What's ‪The Most WTF Moment in Grammy History‬?

Throughout its history, the Grammy Awards have witnessed moments that make you bless the invention of DVR or create a permanent handprint after one too many facepalms. Something about blending musicians of all ages, attempting to maintain industry integrity and win the night in ratings always makes for unpredictable results. (Live television!) With so many performances and strange bedfellows, the possibility for horrifying moments (or confounding award winners) abound, giving us much to unpack in the days that follow. There are of course more obvious choices like stage-crashing and intelligible rants, as well as moments that seem laughable or unjust in retrospect. We've done our work in selecting these memorable head-scratchers from years past, but it's up to you to decide which is the most definitively WTF. Vote in our poll! The winner will be revealed on Saturday, with some far less horrifying prize.


Let's make an analogy. Let's imagine the Grammys were picking Record of the Year solely based on hitting No. 1, and the crop of contenders included "Rolling in the Deep" (some things never change, even in hypotheticals), "Someone Like You" (see previous), "Born This Way," "Grenade" and "Party Rock Anthem." Now imagine if LMFAO won. Scandal! Outrage! But surely just a relic of hypotheticals and our modern, pop-sloppy times, no? Now imagine it's 1966, and your Best Rock & Roll Recording contenders include "Eleanor Rigby" and "Good Vibrations," as well as some track called "Winchester Cathedral" by some purposefully wacky group called The New Vaudeville Band that featured, in Cracked's words, "the kind of music your great-grandmother used to do the Charleston to with vocals sung through a megaphone to make them sound old-timey." There's just no way, right? Oh, there was a way. (But hey, Petula Clark's subsequent cover wasn't so bad, right? That sort of makes up for it, right, maybe a little, maybe the idea of it--nope, still WTF.)


This entry will get more and more WTF with time, not for the names involved (Thomas Dolby, Herbie Hancock, Howard Jones and freaking Stevie Wonder add up to more talent per square inch than entire swaths of Grammys past) but for almost everything else. There's the premise--a synthesizer medley? Why, that's called the radio these days! But back then, this was the future, in all its piano-mimicking, electronic glory, a path that could only lead to bigger science and bigger hair. There's that hair. There's the lack of even an attempt to hide that these flourishes were pre-recorded--one of the synthesizers isn't even plugged in. There's the mere phrase "synthesizer medley," did we mention that? There's the comedy of backstage shenanigans behind the scenes. But most of all, there's the fact that so much timeless talent could end up sounding so very of its time. With hair to match.


Horrifying in retrospect: Milli Vanilli won Best New Artist despite the world finding out their artistry consisted mainly of being frontpeople. Finding out a few years later. On the bright side, they did say the Grammy win went out to "all the artists in the world," even before they abdicated it.


Fluting rockers Jethro Tull are nobody's idea of metal, except for, oh, the entire Grammy voting establishment. Here's how it happened: Crest of a Knave, an album that qualifies as "metal" largely for not really sounding like Jethro Tull, was nominated alongside Metallica at their peak, as well as AC/DC, Iggy Pop and Jane's Addiction. Jethro Tull didn't even bother to show up; their nomination was that ludicrous.

You know where this is going: they won, presenters Alice Cooper and Lita Ford were captured in slow-motion emotional turmoil, from utter confusion to irritation to irritation disguised as amusement to the utter confusion to the urge to leave the stage, right now; Metallica wouldn't stop referencing it, and even Jethro Tull mocked themselves.


It's likely anyone would have been the teeniest bit rattled in the presence of the late Frank Sinatra, doubly so when given the task of delivering a televised speech on his behalf. Toothpick in mouth, Bono read what we're led to believe were previously recorded thoughts as an introduction to Sinatra's Lifetime Achievement Award. Starting off with a hearty "Right," he launched into a series of weird mob metaphors and references to the Catholic church—look to befuddled reaction shots from Sting and dumb grins from Tony Bennett to get the complete sense of WTF. Four rambling minutes later, Sinatra constructed a heartfelt thank you, as well as a dig about not being asked to come have a drink beforehand, too.


Before Kanye West let Taylor Swift finish, Wu Tang Clan's ODB had a public disagreement with the ruling in the Song of the Year category. As Shawn Colvin prepared to accept her award for "Sunny Came Home," ODB beat her to the mike—but not before giving presenter Erykah Badu a kiss on the cheek—to tell the crowd that he spent a nice chunk of change on his maroon suit in hopes of giving an acceptance speech. He then used his limited time to remind those at home that "Wu Tang is for the children," and to inspire a bigger budget for in-house security at all future award shows. This would never have happened to Paula Cole.


Just watch the thing. Then read performance artist Michael Portnoy's attempt to explain his performance-bombing: "Soy... represents dense nutritional life. Bomb is, obviously, an explosive destructive force. So, soy bomb is what I think art should be: dense, transformational, explosive life." He left a legacy, too; later on, Mumford and Sons would interrupt a Bob Dylan performance with soy-fed bombing. (Kidding. They did pretty well. But it's a miracle nobody made that joke at the time, right?)


In a year that Eminem managed to take hip-hop even further towards the mainstream and continue to push the FCC boundaries, veteran group Steely Dan saw their album Two Against Nature beat out The Marshall Mathers LP (as well as Beck's Midnite Vultures, Paul Simon's You're The One and Radiohead's Kid A). The win capped a night in which the duo took home four awards and publicly upset the year's most controversial and talked about performer—who still delivered the requisite water cooler moment with his performance alongside Elton John—as well as enraged the wrath of angry adolescent fans. If only social media had existed back then! No SD fan accounts would be safe from Eminem trolls.


The night's tribute to Sly and The Family Stone brought out Joss Stone, Steven Tyler, John Legend, Fantasia, Maroon 5, will.i.am, and eventually the man himself, in his first live performance since 1987. Stone emerged towards the tail end of the group number, taking charge on "I Want To Take You Higher" and allowing his blonde mohawk and silver metallic suit silence those "What has he been up to?" questions. There weren't many clues to pull from his performance, as he did his best not to acknowledge his fellow performers—or, as it turns out, the audience—but when you manage to trump the colorful bird's nest atop Tyler's head, you've truly opened yourself up to heaps of public commentary.

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