The 30 Weirdest Grammys Moments of All Time

Singer Lady Gaga performs onstage during The 53rd Annual GRAMMY Awards held at Staples Center on February 13, 2011 in Los Angeles, California. (Photo by Jeff Kravitz/FilmMagic)

There’s a good reason why the Grammy Awards coined the term “Grammy Moments” to describe the one-of-a-kind collaborations and elaborate performances that take place during each year’s broadcast. There’s always at least one off-the-wall, meme-able event that becomes part of awards-show lore. Last year, it was John Travolta’s teleprompter problems and Twenty One Pilots’ boxer shorts; previous years have given us impractical costumes, head-scratching indie rock wins, and Kanye West trying to jump on stage.

Expect something similarly outlandish to occur during the 2018 Grammys, taking place at Madison Square Garden from 7:30 p.m. EST on Sunday, January 28. Until then, tide yourself over with the 30 weirdest Grammy moments of all time.

30. “Who Let the Dogs Out?” wins the Best Dance Recording Grammy (2001)

From a statistical standpoint, “Who Let the Dogs Out?” winning the Grammy for Best Dance Recording in 2001 was an outlier. Baha Men’s barking earworm was the only nominated tune not to grace the Billboard dance charts. (In fact, Enrique Iglesias’ “Be With You” actually hit No. 1.) Aside from that, it beat out Europop phenom Eiffel 65, then-pop superstar Jennifer Lopez, and perennial electronic darling Moby to win the award. The power of the Rugrats in Paris soundtrack (which helped the song become a hit) is strong with this one. —Annie Zaleski

29. Twenty One Pilots delivering a surprisingly sentimental speech in their underwear (2017)

Before they even walked up to accept their Grammy for Best Pop Duo in 2017, Twenty One Pilots stripped down to their boxers, apparently paying tribute to the days when the duo would sit at home and watch the award show in their underwear. In an even more unexpected twist, their speech ended up being surprisingly heartfelt, which just goes to show that good public speaking skills go a long way. —Sam Goldner

28. Gorillaz and Madonna join forces for a lethargic collaboration (2006)

https://www.youtube.com/watch?v=Bux38qQXlb4

Despite being a cartoon band, Gorillaz have always done an admirable job translating their electro/hip-hop hybrids to a live setting. This 2006 Grammys performance of “Feel Good Inc.” is a notable exception. The animated members seem bored: 2-D, voiced by Blur‘s Damon Albarn, checks his virtual phone during the song, and drummer Russel Hobbs nods off. Even an energetic Madonna showing up to interact with Gorillaz and sing her then-hit “Hung Up” can’t save the lethargic performance. The only redeeming factor is the non-virtual De La Soul coming onstage to reprise their buoyant “Feel Good Inc.” bridge—and Madonna ditching Gorillaz to finish her own song. —AZ

27. Steely Dan winning Album of the Year… in 2001 (2001)

The Grammys have always favored old, safe bets over newer, riskier voices, but this one was just ridiculous. In the same year that Radiohead released Kid A, Eminem released The Marshall Mathers LP, and Beck released Midnite Vultures, the Grammys chose to give Album of the Year to soft-rock vets Steely Dan for Two Against Nature. And this was before it was even cool to like Steely Dan again. —SG

26. John Travolta awkwardly introduces Keith Urban and Carrie Underwood (2017)

To be fair, actor John Travolta was clearly nervous to be introducing Keith Urban and Carrie Underwood, kicking off his speech with the embarrassing intro, “I know what you’re all thinking—you’re thinking, ‘Damn, where he get all that bling from?” (Er, not really.) After noting that he couldn’t read the teleprompter, ostensibly because of poor eyesight, Travolta delivered the rest of the speech from cards, and welcomed Urban and Underwood by saying they’re “the most dynamic duo since Danny and Sandy.” (Grease reference, groan.) At least it wasn’t as awkward as him calling Idina Menzel “Adele Nazeem,” though, right? —AZ

25. Avril Lavigne mispronounces David Bowie’s name (2003)

This one surely ruffled the feathers of anybody out there who thinks that the kids today just don’t respect the greats. When reading the nominations for Best Rock Male Vocal Performance in 2003, Avril Lavigne butchered David Bowie’s name. Those whippersnappers…. —SG

