Video Music Awards All-Stars: The 10 Biggest-Winning Music Videos (Did They Deserve It?)


Nearly every truly iconic music video since 1984 has been nominated for at least one Video Music Award in its year of eligibility, but in the twenty-seven years that the ceremony has been held, only ten individual music videos have won five or more Moonmen. (This year, Adele‘s “Rolling In The Deep” and Katy Perry‘s “E.T.,” featuring Kanye West, could potentially join the club.) These videos got the attention and praise of everybody in their respective years of release. But do they stand the test of time? What about their competition? Here’s our look at the ten most-lauded videos in VMA history.

Madonna, “Ray of Light”: Five VMAs (of eight nominations)
Concept: Madonna raves on fast-forward all over the planet.
Competition: “Ray Of Light” wasn’t the only video with eight nominations: Garbage‘s video for “Push It” had as many nods (though, ultimately, no wins). We’d totally forgotten about “Push It,” actually, and its stocking-masked nun heist/exorcism would be huge today, because it looks like a Lady Gaga video from the 1990s, and if there are two things music fans like these days, they’re Lady Gaga and the 1990s. The year of eligibility for this ceremony was also the height of jiggy rap, but while Diddy‘s five nominations were split among four videos (Puff Daddy and the Family: “It’s All About The Benjamins”; Notorious B.I.G. Featuring Puff Daddy: “Mo Money Mo Problems”; Mariah Carey Featuring Puff Daddy and the Family: “Honey (Remix)”; Puff Daddy & Jimmy Page: “Come With Me”), Will Smith got as many nominations just for “Gettin’ Jiggy Wit It” (though the video only won one Moonman).
Verdict: While we love “Push It,” the fact that we had to refresh our memory sort of proves that “Ray Of Light” was simply the stronger video that year. As for jiggy rap? Hype Williams was robbed, sure—none of the Best Direction nominees, even, were jiggy rap—but Diddy has gotten his fair share of VMAs over the years (and even hosted one of the ceremonies). HOLDS UP

INXS, “Need You Tonight”/”Mediate”: Five VMAs (of eight nominations)
Concept: A cut-and-past aesthetic with multiple exposures, mostly in black and white (important exception: heartthrob lead singer Michael Hutchence in full color). Then a riff on “Subterranean Homesick Blues” and (what else) a sax solo!
Competition: George Harrison‘s “When We Was Fab” had six nominations but no wins. U2 had four nominations each for “I Still Haven’t Found What I’m Looking For” and “Where The Streets Have No Name”—but the two videos competed against each other in three categories, which probably split the 1988 vote (and U2 walked away empty-handed). Astonishingly, Michael Jackson‘s “Bad” and “The Way You Make Me Feel” only had one nomination apiece (both for Best Choreography; they lost to Janet Jackson‘s “The Pleasure Principle”). One of MTV’s most requested videos that year, “Welcome to the Jungle,” won in its only category. George Michael‘s “Father Figure” was nominated once (and “Faith” not at all). And those are just the biggest of the big.
Verdict: We can’t argue with the “Need You Tonight”/”Mediate” single, but the video is very much of its time, and there was such a wealth of top-level contemporaneous videos that were not getting recognized. Even among the videos that got nominations, “Where The Streets Have No Name” (an iconic rooftop video) got nominated again, in 2009, for Best Video (That Should Have Won a Moonman). DOES NOT HOLD UP

Herbie Hancock, “Rockit”: Five VMAs (of eight nominations)
Concept: Piecework robots, hydraulics, puppets, lights, record-scratch video edits, and Hancock on the television screen. A surreal nightmare, or maybe just a post-human dance party.
Competition: “Thriller.” Believe it or not, the Michael Jackson video was only nominated for six VMAs (and only won three). Also in 1984: “Every Breath You Take,” giving The Police eight nominations but only one Moonman.
Verdict: “Rockit” is one of the best videos of all time, and any other year we wouldn’t question its wins. But as a Dave Chappelle character once said, “‘Thriller’, man. ‘Thriller.’SPLIT DECISION

Green Day, “Boulevard of Broken Dreams”: Six VMAs (of six nominations)
Concept: Green Day walks the empty street on the Boulevard of Broken Dreams. There are some damaged-footage effects.
Competition: The only other video that even got five nominations was U2‘s “Vertigo,” but there were plenty of strong videos that year, like Mariah Carey‘s “We Belong Together,” Missy Elliott‘s “Lose Control,” Amerie‘s “1 Thing,” and especially R. Kelly‘s “Trapped In The Closet.”
Verdict: Maybe we’re just being contrarian, but “Boulevard Of Broken Dreams” doesn’t give us anything visually that we can’t just hear in the song, and if we wanted to see Green Day walk through their video we’d watch “When I Come Around.” DOES NOT HOLD UP

