2016

HEIDI KLUM

In a rare case of setting himself up for his own gaffe, in August 2015, Trump told The New York Times that, "Sometimes I do go a little bit far," when talking about women, before adding, "Heidi Klum. Sadly, she's no longer a 10." Klum, 42, responded with a video of a man in a Trump mask ripping a "10" sign off her chest to reveal one that reads "9.99." Checkmate.