The 15 Most WTF Moments In VMA History

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Each and every year since the program debuted in 1984, audiences have been tuning into the Video Music Awards en masse for a chance to see two things: That year's hottest musical acts perform live AND what happens when you put said hottest musical acts together in a relatively confined space. Thankfully for viewers, the combination of the intense media spotlight, oversized egos, and chemical stimulants have resulted in some truly memorable jaw-dropping moments over the show's 29 year history, moments that we have collected together into the following list: The 15 Most WTF Moments In VMA History.

15. Lil Mama Finds Herself In An "Empire State Of Mind" (2009)

When it comes to generational-defining anthems, you'd be hard pressed to find many (any?) songs that do it better than "Empire State Of Mind." So, naturally, it made perfect sense for MTV to book the song's creators, Jay Z and Alicia Keys, to perform the monster hit as the closing song at the 2009 VMAs. As the performance drew to a conclusion, though, Brooklyn-bred rapper Lil Mama somehow made her way on stage, where she posed alongside Hov and Alicia as the song's final notes played. That wouldn't have been such a big deal had Lil Mama actually, you know, had anything to do with the song, but she, in fact, did not. Now you know why Jay looks so perturbed in that photo above!

14) It's A Bird, It's A Plane, It's ... A Full Moon? (1992)

Howard Stern hadn't yet become the King Of All Media when he was asked to appear at the 1992 Video Music Awards and, in many ways, this was his first introduction to a widespread national audience. So what did he do to make an impression? He arrived to the show with the busty temptress Jessica Hahn (look her up) on his arm and dressed as Fartman, a faux-superhero character that was a recurring part of his radio show. He made his VMA debut by being lowered onto the stage from the rafters wearing a pair of assless tights, a memory that we unfortunately have been able to shake out of our brains despite desperately trying to do so for over 20 years.

13) Say Hello To Nathaniel Hornblower (1994)

Back when Kanye West was in high school and Taylor Swift was in pre-school, a rogue citizen of Switzerland named Nathaniel Hornblower stormed the stage of the VMAs to interrupt the acceptance speech that R.E.M. was about to give for an award given to "Everybody Hurts." Hornblower, later revealed to be Adam "MCA" Yauch of the Beastie Boys, commanded the stage for a glorious 28 seconds before MTV security hauled him off-stage, heaping praise on "Sabotage" director Spike Jonze and taking credit for "all the ideas in Star Wars."

12) Eminem Loses His Cool When A Puppet Tries To Interview Him (2002)

Based on his pop culture skewering videos like "My Name Is" and "The Real Slim Shady," one would've guessed that Eminem had a sense of humor. Well, one would be wrong. Triumph The Insult Comic Dog (aka Robert Smigel) attempted to interview an unwilling Em at the 2002 VMAs, and almost found himself on the receiving end of a series of blows from Marshall Mathers and his (late) D12 pal, Proof. Triumph aired his response to the matter on Late Night With Conan O'Brien a few days later, which you can watch below.

11) "The World Is Bullsh*t" (1997)

Have you ever been at a wedding where one of the (possibly inebriated) groomsmen or bridesmaids jumps on the mic and makes a really awkward, rambling speech that everyone in the room wishes would somehow, mercifully, magically end without causing them any further embarrassment? Well, that's sort of what happened to Fiona Apple at the 1997 VMAs, only swap "wedding speech" for "Best New Artist acceptance speech." Just like our analogy, you know you're in for a trainwreck when a speech begins with "Oh man, I didn't prepare a speech." If Fiona were granted the power to call a "do over," you can bet this quirky yet fiercely intelligent artist would use it for this moment.

10) Michael Jackson Awkwardly Frenches Lisa Marie Presley (1994)

Most couples are not fortunate enough to have their first kiss caught on tape. While we can't be certain whether or not the wedding between the King of Pop and Elvis' daughter was "real," we do know that this kiss between the two certainly felt like the couple was breaking new ground. "And they said it wouldn't last!" (Spoiler Alert: It didn't.)

9) Kid Rock Fights Tommy Lee (2007)

We will never know exactly what words were traded between Pamela Anderson's exes Kid Rock and Tommy Lee that caused them to come to blows during the 2007 VMAs in Vegas, but we CAN venture a guess: "You gave me Hep-C!" "No, YOU gave me Hep-C!" (Cue fisticuffs.)

