By Sara Vilkomerson
Updated April 13, 2015 at 05:07 PM EDT
Credit: Christopher Polk/Getty Images

There are very few things as excruciating to watch as an awkward kiss. But when said kiss is a big, messy, can’t-look-away-even-though-you’re-desperate-to affair? Shudder. With Madonna and Drake joining the ranks of the all-time most awkward onstage kisses, we thought we’d round up a few of our other favorites.

DRAKE AND MADONNA, April 12, 2015

On Sunday night, Madonna—whom we can always count on to keep things real, and weird, and real weird—made a surprise appearance at Drake’s performance at Coachella. The rapper was performing the song “Madonna” off his latest album If You Are Reading This It’s Too Late when Her Madgesty strode out, wearing a tank emblazoned with a lyric from Drake’s song. She then seemingly shocked the stuffing out of Drake when she tilted his head back and planted one on him. And we mean planted—wasn’t the best/worst part when Drake lifted a hand up to Madonna’s head and she swatted it away? It certainly didn’t seem staged, judging by the look on Drake’s face when she released it. He said, “Oh, shit. What the f–k just happened?” Madonna— who told Us Weekly last month that the only ambition she wanted to fulfill was to go on a date with Drake and kiss him—said simply, “I’m Madonna, bitch.” True.


At the 75th annual Academy Awards, Halle Berry announced that Adrien Brody had won the Best Actor award for his performance in The Pianist. The actor leapt out of his chair, got to the stage, and scooped Berry up into an over-the-top embrace—plus an impulsive (and not exactly clearly consensual) make-out session. The actress, when finally allowed to come up for air, looked understandably stunned. “I bet they didn’t tell you that was in the gift bag,” Brody said to Berry, who gamely smiled and tried to fix her lipstick.

AL AND TIPPER GORE, August 17, 2000

At the Democratic National Convention, Al Gore broke from political convention when he greeted his wife, Tipper, and planted a big ol’ kiss lasting nearly three seconds. By MTV standards, this is snooze city—but for the C-span set, we’re talking major bells and whistles. Gore almost managed to convince the nation that he had a human side to him; unfortunately, he and Tipper separated in 2010.


The 1994 MTV Video Music Awards opened with a public declaration of coupledom between Michael Jackson and Lisa Marie Presley. It’s debatable which is tougher to watch—the standing awkwardly, or the 1-2-3-go quality of this truly weird kiss. “And just think, nobody thought this would last,” Jackson said to his future bride. Spoiler: It didn’t.