VMA Throwback: What’s The Best “Video Of The Year” Winner Ever?

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This Sunday, Aug. 25, we’ll be watching the MTV Video Music Awards as the 30th “Video of the Year” is announced (where hopefully Macklemore and Ryan Adams take home the big prize). The history of the “Video of the Year” category is pretty spotless, with so many classics taking the top honor every single year. That brings us to today’s quest: a ranking of the best 10 “Video of the Year” winners ever. Try not to lose your religion as we get the numbers exactly right.

10. The Smashing Pumpkins, “Tonight, Tonight” (1996)

If there’s one thing I love in a music video, it’s an homage to ancient cinema. (See: the Fritz Lang fantasia of “Express Yourself.”) This awe-inspiring clip by directors Jonathan Dayton and Valerie Faris (of Little Miss Sunshine) plunks Billy Corgan in the world of the 1902 silent movie A Trip to the Moon, and thanks to some wicked puppetry and cutouts, he looks like a living, colorized version of a turn-of-the-century movie star. Arresting and coolas hell.

9. TLC, “Waterfalls” (1995)

God do I miss R&B trios that came with a message. This legendarily expensive clip gave us T-Boz, Left Eye, and Chilli in liquid splendor preaching about urban issues and chasing the right tributaries (the ones that you’re used to). That metallic, watery sheen is kickass enough, but I think the melodramatic vignettes are handled with just as much care and taste.

8. Beyonce, “Single Ladies (Put a Ring On it)” (2009)

A breakout spectacle that inspired countless parodies (most notably by Joe Jonas), “Single Ladies” is simply the perfect dance video experience. It’s a silvery medley of thundering sass, like we’re watching 10,000 volts of electrical fire being pumped into the Supremes’ hips. Beyonce’s movements are intoxicating, and her gyrating backups match her step for step.

7. Lauryn Hill, “Doo Wop (That Thing)” (1999)

By the late ’90s we’d waited a long time for a breakthrough R&B video; we’d enjoyed scores of great rap videos (Missy Elliott’s “The Rain (Supa Dupa Fly)” and Puff Daddy’s “Mo Money, Mo Problems,” for starters) and a couple of danceable slow jam hits (Brandy and Monica’s “The Boy is Mine” comes to mind), but Lauryn Hill’s “Doo Wop (That Thing)” was a glorious video boasting classic soul, new wisdom, and the superfly side-by-side visual of Lauryn Hill’s ’60s-styled and modern-day performances. Her crackling, cocoa-y  voice and block party charisma make this an ageless gem.

6. REM, “Losing My Religion” (1991)

It was always so awesome when Michael Stipe embraced his melodramatic flair in music videos. He notoriously hated lip-syncing, but he gave it a shot with this perfect, sublimely disturbing video chockablock with religious detail and spooky lighting tricks. Too bad he stole most of his weird dance moves from the #5 artist on this list…

5. Sinead O’Connor, “Nothing Compares 2 U” (1990)

She may have inspired Michael Stipe’s trippy choreography in her “Emperor’s New Clothes” clip, but it’s “Nothing Compares 2 U” that holds up as one of the most striking clips in video history. Its visual spareness is so effective because it puts that much more emphasis on O’Connor’s unbelievable vocal performance, and the single tear that trails down her cheek is worthy of lachrymose applause from Godley & Creme, litter-conscious Native Americans, and Glenn Close at the end of Dangerous Liaisons.

4. Jamiroquai, “Virtual Insanity” (1997)

Like OK Go’s “Here It Goes Again” a decade later, Jamiroquai’s “Virtual Insanity” trapped us in a small space with commonplace furniture and made for a startling video moment that seems to defy time and space. Lead singer Jay Kay boogies around the shifting floor plan, and though it seems like the floor is moving, director Jonathan Glazer ingeniously filmed “Virtual Insanity” by making the walls move. It’s mind-blogging, and the bloodshed at video’s end is from our brains exploding.

3. Madonna, “Ray of Light” (1998)

The reigning czarina of music videos took to the streets for her only Video of the Year winner. Her jolty dance moves juxtaposed with the blitzkrieg of cityscape visuals is a one-of-a-kind masterpiece, a stunning way of communicating the seismic nature of the world’s daily grind. It’s impossible to think of “Ray of Light” without remembering the video; they don’t seem to exist without each other. My favorite part? The end sequence, where a tanktopped Madonna gets down on a fabulous dance floor.

2. Pearl Jam, “Jeremy” (1993)

This might be the only dead serious video I’ve ever been completely on board with. “Jeremy” is a harrowing clip about a disturbed grade-schooler whose rage becomes the stuff of national headlines. A chilling example of MTV high art, and I’m still amazed by the power of Eddie Vedder’s onscreen presence as the story’s “narrator.” An unforgettable reality check that never feels pretentious or unwilling to address true devastation.

1. Peter Gabriel, “Sledgehammer” (1987)

It still may be the most played clip in the history of the channel (Peter Gabriel once wrote to MTV asking them to stop playing “Sledgehammer” already), and that’s for good reason: You can always spot something new and cool in “Sledgehammer,” the groundbreaking claymation video featuring Peter Gabriel’s head, train tracks, more clay, and creepy blinking. It’s a creepy, wholly delightful, exceptional video. It will likely never be supplanted on this list.


The worst “Video of the Year”?: Christina Aguilera, Lil Kim, Mya, and Pink’s “Lady Marmalade” (2001). Shudder.

The weirdest distinction: Rihanna and Eminem have won Video of the Year twice, but Michael and Janet Jackson never won. 

Almost made the list?: 11. Lady Gaga’s “Bad Romance,” 12. Missy Elliott’s “Work It,” 13. The Cars’ “You Might Think,” 14. Rihanna’s “We Found Love,” 15. Aerosmith’s “Cryin'”