By the time the 2010 MTV Video Music Awards wrap up late Sunday night, a total of 16 awards will be handed out to the various winners at the show. The most coveted Moonman is, of course, the prize for Video of the Year, the clip that personifies the height of music video greatness for the past 12 months. This year's crop includes six well-deserving nominees, including B.o.B's "Airplanes," 30 Seconds to Mars' "Kings and Queens," Florence and the Machine's "Dog Days Are Over," Eminem's "Not Afraid" and a pair of clips from Lady Gaga ("Bad Romance" and "Telephone"). No matter who wins, the victor will join an exclusive club that contains some of the biggest artists of the past three decades (including Madonna, Britney Spears, Eminem, Aerosmith, Green Day, Van Halen and Sinéad O'Connor).

But no awards show is perfect. The Academy of Motion Picture Arts and Sciences has handed out Oscars for Best Picture to the likes of forgettable afterthoughts like "Shakespeare in Love," "Crash," "Kramer vs. Kramer" and "Chicago." The dudes from Steely Dan have a Grammy for Album of the Year for Two Against Nature. "Everybody Loves Raymond" won a pair of Emmys for Outstanding Comedy Series. There are always some missteps, and the MTV Video Music Awards are not immune to them. So check out the list below of all of the clips that have won Video of the Year, ranked from the most regrettable to the absolutely indisputable.

Jamiroquai, "Virtual Insanity" (1997)

Had the concept of viral video been around in 1997, Jamiroquai's "Virtual Insanity" would have become a much-passed-around hit and then would have vanished within three days (sadly, home use of the Internet was still pretty nascent). It's visually interesting in a how'd-they-pull-it-off? sort of way, sure, but both the band and the song have fallen completely by the wayside as far as relevance is concerned. The winner in 1997 probably should have been Beck's "The New Pollution" or No Doubt's "Don't Speak."

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Neil Young, "This Note's For You" (1989)

Neil Young is great -- a living legend if there ever was one. But does anybody remember anything about any of this?

The Cars, "You Might Think" (1984)

No disrespect to the Cars, but this somehow beat Michael Jackson's "Thriller." Argument over.

Don Henley, "Boys of Summer" (1985)

It was a big deal in '85, though Henley's caché has faded in the quarter-century since his victory. "Boys of Summer' feels vaguely nostalgic, but mostly it just kind of sits there.

INXS, "Need You Tonight/Mediate" (1988)

Has any band suffered a greater fall in history than INXS? They were literally the biggest band in the world for a stretch run at the end of the '80s, yet they never got a big comeback or even an shot at ironic cult status. It's a shame, because most of their back catalogue is stunning, though "Need You Tonight" is a pretty weak video in their collection.

Sinéad O'Connor, "Nothing Compares 2 U" (1990)

You have to give O'Connor props for this video, which is literally just a static shot of her face, but even now it's sort of hard to sit through (not because it's bad, but because it's uncomfortably honest). Plus, this should totally have lost to Madonna's "Vogue," which was also nominated in 1990.

Christina Aguilera, Lil' Kim, Mya and Pink, "Lady Marmalade" (2001)

It was awesome at the time and still looks pretty hot, though "Lady Marmalade" loses points for being a cover and also for being associated with "Moulin Rouge."

Van Halen, "Right Now" (1992)

Another interesting concept that was then parodied into oblivion and doesn't hold up as well today. This video would have been at least 73 percent more awesome if David Lee Roth had been involved (though that's sort of true of all music videos, really).

Dire Straits, "Money for Nothing" (1986)

The animation is obviously dated though still retains some of its trippiness. However, this had to have won simply because it has the "I want my MTV" line in it, right?

Aerosmith, "Cryin'" (1994)

Aerosmith have always made great videos, but "Cryin'" is probably the weakest of the collection that came out of Get a Grip (including "Crazy" and "Livin' on the Edge"). Still, that money shot at the end is pretty solid.