8) Courtney Love Throws Her Shoe At Madonna (1995)

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Courtney Love was at her height of narcotized messiness when she drunkenly stumbled onto the set of the 1995 Video Music Awards aftershow, hosted by the unflappably cool Kurt Loder. Give major bonus points to Madge for being the "bigger" person here and not going gorilla on a clearly intoxicated Courtney, but we're quick to admit that we miss the days when music stars weren't so well-trained by their PR folks and were still willing to make total fools of themselves on camera. #TEAMCOURTNEYLOVE

7) "Ain't Nobody's Business But Mine And My Baby's" (2012)

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Until Tom Arnold and Roseanne Barr get back together, it's safe to say that Rihanna and Chris Brown will remain America's LEAST favorite couple (even though they are no longer together). These two briefly reconciled for what they thought was an off-camera kiss at the 2012 VMAs, which led to a tempestuous reconciliation later. America asked "Why?", and Chris and RiRi responded with the track "Nobody's Business" that appeared on Rihanna's 2012 album, Unapologetic.

6) Diana Ross Cops A Feel Of Lil Kim's Boob (1999)

What is it with female hip hop artists with the name Lil and VMA controversy? We already discussed what went down with Lil Mama, but that pales in comparison to what happened to Lil Kim back in 1999. The pint-sized rapper showed up to the VMAs with her left tidday totally exposed, save for some purple rhinestone pasty thingie. Well, when Queen Diana Ross showed up on stage to present an award alongside the Brooklyn babe, she couldn't help but do what everyone in the audience was secretly thinking about: Playing with that exposed breast!

5) There's Nothing Virginal About Madonna (1984)

The very first Video Music Awards were held in 1984 and hosted by Dan Aykroyd and Bette Midler. Jazz legend Herbie Hancock stole the evening by winning Video Of The Year for his (then) futuristic "Rockit," but all anyone remembers nearly 30 years later is Madonna's stunning performance of "Like A Virgin." Dressed up in a white wedding dress (complete with some provocative garter action), Madge writhed around the stage of Radio City Music Hall, causing parents around the nation to cover up the eyes of their children. The performance seems almost quaint all these years later, but at the time, this got many of America's foremost conservative cultural critics' panties in a proverbial bunch.

4) Britney's Zombie-Like Performance Of "Gimme More" (2007)

That extra large picture pretty much says it all. Years before The Walking Dead became the most popular show on television, a drugged-up and out-of-shape Britney Spears turned in a zombified performance of her "comeback" single "Gimme More" at the 2007 VMAs. Her extensions were wack, someone convinced her to wear a too small outfit, she was unsteady on her feet, and it appeared as if she had only learned the dance routine—not to mention the lyrics— for the song minutes before going on stage. This is one of the saddest moments in VMA history, one that still makes us say "WTF?" all these years later.

3) The Kiss (2003)

What can be said about the kiss between Madonna and Britney at the 2003 Video Music Awards that hasn't already been said? Sadly, the world pretty much ignored poor X-Tina's role in this all-time memorable VMA moment (not to mention Missy Elliott's follow-up cameo), but to this day, our favorite thing about this epic smoochfest remains Justin Timberlake's hilariously angry response. (Well, that and Queer Eye star Carson Kressley's exuberant response behind the Trousersnake!)

2) IMMA LET YOU FINISH, BUT... (2009)

If we've told you once, we've told you a thousand times. When you drink an entire bottle of cognac on the red carpet, BAD THINGS ARE GOING TO HAPPEN. Kanye West will attest to this, as will Taylor Swift! As big as the music careers of these two superstars are (and will be over the next 30 years), THIS will be the moment that forever defines the two of them.

1) Too Hot To Handle (1989)

The 1989 Video Music Awards have largely been forgotten, thanks largely to the still-impossible-to-believe upset that Neil Young's "This Note's For You" pulled over Madonna's "Like A Prayer" in the Video of the Year category. However, a promising R&B talent named Bobby Brown performed a song from the Ghostbusters 2 soundtrack, "On Our Own," and made VMA history along the way. Now, we'll say this: We don't know for sure if the vial that Bobby Brown dropped on the stage floor during his performance and then quickly snatched up contained cocaine, but we also don't know that it DIDN'T contain cocaine. For the record, in the fantastic book I Want My MTV, Bobby Brown claims "That was my diamond bracelet falling off my wrist," but you can draw your own conclusions after watching Brown's, um, highly energetic and off-the-charts sweaty performance!