9. Britney Spears – "Piece of Me" (2008)
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The "Piece of Me" video isn't that bad on its own. The problem is "Piece Of Me" isn't anywhere near as good as the Britney videos that didn't win the top prize. Seriously, the pop star has had so many pop culture-defining videos, and "Piece of Me" is the only one to win Video of the Year?! It's just sad. Considering that genuinely iconic clips like "...Baby One More Time," "I'm A Slave 4 U," "Toxic," and "Me Against The Music" failed to win a Moonman for Video Of The Year, giving it to "Piece Of Me" seems more like MTV apologizing for never giving Britney the top prize than anything else.
What Should Have Won: The Ting Tings – "Shut Up and Let Me Go"
8. Rihanna – "Umbrella" (2007)
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Like "Piece of Me," the "Umbrella" music video isn't a disaster. It's just sort of unremarkable. For most of us, this video served as our first introduction to Rihanna. Maybe it only looks a little on the dull side because in the eight years (woah) since the video was released, Riri has proven herself capable of vastly more complex and interesting things. Put this video next to the one for "Bitch Better Have My Money" and there's really no comparison.
What Should Have Won: Justice – "D.A.N.C.E."
7. Eminem – "The Real Slim Shady" (2000)
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While some of Eminem's output has stood the test of time, most of his early singles sound pretty dated. Combine that with a video that's sole purpose is to make fun of as many 2002 references as possible and you get a Video Of The Year winner that hasn't aged anywhere near as well as its competition. Honestly, it's kind of shocking to see how poorly Em's "dangerous" persona as America's Biggest Rapper and Your Mom's Worst Nightmare has aged. The whole thing seems silly now.
What Should Have Won: 'N Sync – "Bye Bye Bye"
6. Green Day - "Boulevard of Broken Dreams" (2005)
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This video is basically just Green Day slowly walking around with their hands in their pockets while staring at the ground. Sound familiar? That's because the band did the same thing (but better) 11 years before in their video for "When I Come Around."
What Should Have Won: Gwen Stefani – "Hollaback Girl"
5. Neil Young – "This Note's For You" (1989)
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Where do we start with this video? I guess let's start at the top.
1. A neon beer sign: Forever a beacon that what you're about to see will likely suck.
2. Oh no! A saxophone!
3. Wait is this a beer commercial?
4. Why drunk are all these girls gazing longingly at Neil Young?
5. Neil Young's band has seven saxophones in it. The '80s were surreal.
6. Is this making fun of beer commercials by being a beer commercial?
7. Michael Jackson!
8. Michael Jackson's on fire!
9. Neil Young is killing Michael Jackson!
And that's just the first half of this trainwreck.
What Should Have Won: Madonna – "Like a Prayer"
4. Aerosmith - "Cryin'" (1994)
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WTF.
What Should Have Won: Beastie Boys – "Sabotage"
3. The Cars – "You Might Think" (1984)
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Apparently the special effects in this video were pretty incredible back in the mid-80s. Or at least, that's what people who were watching MTV 30 years ago say. That said, "You Might Think" isn't being penalized just for looking extremely cheesy in 2015. Instead, its major offense is beating out the groundbreaking video for "Thriller," which many still point to as integral to the evolution of music videos as an art form. We don't blame The Cars, but we do blame MTV.
What Should Have Won: Michael Jackson – "Thriller"
2. Miley Cyrus – "Wrecking Ball" (2014)
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Yes, Miley fans. This ranking might seem pretty blasphemous, but hear me out: 10 years from now, who knows what we'll think of Miley's career. Maybe she'll be a funny anecdote we bring up when waxing poetic about our confusing early 20s. Maybe she'll mature with us, and be the biggest, most critically adored pop star in history. But one thing is certain: We will always laugh when we talk about her crying while swinging around naked on a giant wrecking ball. Sorry, but that's the truth.
What Should Have Won: Sia – "Chandelier"
1. Van Halen – "Right Now" (1992)
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Like a awkward middle-schooler searching for meaning by reading the instructions on his can of AXE body spray, America made an extremely cringeworthy transition from hair metal to grunge in the early '90s.
It's appropriate then that 1992 found the video for Van Halen's "Right Now," perhaps the least subtle thing in the world, squaring off against Nirvana's stripper/cheerleader-laden "Smells Like Teen Spirit" for the VMAs' top prize.
Right now, it's more clear than ever that the wrong video won. Right now, you're reminded of Van Halen's Sammy Hagar years and woefully depressed. Right now, you're watching the worst Video Of The Year winner ever.
What Should Have Won: Nirvana - "Smells Like Teen Spirit"