12 Weirdest Grammy Moments of All Time

April 2024 · 6 minute read

The Grammys have been host to a number of odd awards show moments. To prepare for whatever could possibly happen this year, we looked back at 12 of the weirdest speeches, mishaps, and more from Grammys past.

Stevie Wonder and Bob Dylan Present (1984)

Stevie Wonder and Bob Dylan have a chemistry that’s as strange as it is charming. Wonder hams it up the entire time he’s up at the podium — at one point ripping up a sheet of paper and trying to get the audience to vote then and there on the award via applause — while Dylan stands nearby almost nervously, only occasionally leaning in to say something. And yes, Dylan wears his sunglasses inside.

Jethro Tull: Best Hard Rock/Metal Band (1989)

https://youtu.be/sibnfB2i8Z4

Fans were excited when the Recording Academy announced a new category for hard rock and metal performances, but that excitement dwindled quickly when in its first year, Jethro Tull managed to beat out Metallica (the favorite for the win), AC/DC, Iggy Pop, and Jane’s Addiction in what is still considered one of the oddest Grammy wins of all time.

Milli Vanilli’s Best New Artist Trophy Taken Back (1990)

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In 1990, it was announced that Milli Vanilli’s Grammy trophy from 1989 for best new artist would be taken back after it was revealed that Robert Pilatus and Fabrice Morvan didn’t sing on their album “Girl You Know It’s True.” This was the first time the Recording Academy would make this move.

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Eddie Vedder Doesn’t Care About His Grammy Win (1996)

https://youtu.be/U16Q77Va4sc

When Pearl Jam won its first Grammy, for best hard rock performance, Eddie Vedder casually walked onstage and proceeded to tell the audience just how pointless he thought the honor was. “I don’t know what this means. I don’t think it means anything. That’s just how I feel.” He then capped off his perplexing speech with, “thanks, I guess.”

Ol’ Dirty Bastard Jumps Onstage (1998)

https://youtu.be/ENQ9qbUVdg4

Long before Kanye hopped onstage to interrupt Taylor Swift, ODB was doing it to Puff Daddy. After losing best rap album, the musician got on stage to let everyone know that Wu Tang was “for the children” and to complain about how much he spent on his suit in anticipation of winning the award.

The Soy Bomb (1998)

https://youtu.be/w0k7rKsCiLg

In what might be the most ridiculous moment in Grammy history, performance artist Michael Portnoy crashed a Bob Dylan performance of “Love Sick” shirtless and with “Soy Bomb” written on his chest, and proceeded to dance front-and-center until he was hauled offstage.

The Dress (2000)

https://youtu.be/6faZ5y4YhEw

Few fashion choices have sent as many ripples through pop culture as the green Versace dress Jennifer Lopez wore to the 2000 Grammys. Nearly everyone had an opinion on the revealing outfit following the show. It even led to imitations — most famously, “South Park” creators Matt Stone and Trey Parker wearing versions to the Oscars the following month.

Lady Gaga Hits the Red Carpet in an Egg (2011)

Lady Gaga is the queen of making a statement on the red carpet, but arriving inside an egg carried by shirtless men is some next level stuff. Adding to the weirdness, the performer has said she spent three days in the egg before coming out for her performance of “Born This Way” at the show.

CeeLo Green Performs ‘F— You’ with The Muppets and Gwyneth Paltrow (2011)

If you gave someone an infinite amount of guesses — with hints — to name two people to perform “F— You” with CeeLo Green at the Grammys, it would be safe to assume nobody would correctly choose the Muppets and Gwyneth Paltrow.

Johnny Depp’s Hollywood Vampires Perform Lemmy’s Tribute (2016)

https://youtu.be/BpR6tROunsE

The death of rock icon Lemmy sent a shockwave through the music world in 2015, and a Grammy tribute to the Motorhead legend was inevitable. It was a true head-scratcher when it was announced that Johnny Depp’s band Hollywood Vampires would be the group performing the tribute.

Twenty One Pilots’ Underwear Speech (2017)

When Josh Dun and Tyler Joseph dropped their pants before heading onstage to accept best pop duo at last year’s show, fans were on the edge of their seats as to what would happen next. What followed was a heartfelt speech about how they used to watch the Grammys in their underwear back in Ohio and a promise that if they ever won, they’d accept the award in them, too.

Adele Wins, Thinks Beyonce Should Have (2017)

Adele wrapped up a night of tons of Grammy wins (album of the year, record of the year, song of the year, etc.) in 2017 by doing the only logical thing: admitting Beyonce probably should have won instead. “All us artists here, we f—ing adore you. You are our light.”

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