The Most Stylish VMA-Nominated Videos

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.

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.

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.

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.

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.

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.

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.

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.

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.

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).

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.

This is certainly Outkast's most incandescent video statement — no small feat, as they've left many in their wake. André 3000 ostensibly funneled inspiration from a melange of sources — A Clockwork Orange,  The Beatles on Ed Sullivan, St. Patrick's Day (hence all the vivid green). He plays eight versions of himself, all members of the fictional group "The Love Below." All are attired in Old Estate chic: argyle, pantaloons, white socks, pinstripes and plaid run rampant throughout. The video reputedly inspired André 3000 to start his own clothing line, Benjamin Brixby, a few years later. For 2004, a Video of the Year trophy, alongside 3 other VMAs and a Grammy months later, provided Outkast all the love they needed to imbibe.

For "Stronger's" robo warrior makeover, Kanye West donned a Rick Owens jacket and chromatic Balmain jeans, along with his new signature: shutter shades. A look few rappers would touch in 2007 has now become synomous with the club-hop scene, indicating just how potently West's stylistic tremors are felt, and echoed, by his peers. But as the rapper would agree, he's more or less unconquerable at his game. As a video statement, "Stronger" stands among the most audacious of the decade, its epic Hype Williams-honed art direction alone qualifying it as a classic. MTV were enthralled by the clip, though their "alternatively structured" award set-up that year precluded it from winning any VMAs.

Thanks to their infamous appearance in 2009's "Bad Romance" video, Alexander McQueen’s legendary 12-inch “Armadillo” heels went from obscenely priced cult item amongst the high-fashion set to dictating a mainstream proclivity for anything claw-shaped. Lady Gaga has that effect on everyone and everything she pulls into her fray; if she loves your work, she'll wear it, and chances are, thousands more peoople will want to wear your work now, too. In 2009, Gaga was McQueen-crazy, brandishing his wares in public, but truly manifesting her fraternal love for the designer with "Bad Romance," an unofficial tribute to McQueen that featured most of his "Atlantis"-themed Spring 2010 looks. The song was the monster hit Gaga had hoped for and still serves as one of the best visual treatises on the now late-McQueen's deep musical impact. It won a slew of VMAs in 2010, including Video of the Year.

In which the usually happy-go-lucky Katy Perry subverts her status as pop's eccentric prom queen by going a little darker, more mature, and, we're not afraid to reaffirm it: alien. Whiffs of t.A.T.u. and a diet version of Nine Inch Nails lace the crawling, industrial-laced production, making its otherwordly success somewhat a surprise. But kudos to its video's fantastical sci-fi extravagance, which feels particularly imperious during an era of spartan promotional budgets. Directed by the avant-gardist Floria Sigismondi (known for Japonais-themed videos with Christina Aguilera, Girls Aloud, Marilyn Manson, and The White Stripes), it's an Avatar level spectacle, with the requisite cyberkinetic style attributes. Thanks to some excellent makeup by artist Kabuki, Perry resembles Na'Vi as Betty Page. Costume designer and stylist Carol Beadle was responsible for her meteoric ensembles, as well as Kanye West's, who guest appears in the video. MTV awarded the video heavy attention, nominating it for five VMAs, where it won Best Collaboration.