The VMAs’ Greatest Opening Moments: Pee-wee, ‘The Kiss,’ Jo Calderone And More!

From Madonna's kiss with Britney and Xtina to Gaga's antics, these are the VMA's best opening acts.

Everyone knows when step onto the VMA stage, you’ve got to seize the spotlight.
After all, this is your time to shine, your moment to make a memory. And that’s especially true if you’ve been tapped to open the show; not only will you set the tone for the entire evening, but there are two-plus hours of entertainment still to come, and, given the history of the Video Music Awards, well, you know anything can happen (and, more than likely will). So you’ve got to be great. In front of an audience filled with the most famous people on the planet, and millions of fans watching around the world. No pressure or anything.

It’s little wonder, then, that over the past three decades, the VMA’s opening slot has produced some of show’s most iconic moments: triumphant comebacks, touching tributes, thrilling performances … not to mention a few infamous missteps that have become the stuff of legend. Regardless, we’re still talking about them, and in the lead up to the 2013 MTV Video Music Awards, we’re taking a look back at the most memorable opening moments in VMA history.

In the early days (you know, the ’80s) the opening slot of the show was generally reserved for the hosts — who can forget Dan Akroyd and Bette Midler rising from the Radio City stage dressed as astronauts at the first-ever VMAs, or Eddie Murphy’s epic menagerie of sweaters in 1985? — while the real moments took place later (like, Madonna’s decade-defining “Like a Virgin” performance, which occurred some 40 minutes into the ’84 show … after Rod Stewart opened).

That all changed in 1991, when Paul Reubens, fresh off his headline-making arrest at an adult movie theater in Florida, made a surprise appearance at the opening of the show, and, decked out in his famous Pee-wee Herman suit, delivered a line for the ages: “Heard any good jokes lately?” The audience went wild, and a new standard was set.

Three years later, another star whose life had taken a tabloid turn attempted to silence his critics at the opening of the VMAs: Michael Jackson, whose marriage to Lisa Marie Presley had dominated gossip rags for much of the year, appeared on stage with his wife for a PDA session that did little to silence their naysayers, but did leave much of America squirming in their seats. “And just think, nobody thought this would last,” Michael proclaimed, seconds before devouring Presley’s face. Turns out, nobody was right (two years later, they were divorced) though Jackson did return to open 1995 VMAs, and delivered an epic medley of his hugest hits that, for a while at least, made everyone forget “the worst kiss ever.”

In 1997, the tone at the top of the show was decidedly different. Puff Daddy opened things with a touching tribute to his late friend, the Notorious B.I.G., performing “I’ll Be Missing You” along with Faith Evans, 112, Sting and a full gospel choir, while images of Biggie were broadcast on a screen behind him. Puff urged the audience to “put your lighters in the air for B.I.G.,” and they obliged, making for one of the most chill-inducing scenes in the show’s history.

Chris Rock hosted that year’s VMAs, and returned for his third stint as emcee in 2003 … just in time to have a front-row seat to an opening moment that’s since become one of the most-discussed of all time: the three-way lip-lock/passing-of-the-torch between Madonna, Britney Spears and Christina Aguilera, which has come to be referred to as “The Kiss.”

It started innocently enough, with Spears and Aguilera re-creating the iconic “Virgin” performance, right down to the tattered wedding dresses and floor routines, then, in a moment of gender-flipping brilliance, Madonna herself appeared dressed as a groom, and launched into her single “Hollywood.” Things quickly heated up, as the brides stripped down, danced with their soon-to-be “husband,” and then, much to the delight of hormones everywhere, the trio exchanged passionate kisses. Britney went first, then Xtina, and, as the audience lost its collective mind, show producers were smart enough to cut to a shot of Spears’ ex, Justin Timberlake … who, needless to say, didn’t have quite the same reaction. He was about the only person in America who felt that way, of course.

Understandably, it took a few years before anyone could come close to topping that moment, though several folks tried (Diddy opened the ’05 show with a “Matrix” like dance routine, and Jay-Z announced he was the King of New York from high atop Rockefeller Plaza the following year). Even Spears would have another go, though her somnambulant ’07 “performance” of “Gimme More” is probably best remembered for the reaction shots it inspired … the stars in attendance couldn’t believe what they were seeing, and not in a good way.

No, it wasn’t until the 2011 VMAs that another superstar mounted a serious challenge to “The Kiss” … Lady Gaga — Jo Calderone — opened the show with a lengthy performance-art monologue, one that saw her violate several California anti-smoking laws, guzzle beer, and somehow manage to work an epic version of “You and I” into the mix, one that featured several dancers and Queen guitarist Brian May (because, hey, why not?) Gaga has been no stranger to over-the-top VMA moments in the past, but this one took the cake.

Then again, Gaga just announced that she’ll open the 2013 MTV Video Music Awards with her first live performance of “Applause,” and we’re pretty sure she’s going to pull out all the stops. What does she have in store for us? Find out this Sunday, when the VMAs air live at 9 p.m. ET from the Barclays Center in Brooklyn.

Make sure you tune in early … as history has shown, you definitely don’t want to miss the opening act!