24. Marvin Hamlisch wins the Best New Artist Grammy (1975)

The Best New Artist Grammy category is often eyebrow-raising—we’ll get to more examples later—but Marvin Hamlisch’s 1975 win felt particularly head-scratching. It wasn’t who the musician beat (Bad Company, David Essex, Graham Central Station, Johnny Bristol, and Phoebe Snow), but the fact that he had enjoyed success as a composer and writer for a full decade before nabbing the award. In fact, Hamlisch won three Academy Awards in 1974 for his work on soundtracks for The Way We Were and The Sting. AZ

23. Johnny Depp’s band is chosen as the tribute act for Lemmy (2016)

https://www.youtube.com/watch?v=BpR6tROunsE

Lemmy’s tragic passing in late 2015 sent a shockwave through the world of hard rock, so of course the Grammys chose to honor the Motörhead legend at the next year’s award show. Unfortunately, the most metal thing they could think of was to showcase Johnny Depp’s band Hollywood Vampires. Granted, the group also includes such luminaries as Alice Cooper and Joe Perry, but it’s hard to look past Jack Sparrow. —SG

22. Garth Brooks’ high-concept “Friends in Low Places” performance (1991)

https://www.youtube.com/watch?v=ueRxRcoVmjs

Garth Brooks is actually a decent actor, as proven by his Saturday Night Live hosting appearances and the whole Chris Gaines project. This high-concept 1991 performance of “Friends in Low Places,” however, didn’t quite hit the mark. Initially, the stage setting is a fancy dance full of people in formal gowns and tuxedos. Brooks shows up to the ball wearing his usual cowboy hat and striped shirt, acting like a drunk interloper who’s stumbled into the wrong party and keeps accosting the guests. After some personal reflection, the scene changes into a low-key and overly cheerful bar scene—that’s where he’s most comfortable, right?—that looks straight off the set of Beverly Hills, 90210. Ah, the ’90s. —AZ

21. Kanye West jumping on stage during Beck’s Album of the Year win… but then changing his mind (2015)

Talk about missed opportunities—when Beck snagged the 2015 Grammy for Album of the Year (when we all know it should’ve been Beyoncé), Kanye West leapt onstage seemingly to defend Queen B’s honor, only to back down seconds later. Perhaps it was just a joke, but sadly we’ll never know what the Kanye vs. Beck feud could have been. —SG

20. That time Foo Fighters performed during a dance music celebration (2012)

https://youtu.be/IVUNbKbf2cs

The Grammys love odd pairings, and it doesn’t get much weirder than this multi-artist performance from 2012, which featured EDM heavyweights (David Guetta, deadmau5), hip-hop stars (Chris Brown, Lil Wayne), and… rock ‘n’ roll lifers Foo Fighters performing their song “Rope.” Of course, the collaboration did have some precedent: The previous year, deadmau5 had released a rather ferocious remix of “Rope.” At the Grammys, Dave Grohl (who wore a pretty kickass Slayer tee for the occasion) and the rest of the band did a blazing rock version of the song, then segued into the remix with deadmau5 himself. —AZ

19. 50 Cent awkwardly walking across the stage after losing to Evanescence (2004)

https://www.youtube.com/watch?v=2jJ7bWO1Vcc

Apparently pissed that Evanescence beat him for the Best New Artist Grammy in 2004, 50 Cent jumped on stage shortly after Amy Lee was handed her award. It seems like he had second thoughts, though, as all he ended up doing was awkwardly walking across the stage behind the band before quietly returning to the audience. Half measure, much? —SG

18. Jack Black’s disembodied head introduces a misguided performance of OutKast’s “Hey Ya” (2004)

There are a lot of “WTF?” moments and bad decisions being made in this clip, but let’s start with Jack Black‘s disembodied head introducing OutKast, à la Jambi from Pee Wee’s Playhouse. Things get even more mind-boggling from there: André 3000 and a group of dancers dressed like Native Americans emerge from a teepee and proceed to dance throughout the “Hey Ya!” performance. Oh, and André 3000 is wearing silver space boots and bright green pants that look like they’re made of crepe paper. “Hey Ya!” is still an incredible song; this performance undermined that. In fact, the abundance of cultural appropriation, demeaning stereotypes and racism on display angered American Indian groups around the U.S., and CBS was forced to apologize. —AZ

17. Adele winning Album of the Year but saying Beyoncé should’ve won (2017)

Wrapping up a victorious night in which she clinched the Grammys for Album of the Year, Record of the Year, Song of the Year, and more, Adele spent most of her final speech saying that Beyoncé should’ve won instead. “All us artists here, we fucking adore you. You are our light,” she said emphatically through tears, proving once again that regardless of who wins, it’s all about Bey. —SG

