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2001: The pop star gives a sneak peek of her not-that-innocent look in a peekaboo lace mini and strappy sandals before hitting the MTV stage to perform "I'm a Slave 4 U" with a 7-ft. python draped around her shoulders.
2002 The next year, Spears says "Bye Bye Bye" to boyfriend Justin Timberlake and makes it clear she's also officially ditched the squeaky-clean image with a dominatrix-inspired ensemble.
2008: After a disastrous performance at the 2007 VMAs, Spears makes a triumphant return, stepping out in sparkling vintage Atelier Versace to pick up three Moonmen awards.
2011: Spears revisits the leather, sequins and boots of past ensembles, in a signficiantly more muted way.
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2004: Hot on the heels of her solo success, the star sports a golden bejeweled suit that is short on fabric, long on baring her sexy legs.
2006: Two years later, the singer goes red carpet glam in Atelier Versace, Lorraine Schwartz diamonds – and a hint of her signature sass.
2009: It's legs back on display for the "Single Ladies (Put a Ring on It)" star, who opts for a plunging Roberto Cavalli minidress, black pumps and big statement earrings to pick up three Moonmen, including top honors for Video of the Year.
2011: Previous ensembles couldn't compare to the jaw-dropping impact of Beyoncé's sophisticated orange Lanvin gown, which plays an integral part in her onstage baby announcement.
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2009: It wouldn't be an awards show without a few Lady Gaga wardrobe changes – but of all the looks this year, it was the face-shrouding lace number that launched a thousand Halloween costumes.
2010: The avant-garde pop star pays tribute to Alexander McQueen in appropriately over-the-top fashion, pairing his glam creation with dip-dyed hair and a golden Mohawk.
2011: Lady Gaga doesn't make an appearance at the show, but her alter ego Jo Calderone does.
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2001: Part biker babe, part newsboy, all questionable: the singer's debut ensemble at the VMAs definitely does its job, which is to get the newbie songstress on everyone's radar.
2004: A few years later, Keys shows her softer side, gliding down the Miami carpet in a lacy, gilded gown.
2009: It becomes clear the star is hitting her stride. She wears this dotted black mini, fierce heels and a slicked-back bun, a look that feels truest to the star's funky style.
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2003: In case you'd forgotten her name, the singer sports it down the side of her capri track pants – which coordinate perfectly with her bleach-streaked ponytail and workout gear.
2005: Losing the name tag, but still going for attention-grabbing attire, Fergie channels her inner flamenco dancer in a lemon-lime Rami Kashou creation.
2006: No ruffles, no sweats and no chunky highlights. Fergie Ferg keeps things simple and sexy, though she holds fast to the heavy eyeliner and funky hair that look so good on her.
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2008: Perry's breakout single "I Kissed a Girl" is hot on the charts – but even hotter? The singer's 1940s-inspired halter-and-hot pants ensemble, which plays up her cheeky pinup image to a tee.
2009: A year later, the singer kisses retro goodbye for a futuristic, sparkly mini by The Blonds and coordinating pumps.
2010: One month before tying the knot with naughty Brit Russell Brand, Perry flaunts her wild streak, pairing her Technicolor hair with a Marchesa mini that makes her feel, she says, like an ice skater.
2011: She gives the cutesy costumes a year off, but in 2011 she jumps back into the wacky wardrobe well in an Asian-inspired Atelier Versace number with a matching parasol.
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2006: A newcomer on the music scene, Jay-Z's 18-year-old protégé shows off her ingenue style in a flirty white dress and long, curly locks.
2008: What a difference two years make! Crediting her cropped hair for transforming her style, the pop star goes edgy with her look, pairing her Patricia Field bustier with white T-strap Cesare Paciotti pumps.
2010: Continuing to push the fashion limits, the singer takes the plunge in a gold halter dress – all the better to show off her flaming red hair.
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2000: Pink plays up her name – and her tough-girl image – with shocking spiked hair and a wild DampG floor-length coat that tie into the message of her debut album, Can't Take Me Home.
2002: Who's Missundaztood? The punked-out artist, whose stripes, swirled body art and combat boots take her look over the edge.
2008: Recently split from (now back on-again!) hubby Carey Hart, the star is a singular sensation in a flowing striped Alexis LaMontagna gown, Neil Lane jewels and silver locks.
2009: A year later, the singer is clearly in good fashion company in a Balmain mini and Siera diamonds – Shakira wears the same dress that night!
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2005: The College Dropout artist graduates with top honors, wearing a jazzy white tuxedo jacket and metallic aviators to pick up his Best Male Video award.
2008: Dressed in a sharp but conservative suit, the ever-controversial West lets the backdrop of fireworks close out that year's show with a bang during his performance of "Love Lockdown."
2010: A year after his Taylor Swift debacle, the risk taker looks fired up to return to the VMA stage dressed in head-to-toe red.
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2000: Jenny from the Block arrives on the arm of then-beau Diddy in a belly-baring white ensemble and Fly Girl-esque bandanna.
2001: Debuting a new man (husband No. 2 Cris Judd) and a new look, the star goes Miami chic and über-sexy in a leopard-print top and thigh-high boots.
2006: Newly wed to now-ex Marc Anthony, the diva glitters from head to thigh in a turban and matching minidress.
2009: It's back to body-conscious dresses for the star, who wears Louis Vuitton accented with Lorraine Schwartz jewels and Christian Louboutin shoes.
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2002: The singer is appropriately "Dirrty," showing so much skin in a denim micromini and teeny halter that host Jimmy Fallon describes the look as "boobs wrapped in a napkin."
2003: Aguilera makes it through the wilderness in a flurry of pink feathers before hitting the stage to perform a medley of "Like a Virgin" and "Hollywood" with Madonna and pop rival Britney Spears.
2006: After skipping the show in '05, Aguilera channels old Hollywood in an elegant beaded gown accented with Marilyn Monroe-inspired curls and oodles of jewels for her comeback.
2008: Two years later, the new mom continues to show herself to be a class act, bringing the drama in a Roberto Cavalli mermaid dress and bold Stephen Webster jewels.