How did some of these even get nominated?
Britney Spears – "Piece of Me" (2008)
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"
Rihanna – "Umbrella" (2007)
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."
Eminem – "The Real Slim Shady" (2000)
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"
Green Day - "Boulevard of Broken Dreams" (2005)
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"
