Which VMA Video Of The Year Winner From The Last 20 Years Is The Most Timeless?

The 2013 MTV Video Music Awards are set to air this Sunday night, August 25, beginning at 9/8C. Although the spectacle of the event now outweighs the actual awards themselves, the pinnacle of the evening still revolves around which artist gets to take home the coveted Moonman for Video Of The Year. With that in mind, we thought we’d take a look back at the winners of the prizeover the last 20 years—including acts like Beyonce, Eminem, Pearl Jam and more!—to determine which videos have withstood the test of time and which were mere flash-in-the-pans. (We repeat, which VIDEOS, not which ARTISTS or which SONGS; our list is purely built around how well the videos themselves hold up.)

With that in mind, please enjoy our countdown of the Most Timeless VMA Video Of The Year Award Winners Of The Last 20 Years.

20 . VIDEO: Panic! at the Disco, “I Write Sins Not Tragedies”
YEAR: 2006

The less said about this video in particular (not to mention this era of music videos), the better. The line-up of videos during this year was very, very weak; the other nominees were Christina Aguilera (“Ain’t No Other Man”), Madonna (“Hung Up”), Red Hot Chili Peppers (“Dani California”), and Shakira (“Hips Don’t Lie”). Not really a memorable video in the bunch, truth be told, but this Panic! selection was extremely embarrassing not only on that night, but 10,000 times more so in retrospect.

19. VIDEO: Britney Spears, “Piece of Me”
YEAR: 2008

Awarding Britney Spears with the Video Of The Year award for a total garbagesauce production like “Piece Of Me” is the equivalent of a those mushy moments at the Academy Awards when very old people who have never won an Oscar receive a Lifetime Achievement Award for their body of work. Britney had never won the big prize at the VMAs until “Piece Of Me,” which is really a shame considering we could rattle off about a dozen of her videos off the tops of our heads that are more memorable than this one.

18. VIDEO: Christina Aguilera, Lil’ Kim, Mýa and P!nk, “Lady Marmalade”
YEAR: 2001

Who gets the lion’s share of the blame for this disaster? It’s a toss-up between director Baz Luhrmann (who commissioned the track for his otherwise awesome film Moulin Rouge!) and Missy Elliott, the song’s producer. This video featured tons of 2001 firepower, but it has not aged well, especially when you consider it beat out the far more deserving likes of Missy’s own “Get Ur Freak On”, Fatboy Slim’s “Weapon Of Choice” and U2’s “Beautiful Day.”

17. VIDEO: Green Day, “Boulevard of Broken Dreams”
YEAR: 2005

There’s no sense in arguing that American Idiot is anything other than one of the best and most important albums of the 2000s, but we don’t exactly feel comfortable describing this video as “memorable.” If you, like us, didn’t remember this video, we’ll refresh your memory: It consisted of the members of Green Day walking on a treadmill (and occasionally playing their instruments) in front of a green screen for four minutes and 38 seconds. NEXT!

16 and 15. VIDEO: Eminem, “The Real Slim Shady” and Eminem, “Without Me”
YEAR: 2000 and 2002

Make no mistake, Eminem is one of the most dazzling lyricists in the history of hip hop, but his videos definitely have not aged well. In particular, this pop culture skewering “The Real Slim Shady” (from the height of the TRL era) features cameos by Kathy Griffin and Fred Durst and an extended sight gags revolving around Tom Green’s all-but-forgotten “The Bum Bum Song.” For what it’s worth, “Without Me” is a better video, but is still burdened with of-the-moment references (Moby, The Real World cast, Jenna from Survivor!!!) that age worse than a bottle of wine left out in the sun.

14. VIDEO: Rihanna (featuring Jay-Z), “Umbrella”
YEAR: 2007

“Umbrella,” the song, is undeniable. The video, though, is largely forgettable save for one fantastic moment. Near the conclusion of the Chris Applebaum directed video, Rihanna stands underneath an umbrella while a rainstorm of electric sparks rains down from the heavens. It’s a lasting image, and remains the moment that transformed RiRi from a likable pop star into an international icon.

13. VIDEO: OutKast, “Hey Ya!”
YEAR: 2004

Ok, now we’re starting to get into the GOOD videos. “Hey Ya!” was one of the most ubiquitous songs of the mid-Aughts, and the video featuring multiple versions of Andre 3000 performing on an Ed Sullivan-esque variety show is memorable. However, it does feel a bit derivative of Lauryn Hill’s “Doo Wop (That Thing),” which is coming up on our countdown!

12. VIDEO: The Smashing Pumpkins, “Tonight, Tonight”
YEAR: 1996

The Smashing Pumpkins felt like the most important band in the world when they released their mammoth double LP Mellon Collie & The Infinite Sadness back in 1995. With their arena rock chops and ambitious artistic vision, they seemed poised to be the next U2. Little did we know at the time, they spent all of their creative capital on this project and were never able to achieve this level of success again. In particular, the video for “Tonight Tonight” feels timeless and, at the same time, very much of its era.

11. VIDEO: Lauryn Hill, “Doo Wop (That Thing)”
YEAR: 1999

Speaking of people who were poised to be the Next Big Thing but promptly fell off the map, Lauryn Hill’s legacy is one of the saddest of all. Currently serving time in state prison on tax evasion charges, the world was Hill’s oyster when she dropped The Miseducation of Lauryn Hill on the heels of the worldwide fame she garnered as a member of The Fugees. “Doo Wop” is a timeless track, and an equally timeless video that was a direct influence on future Video Of The Year award winners like Outkast’s “Hey Ya.”

10. VIDEO: Katy Perry, “Firework”
YEAR: 2011

While only time will tell how long Katy Perry’s reign as a pop queen will last, her collaboration with esteemed director Dave Meyers is one for the ages. Its overtly empowering message will ensure airplay for years and years to come, but as far as the video is confirmed, who is ever going to forget this image? NO ONE, that’s who!

9. VIDEO: Madonna, “Ray of Light”
YEAR: 1998

A full 12 or 13 years before EDM became a staple on the pop charts and molly became the drug of choice, the always experimental Madonna teamed up with William Orbit on a track that was the sonic embodiment of the ecstasy craze of the time. Visionary music video director Jonas Akerlund seemed to have a strong grasp of both the spiritual themes of the song and its hedonistic feel, and through the course of the video, transformed Madge from an earth mother into the life of the rave.

8. VIDEO: Rihanna (featuring Calvin Harris), “We Found Love”
YEAR: 2012

What “Ray Of Light” was to 1998, “We Found Love” was to 2012. However, the key twist that makes this a memorable video is that director Melina Matsoukas spends just as much time showing the aftereffects of hedonistic behavior and bad romance as she does portraying them as “fun.” In fact, we’re still kind of shocked at how “dark” this video gets, and the grimy places that it shows. History will look back at this video with increasing fondness as the years progress, trust you me.

7. VIDEO: Aerosmith, “Cryin'”
YEAR: 1994

The only thing standing in the way of Aerosmith and Alicia Silverstone being our favorite combination of things of all-time is how delicious peanut butter tastes when paired with jelly. “Cryin'”, directed by Marty Caliner, was the first of three videos to feature Alicia as a protagonist, the other two being “Crazy” and “Amazing.” We’ll admit that, in retrospect, this video DOES feel a little ’90s, but how can you deny the legacy of a music video that ends with an image like this?

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