5 Ashlee Simpson’s Lip Sync Sink
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The singular most memorable moment in Ashlee Simpson’s career was the time she was caught in a Milli Vanilli moment, lip synching on stage…and not just anywhere, but on "Saturday Night Live," the show that has always prided itself on, uh, live performances. The audience heard Simpson's prerecorded voice singing while she held the microphone at her waist. The 2004 incident was made even more embarrassing by the way Simpson handled it—dancing a goofy little jig before running offstage, and then trying to blame her band for accidentally playing the wrong song. Bad excuse because even if a whole band could possibly make that ridiculous mistake, it wouldn’t include her disembodied vocals. “I made a complete fool of myself,” she later said. Yup, got that one right!
4 Fergie’s Stage Wetting
So you think barfing on stage is bad? Wait, this is definitely worse…peeing your pants on stage. That’s what Black Eyed Peas singer Fergie did during a 2005 San Diego concert. “I was late, so I didn’t go to the restroom before I went on stage,” she offered as a lame excuse. “It was horrible, but whatever, it happened.” Come on now, Fergie, there’s always time for a pit stop before climbing onstage. And if you just can’t hold it, that’s what drum solos are for!
3 Justin Bieber’s Public Puke
Male celebs don’t seem to do as many epic embarrassing things as the ladies. They don’t have the same opportunities for wardrobe malfunctions, and when they do screw up they pretend they actually meant to do it. Justin Bieber, on the other hand, makes up for his brethren. From hoping Anne Frank would have been a “Belieber” to calling the Sistine Chapel the “Sixteenth Chapel,” he puts his foot in his mouth often. In the fall of 2012, he let everything out of his mouth when he puked onstage during a concert in Phoenix. He blamed it on guzzling whole milk with spaghetti sauce (huh?).
2 Britney Spears’ Crotch Watch
What’s worse—or at least as bad—as being topless on the red carpet? Being bottomless on a night out. Going pantyless and flashing paparazzi while getting out of cars has become almost de rigeur among the drunken starlet set. But Britney Spears was the first to make a spectacle of her nether regions while out partying with Paris Hilton in 2006, and her name will forever be linked with that kind of behavior. Oh, and in case you missed all the pictures of that first really embarrassing time, Spears made sure to give encores of her flash mob performance repeatedly. Kind of gives new meaning to her song “Oops! ... I Did it Again.”
1 Tara Reid’s Nip Slip
OK, it was more than a nip. Actress Tara Reid’s whole left breast decided it wanted to be part of the red carpet photo shoot at Diddy’s 35th birthday bash in 2004. And it sure made the most of that limelight moment—Tara’s wardrobe malfunction was snapped by countless press photographers for several long seconds before a frantic handler…uhh, handled her by pulling up her dress. Reid admits to being clueless about it, saying, “You can tell I don't even know what's happening. I'm just standing there, smiling like an idiot with her boob out.” And yes, this is now what Tara is known for above all else.