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25 Most Iconic VMAs Moments, From Madonna’s ‘Like a Virgin’ to ‘Miley, What’s Good?’ (Photos)

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A look back at how the MTV Video Music Awards have delivered some of the most famous moments in pop culture history
MTV If the MTV Video Music Awards have ever been about the awards themselves, that era is long past. The most unpredictable and frequently over-the-top awards show remains one of the last-standing watercooler TV events by delivering iconic moments year after year. Here are a few of the most legendary from the show’s 36-year history. MTV Madonna performed her single “Like a Virgin” at the very first VMAs in 1984, donning a wedding dress for a performance that looks downright tame by modern standards but raised a few eyebrows in its day. MTV Looking to top her last performance when she returned to the VMAs stage in 1990, Madonna went for an elaborate 18th Century France-inspired aesthetic for her rendition of Video of the Year nominee “Vogue.” MTV Michael Jackson and then-wife Lisa Marie Presley shocked the audience when they locked lips for an awkwardly long and stilted kiss while introducing the 1994 VMAs. MTV In 1995, Courtney Love crashed Madonna’s live post-VMAs interview by throwing makeup at the pop star and screaming across the room. “Courtney Love is in dire need of attention right now,” Madonna deadpanned before being forced to cede her airtime to the Hole singer’s antics. MTV In hindsight, the idea of Fiona Apple appearing at the VMAs seems like an odd fit, but one suspects it never made less sense to anyone than to Apple herself, who famously proclaimed “This world is bulls—” while on stage to collect her Best New Artist award. MTV Lil Kim’s racy outfit at the 1999 VMAs grabbed the attention of many a red carpet photographer, but the rapper’s one bare breast also captured the imagination of her co-presenter Diana Ross, who couldn’t resist giving Kim’s chest a gentle onstage tap. MTV Upset about his band’s loss to Limp Bizkit, Rage Against the Machine bassist Tim Commerford bum rushed the VMAs stage in 2000, attempting to bring the entire night to a literal crashing halt by scaling the background. He failed and spent the night in jail. Getty Images Former Disney star Britney Spears had no shortage of moments marking her new persona as an adult pop star, but none more iconic than her 2001 performance of “I’m a Slave 4 U” with an albino burmese python named Banana wrapped around her shoulders. Getty Images In 2002, Britney Spears presented Michael Jackson with a lifetime achievement trophy in honor of his birthday, but her use of the phrase “artist of the millennium” seemed to capture Jackson’s imagination, leading him to deliver a speech accepting an award definitely does not exist. Getty Images For decades Madonna stood as the biggest provocateur at the VMAs, and inviting Britney Spears and Christina Aguilera to join her on stage in a re-creation of her iconic “Like a Virgin” performance was meant to be something of a torch-passing.

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