16. When Milli Vanilli were stripped of their Best New Artist trophy (1990)

In November 1990, for the first time ever, the Grammys rescinded an award. Specifically, Milli Vanilli lost their 1989 Best New Artist Grammy, following revelations that performers Robert Pilatus and Fabrice Morvan did not actually sing on their blockbuster album Girl You Know It’s True. “I hope this action signals loudly and clearly to producers, record companies, and packagers that the Academy cares deeply about this issue,” Mike Greene, president of the Recording Academy, told The Los Angeles Times. “I hope this revocation will make the industry think long and hard before anyone ever tries to pull something like this again.” —AZ

15. Eddie Vedder saying the Grammys don’t mean anything (1996)

https://www.youtube.com/watch?v=U16Q77Va4sc

When Pearl Jam won the very first award at the 1996 Grammys, for Best Hard Rock Performance, Eddie Vedder walked onstage and proceed to muse ambivalently on the emptiness of the Grammys to a dead-silent audience: “I don’t know what this means. I don’t think it means anything. That’s just how I feel. There’s too many bands, and you’ve heard it all before. My dad would’ve liked it… my dad died before I got to know him… so that’s why I’m here. Thanks, I guess.” Way to open a show. -SG

14. Stevie Wonder and Bob Dylan presenting together (1984)

//www.dailymotion.com/embed/video/x55gzgc?autoPlay=0

The Grammys love odd couple presenters. In 1984, they paired Stevie Wonder and Bob Dylan, which made for one of the more hilarious (and charming) pairings of the time. Despite keeping his sunglasses on, Dylan is a little like a deer in headlights—perhaps because the jovial Wonder is having a grand old time, ripping up one of the cue cards and encouraging the audience to vote for the winner via applause. (A highly unorthodox move.) When the winner is finally announced (The Police‘s “Every Breath You Take”), Sting isn’t even there to accept, leaving both men at the podium trying to figure out what to do. —AZ

13. The O Brother, Where Art Thou? soundtrack winning Album of the Year (2002)

https://www.youtube.com/watch?v=yjHhs3_bzD8

O Brother, Where Art Thou? is a modern classic, in large part thanks to its beautiful soundtrack of traditional Appalachian folk songs produced by T Bone Burnett. But when you’re handing out the Album of the Year award to a movie soundtrack that largely consists of songs written 80-plus years ago, maybe you should just admit it was a slow year. —SG

12. CeeLo Green and Gwyneth Paltrow perform with Muppets (2011)

https://www.youtube.com/watch?v=ST7-t7g51XQ

CeeLo Green collaborating with Muppets for a sanitized version of “Fuck You” is kooky enough, especially because his flamboyant plumed outfit blends in with the colorful puppets. This 2011 performance gets even more head-scratching when Gwyneth Paltrow shows up to sing the hook. Paltrow had been nominated for a Grammy in 2009, but though she does have an excellent singing voice, it wasn’t quite right for the song. —AZ

11. Macklemore texting Kendrick Lamar to apologize for winning Best Rap Album (2014)

First off: Macklemore & Ryan Lewis beating out Kendrick Lamar’s good kid, M.A.A.D city, Drake‘s Nothing Was the Same, Jay-Z’s Magna Carta Holy Grail, and Kanye West’s Yeezus for Best Rap Album? Please. But Macklemore’s very-publicized “private” apology to Lamar for beating him was like pouring salt in the wound—even Lamar called the attention-seeking move “uncalled for.” —SG

10. Bon Iver wins the Best New Artist Grammy… in 2012

Think Bon Iver won the Best New Artist Grammy soon after the wide release of 2007’s For Emma, Forever Ago? Think again: Justin Vernon didn’t actually nab the trophy until 2012, the same year he also won the Grammy for Best Alternative Music Album for his second, self-titled effort. Vernon’s win fit within the timeframe parameters put forth by the Grammys’ governing body, but for indie music fans everywhere, it still felt very, very strange. —AZ

9. JLo wearing her now-classic green dress (2000)

https://www.youtube.com/watch?v=6faZ5y4YhEw

When JLo appeared on the Grammys red carpet wearing that eye-popping, flowing, green Versace dress, it sent a shockwave through the fashion world. Of all the crazy dresses and extravagant outfits people have worn to awards shows, few have caused as much of a ruckus as this one, even inspiring other celebrities to imitate it—as the South Park guys did at the Oscars just a month later. —SG