The Smashing Pumpkins, “Tonight, Tonight”: Six VMAs (of eight nominations)
Concept: Jonathan Dayton and Valerie Faris send the Smashing Pumpkins on Georges Méliès‘s voyage to the moon.
Competition: The heavy hitters: Alanis Morissette, “Ironic” (three wins of six nominations); Bjöork, “It’s Oh So Quiet” (one win of six nominations); Bone Thugs-N-Harmony, “The Crossroads” (no wins of five nominations); Foo Fighters, “Big Me” (one win of five nominations). Other notable exclusions: 2Pac (featuring Dr. Dre and Roger Troutman) “California Love” and Busta Rhymes‘s “Woo Hah!! Got You All in Check,” each with one nomination and no wins.
Verdict: As much as we love the Busta video, the bigger crime is that Missy Elliott‘s “Supa Dupa Fly” didn’t win any of the three Moonmen it was nominated for a year later. As for 1996? “Tonight, Tonight” is as strong a candidate as any (though “Tha Crossroads” ought to have gotten some recognition), and its 1902 referent makes it less bound to time and place in the way that, say, “Ironic” is. HOLDS UP

a-ha, “Take on Me”: Six VMAs (of eight nominations)
Concept: Our comic-book racing hero breaks down the fourth wall to reach his real-world love.
Competition: Dire Straits‘ computer-animated satire “Money For Nothing,” with eleven nominations and two wins; Robert Palmer‘s “Addicted to Love,” with five nominations and one win.
Verdict: We were sure this would be the one that was least deserving of its VMA sweep, but now we’re thinking 1985-1986 just really sucked for music videos. “Money For Nothing” might be as memorable, and “Addicted to Love” more iconic, but especially considering “Take On Me” won Viewer’s Choice, we can’t think of a video that really should have won bigger that year. HOLDS UP

Fatboy Slim, “Weapon of Choice”: Six VMAs (of nine nominations)
Concept: Christopher Walken defies gravity and expectations with inventive choreography.
Competition: *NSYNC, “Pop” (four wins of six nominations); Christina Aguilera, Lil’ Kim, Mya, and Pink, “Lady Marmalade” (two wins of six nominations); Missy Elliott, “Get Your Freak On” (no wins of six nominations); Eminem Featuring Dido, “Stan” (no wins of five nominations)
Verdict: We’re not sure what’s more astonishing—that in 2001 MTV had separate Moonmen for Best Rap Video and Best Hip-Hop Video, or that even under those circumstances Missy still got shut out. “Weapon Of Choice” is a singular video, though. HOLDS UP

R.E.M. “Losing My Religion”: Six VMAs (of ten nominations)
Concept: A high-concept, oil-painting clip that, frankly, doesn’t get enough credit for introducing certain types of iconography to music video (technical camera and light adjustments as effects; evocations, rather than full-on portrayals, of imagery, like the angel wings).
Competition: Chris Isaak‘s “Wicked Game” (seven nominations, three wins); C+C Music Factory “Gonna Make You Sweat (Everybody Dance Now)” (seven nominations, two wins); George Michael‘s “Freedom ’90” (five nominations, no wins).
Verdict: Another not-so-strong year for music videos. Even still, “Freedom ’90” is an all-time favorite and it feels slightly anti-populist to stick with R.E.M. (though much less so than with “Rockit” and “Thriller”). SPLIT DECISION

Lady Gaga, “Bad Romance”: Seven VMAs (of ten nominations)
Concept: High-fashion meets high-class hooker at the Bath Haus of Gaga.
Competition: Eminem‘s “Not Afraid” was eight times nominated (and won twice, in categories for which “Bad Romance” was nominated) but the only thing really on the level of “Bad Romance” last year was Gaga’s other nominated video (with Beyoncé), “Telephone.”
Verdict: It’s tough to say whether a video “holds up” less than a year later, but Gaga’s Fame Monster period is the peak of her visual creativity, and though we like “Telephone” somewhat more, the synthesis in “Bad Romance” of all-white-everything European goth-chic with the aesthetic of classic choreographed dance videos is striking in a unique way. HOLDS UP

Peter Gabriel, “Sledgehammer”: Nine VMAs (of ten nominations)
Concept: The building blocks of life become Peter Gabriel’s face, which then becomes fruit, modern art, and clay, and then Gabriel walks off into the stars. Basically it’s the catchiest animation clip reel ever (with claymation contributions from future Wallace & Gromit creator Nick Park!).
Competition: Janet Jackson‘s singles from Control, Paul Simon‘s “You Can Call Me Al,” the Genesis video for “Land Of Confusion,” Jermaine Stewart‘s “We Don’t Have To Take Our Clothes Off,” Run-DMC‘s “Walk This Way,” and maybe a handful of others.
Verdict: Even considering the bias MTV may have had against pop or rap videos winning big at the VMAs, it’s practically impossible for a video to win that big without being head and shoulders above the rest. HOLDS UP

There you have it: the big winners mostly deserved to win. That’s comforting, right? As for Adele and Katy Perry, we’ll see on Sunday at 9PM if they’ll be joining the club. Got a particular video in mind that could give one of these clips a run for their money in their respective eligibility years? Let us know in the comments.

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