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Lists: Our favorite awkward moments from the VMAs

By Allison Stewart

By Allison Stewart

The most memorable moments at the MTV Video Music Awards aren't the shocking ones - MTV hasn't been genuinely shocking in years - but the awkward ones, the ones involving cringeworthy kisses (Michael Jackson and Lisa Marie Presley, Madonna/Britney/Christina) or, for some reason, men in thongs (Howard Stern, that thing that happened to Eminem that time).

While nothing can top last year's Swift/West I'mma let you finish Olympiad of awkward, Click Track has compiled a list of our other favorite wince-inducing VMA moments. Leave yours in the comments.

5. Justin Timberlake disses "The Hills" girls, 2007

Award winner Timberlake snubbed award presenters Lauren Conrad and company, refusing to either acknowledge their presence or accept his award from them before demanding that MTV play more videos instead of reality shows. Video footage of the encounter seems to have been scrubbed from the internet, but its gracelessness, and Timberlake's unaccountable ungentlemanliness, speaks for itself.

4. Jordin Sparks slut shames, 2008

Sparks divides world into virgins and "sluts," briefly becomes Fox News poster girl.

(Martha and Busta before their convictions, and more, after the jump.)

3. Martha Stewart and Busta Rhymes present an award together, 1997

We can't find video for this, either (we're guessing it's because all existing footage has understandably burst into flames). Basically, Stewart and Busta presented the "Best Dance Video" Award to the Spice Girls after trading really awesome recipes and conducting an in-depth discussion of Busta's stop-time flow. Kidding! Actually, they just bantered awkwardly for a while.

2. Michael Jackson accepts the Artist of the Millennium Award from Britney Spears, 2002

Problem was, the Artist of the Millennium award doesn’t exist. Jackson was actually getting a made-up award, invented to ensure his attendance.

1. Fiona Apple gets award, complains about award, 1997

She lost us at "Maya Angelou."

By Allison Stewart  | September 9, 2010; 11:30 AM ET
Categories:  Lists  | Tags:  Britney Spears, Busta Rhymes, Fiona Apple, Jordin Sparks, Justin Timberlake, Madonna, Martha Stewart, Michael Jackson  
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It's only the malicious press that considers the Jackson/Presley kiss "cringe-worthy." I thought it was sweet, but then I'm not out to destroy anyone with words. Also, you're behind the times. MTV admitted that, yes, they intended to give Jackson the Artist of the Millennium Award. Here's the link. Next time do your research, you hack.

Posted by: SoCalGal2 | September 10, 2010 1:45 AM | Report abuse

Actually, after the ceremony, MTV called the award a misunderstanding. It wasn't until after Jackson died (and you'll note that the date on the link you provided was the day after MJ's death) they pretended they meant to give it to him all along. As for the kiss, we'll just have to disagree on that.

Posted by: Allison Stewart | September 10, 2010 10:06 AM | Report abuse

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