18. Miley Frees the Nipple (2015)
"Oh, sorry, my tit's out?" Miley Cyrus asked coyly. It was only a matter of time before the "Free the Nipple" activist suffered a lack-of-wardrobe malfunction sometime during the 2015 VMAs. The camera tried to stop it — it cut away a few times — but it came in like a wrecking ball.