aesthetic  high point in the pantheon of fashion and music marriages of convenience.

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Madonna, ‘Vogue’ (1990)

Even the Queen of Pop's naysayers have to concede this clip is the epitome of "glam." It was the official debut of Madonna's classic Gaultier cone-shaped bra, as well as a precursor to her "Blonde Ambition" tour look that manifested in a combustible dialogue about sex and pop and the 90s. Directed by David Fincher, and filmed in black-and-white, "Vogue" channeled the visual legacy of Art Deco artist Tamara de Lempicka, and paid style and cinematic homage to the song's lyrical heroes and heroines (Greta Garbo, Marilyn Monroe, Marlon Brando, Joe DiMaggio). The mass result? A new generation of MTV viewers discovered the merits of Betty Davis eyes. The Madge result? Nine VMA nominations, three of which she won.

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Aerosmith, ‘Cryin” (1993)

Though her role two years later in Clueless made her a teen superstar, Alicia Silverstone's cameos in Aerosmith's "Cryin'" and "Crazy," alongside rock progeny Liv Tyler, made her Gen X's barely legal pin up of choice. Plus, her style choices for said videos laid the groundwork for the success of Britney Spears' beguiling "…Baby One More Time" with Millenials only five years later, proving that precocious girls + crop tops, schoolgirl kilts, and truancy = a failproof combination, illusory generational divides be damned.

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Björk, ‘Human Behaviour’ (1993)

Björk's first major solo hit, produced by Nellee Hooper, introduced her as a seminal new talent for avant-pop. Its Michel Gondry-directed video crystallzied the Icelandic genie's agenda with an immortal visual and obliterated expectations for what a promotional clip could be in 1993. "Human Behaviour" is a paper-mache fantasia presenting Björk in a demented version of Goldilocks and The Three Bears; her journey includes a jaunt to the moon and concludes, endearingly, in a bear's stomach. Throughout, she wears a silver lame dress, a look other singers, including Madonna, would soon be shadowing. The video received VMA nominations 1994 including Best Female Video and Breakthrough Video, but took home none. No matter: the birth of a new aesthetic icon ensured a lifetime of visionary videos ahead.

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Michael and Janet Jackson, ‘Scream’ (1995)

Continuously upping the game when you've already set so many cultural milestones in place can't be easy, but Michael Jackson was determined to go for broke with 1995's "Scream," his collaboration with sister Janet that, at $7 million, was the most expensive music video in history. Set in a dystopian future, the black and white Mark Romanek-directed clip features the power siblings on a spaceship, gesticulating aggressively in matching leather pants and ruffled tops. "Scream" also stylishly assembled a variety of pop references from across the bow, including anime, Akira, and Andy Warhol and Jackson Pollack works. The video received constant airplay on MTV and received 11 VMA nominations that year, winning three. The video remains one of the most memorable in pop history, lauded both for its obvious trendsetting production values and its mastery of themes of power and defiance. It's withstood the litmus tests of time: 16 years later, this is still The Video to Beat.

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Smashing Pumpkins, ‘Tonight, Tonight’ (1995)

This is the video where Billy Corgan, D'Arcy Wretsky, and James Iha became immortal thanks to a grandiouse, time-warping trip 20,00 leagues under the sea (and to the moon and back). The Smashing Pumpkins were already the most popular rock band in America by 1995; this video, directed by medium-defining vanguards Jonathan Dayton and Valerie Faris, confirmed the extent of their imaginative scope. Influenced by the 1902 silent film, A Trip To The Moon, "Tonight, Tonight" showcases the Pumpkins in ghoulish Victorian finery, cementing their most elegant and iconic visual in a catalogue defined by the precipice of glamor and grunge, amongst other juxtapositions. The video went on to win six VMAs in 1996, including Video of the Year, and still is regarded as one of the pivotal moments in music video history.

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Prodigy, ‘Smack My Bitch Up’ (1997)

Iconic for its bracing connotations of hard living and harder partying, "Smack My Bitch Up" is Prodigy's ultimate post-rave anthem for the young, eager, and reckless. Suitably, its paralyzing video remains one of the most polemic video clips in history, and was banned from daytime airplay nearly universally. Jonas Åkerlund (also Madonna's late 90s videographic guru of choice) kept the narrative premise simple: track an anonymous hedonist's solo path of ecstasy, chaos, and destruction; insert wanton scenes of drug use, kinky sex, and nudity; shock with a big reveal (spoiler: the perp is a woman!) at the end. It's exhausting to behold, and a victory for any film. But it also manages to convey style on the street (and the vices that drove it) better than any fashion ad could. Despite its outlaw status (or, indeed, partially because of it?), the video fared at well at the 1998 VMAs, scoring Best Breakthrough Video and Best Dance victories.

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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.

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White Stripes, ‘Seven Nation Army’ (2003)

Among the fashion rules The White Stripes regularly disobeyed: dressing uniformly in red (regardless of season), the general laws of black hair dye, and that unspoken rubric about not dressing in the same outfit as your sister, er, wife. But with "Seven Nation Army," the blues rock duo proudly proved an old Wive's expression true: "red on black is a friend of Jack."  The Alex and Martin-directed clip feature Jack and Meg situated inside an infinite tricolored, triangular kaleidoscope of surreal imagery. The 2003 single truly put The White Stripes on mainstream turf, earned them critical acclaim, and landed them four VMA nominations and one win (for Best Editing).

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Beyonce, ‘Crazy in Love’ (2003)

For Beyoncé's official coming out party, she pulled out the big guns, hiring Rich Harrison to produce, future husband (and now father-to-be) Jay-Z to rap, and Jake Nava to direct its vivacious video. Only 21 at the time, the singer celebrated her foray into adulthood and independence by channeling an icon – James Dean. "I wanted to be a female version of [him] and wear an iconic white T-shirt and jean shorts," she told W this year. Red pumps, now a part of pop visual history, were the perfect complementing piece – B jokes that dancing in them was the ultimate victory, though we suspect the outrageous success of her debut single – Number One just about everywhere, the most acclaimed single of the year, one of the decade's defining hits — felt pretty nice, too. VMA recognized Beyonce's sterling solo effort by awarding it three VMAS — Best Female Video, Best R&B Video, and Best Choreography.