R.E.M., "Losing My Religion" (1991)

This clip was inexplicable when it debuted and still looks pretty odd today. Full of art school nods, strange lighting and mandolin solos, "Losing My Religion" is one of the odder ducks in this particular club but picks up points because it very much foresaw the alternative revolution that would rule the VMAs throughout the early '90s.

Britney Spears, "Piece of Me" (2008)

There's nothing wrong with "Piece of Me," but it ends up at the middle of the pack only because Spears has so many other amazing videos that are clearly superior to this one. When Spears won in 2008, it was just like when Scorsese finally won Best Picture for "The Departed."

Eminem, "Without Me" (2002)

See above, though this is mainly here because "The Real Slim Shady" -- Eminem's other Video of the Year winner -- is so much better.

Panic! at The Disco, "I Write Sins Not Tragedies" (2006)

A left-field choice that still looks like nothing else in music videos, Panic! at the Disco crashed the party with their weird emo art songs but proved they belonged there.

The Smashing Pumpkins, "Tonight, Tonight" (1996)

A grand cinematic vision for just as epic a song, "Tonight Tonight" still looks pretty amazing today and also gets bonus points for sending the careers of Jonathan Dayton and Valerie Faris (the pair behind "Little Miss Sunshine") into the stratosphere.

Madonna, "Ray of Light" (1998)

Madonna finally won in 1998 after being denied for years, and she couldn't have picked a better time to do it. "Ray of Light" still feels ahead of its time 12 years later, and the impossibly kinetic clip remains an incredible visual accomplishment.

Green Day, "Boulevard of Broken Dreams" (2005)

This was an example of the right video for the right song at the right time. Few things captured the zeitgeist the way "Boulevard of Broken Dreams" did, and it remains a great example of what it was like to live in America in 2005.

Rihanna, "Umbrella" (2007)

Only "Hey Ya" dominated the pop culture landscape more this decade, so even though there were other videos nominated in 2007, this was never a competition.

OutKast, "Hey Ya" (2004)

See above.

Lauryn Hill, "Doo Wop (That Thing)" (1999)

Lauryn Hill got everything right with her solo album, including this video. The split-screen effect creates just enough disorientation to demand multiple viewings, and those second and third times around are rewarded with new details and incredible cinematic panache.

Missy Elliott, "Work It" (2003)

Nobody does a visual buffet like Missy, and this video features super-cool dancing, strange effects, a drop-in from Timbaland and some crazy bees. What's not to love?

Eminem, "The Real Slim Shady" (2000)

It's the best statement of purpose the most important musician of the 21st century has produced. Of course it had to win.

Beyoncé, "Single Ladies (Put A Ring On It)" (2009)

Kanye wasn't wrong.

TLC, "Waterfalls" (1995)

"Waterfalls" had everything: A great series of narratives, a groovy song, cool special effects and a message.

Peter Gabriel, "Sledgehammer" (1987)

While the animation for "Money for Nothing" has faded over time, the clay-fueled pyschedelia of Gabriel's clip is still pretty mindbending today. It's thought by many to be among the best music videos ever made, and like some of those other greats ("Thriller" and "Smells Like Teen Spirit" among them), it only seems to get better with age.

Pearl Jam, "Jeremy" (1993)

With its deep narrative, art school images and shocking finale, "Jeremy" was so good that Pearl Jam quit making videos for almost a decade. Not only did "Jeremy" accomplish everything a music video is supposed to do (give the song a narrative, show what the band represents, advertise the album), but it also created a conversation around violence in schools and the psychological complications of childhood. Too good to be ignored, "Jeremy" is the best video to ever be awarded the Moonman for Video of the Year.

What do you think the biggest Video of the Year hits and misses are? Let us know in the comments!

The 27th annual MTV Video Music Awards will be broadcast live from the Nokia Theatre in Los Angeles on September 12 at 9 p.m. ET.