Top Five Most Shocking Grammy Moments of All Time

Bob Dylan and Michael "Soy Bomb" Portnoy
Bob Dylan and Michael "Soy Bomb" Portnoy

This weekend is the 55th Annual Grammy Awards. Viewed by many as music's biggest night, the telecast has been home to lifelong icons finally getting their due, musical phenomenons explode and some of the most shocking moments in broadcast television history. As great as the former are, it's the unpredictable moments that occur magically during one of entertainment's most rehearsed nights that keeps us coming back year after year. But while the elegant performance and underdog victories are always fun surprises, a few particular moments have been burned into the pop-culture spectrum as among the most startling of all time. Here's our picks for top five most shocking Grammy moments of all time.

5) 2pac Reunites KISS1996

Given the off/on reputation of the Grammys as being straight-laced and safe to a fault, certain artists would typically never been seen on their stages. It wasn't until 1990 that a rap Grammy was awarded on television, with Young MC taking home only the second trophy yet given to the genre. That's why 2Pac at the height of gangsta rap's controversy would be memorable enough. BUT THEN, he brings out the reunited fully made-up shock rock pioneers KISS. It's crazy to think 17 years later what an incredible cross-section this was for pop culture, not to mention how cool it is to see the artists likely responsible for roughly 40% of all Spencer's Gifts revenue on the stage at once.

4) Bob Dylan vs Soy Bomb1998

As funny as Tim Heidecker's

fake Bob Dylan Super Bowl Halftime Show announcement

and song leak earlier this year was, had it been true it wouldn't be the most bizarre of Bob Dylan's media appearances. On the night of the 1998 Grammy Awards, during Dylan's performance, a hired back-up dancer-turned-performance artist named Michael "Soy Bomb" Portnoy began spastically dancing. Dylan remained unfazed, only adding to the sheer spectacle of the moment. We don't blame CBS for not paying Portnoy his agreed $200 background fee. He's got a lot of nerve.


3) Billy Joel's River of Delays1994

A particularly fierce topic of Grammy debate is which moment of the 1994 telecast was the most controversial. All possible contenders revolve around that year's lifetime achievement award, which was awarded to Frank Sinatra. From U2 hooligan Bono dropping a live "F-bomb" to Sinatra's stumbling acceptance speech being abruptly cutoff as the show went to commercial, a lot didn't go right that night. But our pick has to be Billy Joel stopping the show and mocking the wasting of valuable commercial time during "River of Dreams." With Sinatra himself was thankful the show cut his speech, Joel took offense and struck back the best way he knew how.

2) John Lennon and Paul Simon Innovate Awkward Passive Aggression 1975

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How's this for a wacky idea that's sure to create a moment that will last forever? Take one-half of two celebrated and recently separated critically acclaimed and wildly successful songwriting teams, and have them present an award together?! There's something just not right about John Lennon and Paul Simon being prompted to read banter, but things only got weirder as Simon's former partner Art Garfunkel took the stage to accept the coveted Record of the Year award on Olivia Newton-John's behalf. When the playful digs outweigh the magnitude of a tuxedo shirt, you know you have a classic(ly bizarre) moment.


1 ) Ol' Dirty Bum-Rush 1998

But nothing compares to the late great Ol' Dirty Bastard bum-rushing the Grammys stage. The same year as the aforementioned "Soy Bomb," 1998 saw Shawn Colvin's acceptance speech for "Sunny Came Home" interrupted by the one-time Big Baby Jesus showing off his duds and immortally declaring "Wu-Tang is for the Children!" Before his untimely death in 2004, Ol' Dirty Bastard had countless explosive unpredictable public moments to his name. But for the most unhinged member of the Wu-Tang Clan, his highest profile interjection was on that Grammy stage.

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