01of 10HEIDI KLUMFrazer Harrison/GettyIn 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.

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HEIDI KLUM

Frazer Harrison/Getty

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.

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MEGYN KELLY

Andrew Harnik/AP; Getty

MEGYN KELLY

03of 10

ROSIE O’DONNELL

Nicholas Hunt/Patrick McMullan/Sipa USA

HEART TO HEART

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ANGELINA JOLIE PITT

Taylor Hill/Getty Images

ANGELINA JOLIE PITT

05of 10HILLARY CLINTONNCNAOstensibly Trump’s number-one competition for the 2016 presidency, Hillary Clinton has seen her fair share of attacks from the Donald.On Twitter alone, he’s called her a liar, “weak,” “sad,” “totally incompetent,” “pathetic,” and “inefficient.”

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HILLARY CLINTON

NCNA

HILLARY CLINTON

Ostensibly Trump’s number-one competition for the 2016 presidency, Hillary Clinton has seen her fair share of attacks from the Donald.On Twitter alone, he’s called her a liar, “weak,” “sad,” “totally incompetent,” “pathetic,” and “inefficient.”

06of 10SARAH JESSICA PARKERMediaPunch/REXFor reasons known only to him,Trump took to Facebook to say he agreedwithMaximbranding Sarah Jessica Parker the “unsexiest woman alive” in 2007. In the same post, Trump wrote about Parker’s refusal to comment on a charitable gift she’d made toBarack Obama’s campaign. Parker had said commenting it was “beneath her;” in his post, Trump wondered, “What’s really beneath her?”

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SARAH JESSICA PARKER

MediaPunch/REX

Image

For reasons known only to him,Trump took to Facebook to say he agreedwithMaximbranding Sarah Jessica Parker the “unsexiest woman alive” in 2007. In the same post, Trump wrote about Parker’s refusal to comment on a charitable gift she’d made toBarack Obama’s campaign. Parker had said commenting it was “beneath her;” in his post, Trump wondered, “What’s really beneath her?”

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CHER

Jamie McCarthy/FilmMagic

CHER

08of 10GAIL COLLINSJamie McCarthy/WireImageWe’ll just letNew York Timescolumnist Gail Collins describe their interactionsin her own words: “During one down period, I referred to him in print as a ‘financially embattled thousandaire’ and he sent me a copy of the column with my picture circled and ‘The Face of a Dog!’ written over it.”

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GAIL COLLINS

Jamie McCarthy/WireImage

GAIL COLLINS

We’ll just letNew York Timescolumnist Gail Collins describe their interactionsin her own words: “During one down period, I referred to him in print as a ‘financially embattled thousandaire’ and he sent me a copy of the column with my picture circled and ‘The Face of a Dog!’ written over it.”

09of 10BETTE MIDLERGilbert Carrasquillo/FilmMagic"Bette Midler talks about my hair but I’m not allowed to talk about her ugly face or body – so I won’t. Is this a double standard?“Trump tweetedin 2012,before continuing, “While Bette Midler is an extremely unattractive woman, I refuse to say that because I always insist on being politically correct.”

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BETTE MIDLER

Gilbert Carrasquillo/FilmMagic

BETTE MIDLER

“Bette Midler talks about my hair but I’m not allowed to talk about her ugly face or body – so I won’t. Is this a double standard?“Trump tweetedin 2012,before continuing, “While Bette Midler is an extremely unattractive woman, I refuse to say that because I always insist on being politically correct.”

10of 10ARIANNA HUFFINGTONMichael Kovac/WireImage"Arianna is unattractive both inside and out,“Trump tweeted in 2012. “I fully understand why her former husband left her for a man – he made a good decision.”

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ARIANNA HUFFINGTON

Michael Kovac/WireImage

ARIANNA HUFFINGTON

“Arianna is unattractive both inside and out,“Trump tweeted in 2012. “I fully understand why her former husband left her for a man – he made a good decision.”

source: people.com