Throwback: When Justin Timberlake Watched Britney Kiss Madonna

Britney Spears kisses Madonna on stage.

Getty Images Britney Spears & Madonna lock lips at the 2003 MTV Video Music Awards at Radio City Music Hall on August 28, 2003 in New York City.

The 2003 MTV VMAs featured one of the most talked about moments in award show history; the moment when Britney Spears kissed Madonna. The moment was so over-the-top, in fact, that many people don’t even care that Madonna also locked lips with Christina Aguilera right afterwards.

At the time, just about everyone was elated to see the performance of a lifetime. The performance married three of the biggest entertainers in the world and had people in complete shock. One of the most talked about reactions following the kiss-heard-round-the-world was that of Justin Timberlake’s, Britney’s ex-boyfriend.

At the time, one of the camera crew members zoomed in on Justin, who looked less than impressed and a bit uncomfortable.

Britney and Justin split in 2002 after dating for nearly four years. Things didn’t end well for the couple and the end of their romance was laced with cheating rumors. Justin supposedly turned to his music to cope with the love loss and betrayal, penning “Cry Me a River” which has long-been believed to reveal the real reason behind the breakup. Justin even had a Britney look-alike in the music video. In 2003, Britney responded with her very own song. “Everytime” has long been known to fans as her public apology to Justin.

Here’s what you need to know:


Justin Timberlake’s Face as He Watched Britney Kiss Madonna Was Priceless


Beso Britney y MadonnaBueno..subo este video,porke fue uno de los mejores premio ke eh visto en mtv. Me gusto ☺ espero a uds tambien..2009-06-09T20:34:30Z

Britney and Christina were wearing white wedding gowns when they appeared on stage next to Madonna, who wore all black for the performance. The crazy kiss happened during a rendition of Madonna’s song, “Hollywood,” which was towards the end of the rehearsed medley.

“Everybody comes to Hollywood, they wanna make it in the neighborhood. They like the smell of it in Hollywood, how could it hurt you when it looks so good?” Madonna sang into the microphone as she seductively interacted with both Britney and Christina. As she sang the very last line, she lifted Spears’ face to her own and the two shared a steamy smooch.

The camera quickly panned to Justin, who didn’t show very much emotion but looked a bit uncomfortable. You can see Justin’s reaction at the 3:57 mark in the video above. After the kiss, Missy Elliot came out to keep the epic performance going.


Justin Later Talked to Access Hollywood About the Britney/Madonna Kiss


Justin Timberlake Talks About Britney Spears & Madonna2019-02-05T13:42:35Z

After the kiss went down, Justin chatted with Pat O’Brien from Access Hollywood and explained his somewhat strange reaction.

When asked what he thought of the opening number, Justin said “it was very glossy.”

Then Pat said that he “loved the expression” on Justin’s face “when they kissed.”

“Come on, man. Well, the expression came from the fact that the cameras were, you know, right after the kiss, they were like…” Justin said, making a zooming-in motion. “And I was like, come on. Come on.”

Pat went on to ask if Justin thought it was sexy.

“It’s always sexy. I’m not going to take that away from anybody up there,” he said.

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