8. David Bowie not winning any Grammys for his art until after he died (2017)

https://www.youtube.com/watch?v=1Nm6Gues5ms

One of the most surprising things about Bowie is his lack of Grammy Awards. Save for a 2006 Grammy Lifetime Achievement Award, and a 1985 nod for Best Short-Form Video for Jazzin’ for Blue Jean, he never won any actual trophies for his art while alive. That all changed in 2017, when he won five awards: Best Rock Performance and Best Rock Song for “Blackstar,” and Best Alternative Music Album, Best Engineered Album, Non-Classical, and Best Recording Package, for his final record, Blackstar. —AZ

7. Ol’ Dirty Bastard jumping on stage to say Wu-Tang should’ve beat Puff Daddy (1998)

https://www.youtube.com/watch?v=ENQ9qbUVdg4

Apparently ODB was pretty upset about losing out Best Rap Album to Puff Daddy: A little bit later, as Shawn Colvin was walking up to accept her award for Song of the Year, he stormed onstage to deliver a tirade, claiming that “Wu-Tang is the best” and complaining about the expensive suit he bought for the show. Hope he kept the receipt. —SG

6. Frank Sinatra beating the Beatles for Album of the Year—two years in a row (1966, 1967)

Much like Bowie, the Beatles weren’t sure-fire Grammy locks. Case in point: Frank Sinatra beat out the Fab Four in the Album of the Year category in both 1966 (when Help! was nominated) and 1967 (the year Revolver got a nod). The Beatles did (rightfully) win the prestigious trophy for Sgt. Pepper’s Lonely Hearts Club Band in 1968, however. —AZ

5. Lady Gaga arriving to the Grammys in a giant egg (2011)

Leave it to Lady Gaga to take the red carpet game to the next level. She arrived to the 2011 Grammys carried in a giant egg by scantily clad assistants, eventually emerging for a knockout performance of “Born This Way.” She also claimed that she was in the egg for three days, which only adds to the levels of WTF here. —SG

4. The “Synthesizer Medley” featuring Stevie Wonder, Herbie Hancock, and more (1985)

https://www.youtube.com/watch?v=L4p7VIE9jQk

Let’s be clear: This bonkers synthesizer medley is awesome, and only goes off the rails near the end. A robotic voice commands each man onstage—legends Stevie Wonder and Herbie Hancock, and New Wave upstarts Thomas Dolby and Howard Jones—to identify themselves. Once locked in, each man (who’s encircled by a stacked fleet of synthesizers) plays snippets of hit songs and generally lets their keyboard-freak flag fly. Where things get weird is near the end: A spaceship-like light is lowered from the stage, which triggers a patriotic song medley as Dolby leaves the cozy synth circle to conduct the extravaganza like an eccentric orchestra maestro. Really, this is the kind of Grammys live performance by which all future live performances are measured. —AZ

3. Arcade Fire winning AOTY and no one knowing who they were (2011)

Even in 2011, Arcade Fire might have been the biggest indie act known to man, but their surprise Album of the Year win (for The Suburbs) still proved they were ultimately little fishes in a big pond. The wave of “who are Arcade Fire” tweets in the coming days only made their victory that much more gobsmacking. —SG

2. Metallica loses to Jethro Tull (1989)

//www.dailymotion.com/embed/video/xddi5m?autoPlay=0

In 1989, metal fans were heartened when the Grammy unveiled a new category, Best Hard Rock/Metal Performance Vocal or Instrumental. The optimism was short-lived: Metallica, who were favored to win for …And Justice For All, lost the category to Jethro Tull’s Crest of a Knave. (It’s worth noting Ian Anderson and co. also beat out Jane’s Addiction, Iggy Pop, and AC/DC.) It’s considered one of the most preposterous Grammys upsets ever, although at least Metallica had the chance to perform a menacing version of “One” on the telecast. —AZ

1. Michael Portnoy Soy Bombing Bob Dylan’s performance (1998)

https://www.youtube.com/watch?time_continue=31&v=w0k7rKsCiLg

Acclaimed performance artist Michael Portnoy was hired as a backup dancer for Bob Dylan at the 1998 Grammys, where he was supposed to groove in the background during a live version of “Love Sick.” But Portnoy had other plans: a few seconds into the song, he leapt to the front, ripping off his shirt to reveal the words “Soy Bomb” scrawled across his chest in ink. After flinging his arms around for an unreasonable amount of time (to the dismay of a visibly irritated Dylan), security finally ushered him offstage, dispelling the aura of chaos that briefly overtook the 1998 ceremony. —SG

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