17. Lil Mama Crashes Jay Z and Alicia Keys (2009)
Natia "Lil Mama" Kirkland's only major hit, "Lip Gloss," was already two years in the rearview by the time of the 2009 VMAs. There's a good chance MTV wouldn't have even invited her if she wasn't employed by the network as a judge on America's Best Dance Crew. Kirkland got a little caught up in the moment and decided to be part of the show when Jay Z and Alicia Keys performed their chart-topping ode to the Big Apple, "Empire State of Mind." As the song came to a close, Kirkland decided to show her pride as a native New Yorker and join the two superstars onstage, posing in a b-boy stance while a nonplussed Jay Z did his best not to acknowledge her.