Donald Trump’s Gross History of Negging Angelina Jolie

He once called her "a seven."

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Angelina Jolie‘s agent is probably going to spend the better part of the next decade turning down offers for his client to play Melania Trump is the various Trump-themed limited series and movies Hollywood has in the works. And as intriguing as the possibility of that casting could be, don’t expect Donald Trump himself to disagree. Contributing to the caches of Trump’s frequent lapses of logic, Trump has had longstanding issues with one of America’s most beloved stars. A history that Howard Stern resurfaced while guesting on David Letterman’s Netflix chat show.

Before moving into politics, Trump was a recurring guest on Stern’s radio program, and Stern says he was perfect for the format because he could ask the businessman any question and he’d just rant on about it no matter what the topic. “A guest who comes on and says anything that is in his mind is a great guest, and he would get on and no matter what I asked him, he would answer in a very sincere and thought-out way,” Stern said. Even if those questions didn’t really warrant a very sincere and thought-out answer.

“I’d say, Mr. Trump, who are the great beauties? If I ask you some names, can you tell me who the great beauties are?”

“First of all, the great beauties aren’t actresses. It’s models and a lot of these girls who work in the…anyone who works in the entertainment industry, I’ve only seen sixes and sevens,” is how Stern paraphrased his response.

“So, you know, I’d say, Donald, I think Angelina Jolie is a great beauty,” Stern continued.

“Seven!” Trump replied. “He goes, ‘You know who is a great beauty? My daughter Ivanka. She’s a 10.”

If Trump was on a “Now you know what kind of woman I really think is a perfect ten? One who can make me laugh” tip, maybe we could perhaps let him slide here. But he was being completely serious and drilling down on the boorish practice of rating women’s looks on a scale. Even if he had rated Jolie a 10, it would have been inappropriate, but Jolie was once voted “World’s Most Beautiful Woman” by readers of Vanity Fair, after all.

Turns out, however, Trump’s odd fixation with Jolie extends beyond the impromptu rating on Stern. Back in 2007, while guesting on CNN’s Larry King Live, he also unleashed on the actress.

“Angelina Jolie is sort of amazing because everyone thinks she’s like this great beauty,” he told King. “And I’m not saying she’s an unattractive woman, but she’s not a beauty, by any stretch of the imagination. In terms of beauty, she’s not a great beauty. She’s a nice-looking woman. She’s okay. But she’s not a great beauty.”

He then proceeded to slut-shame her.

“I remember at the Academy Awards a few years ago she was frenching her brother. She was giving her brother lip kisses like I never saw before in my life. And she had just said she made love to Billy Bob Thornton in the back of the limousine on the way over,” Trump explained. “And I wouldn’t want to shake her hand, by the way.”

Standard Trump fact-check: Jolie’s quip about a romp in a limousine happened at the 2000 premiere of Gone in 60 Seconds, and not at the Academy Awards. She also did not “french” her brother. In any event, Trump brought up these dumb tabloid-concocted scandals seven years after the rest of the world had moved on, but he couldn’t let it go.

“And now she’s like a representative of the United Nations and world peace on hunger and all of this crap,” he told King. “It’s called, give me a break.”

“She’s been with so many guys she makes me look like a baby, okay,” he also said.

Trump did give eventually her “credit” for her charity work, and did so again in 2013 when he took to Twitter:

Even when he’s trying to compliment Jolie, he has to remind everyone that he doesn’t approve of her past. When really it seems the past we should disapprove of is the fact that multiple straight white men with established programs and huge audiences (one of which was on an actual news network in a prime-time slot) has let Donald Trump come on and give his unchallenged and unfiltered takes on what he thinks about women’s bodies and lives. Because he was an easy interview.

Jolie has never directly replied to Trump’s thoughts on her life or appearance, but an op-ed she wrote for The New York Times in February 2017 about the international refugee crisis did seem to come in response to the Trump administration’s ill-fated travel ban.

“I’m proud of our country’s history of giving shelter to the most vulnerable people,” she wrote. “Americans have shed blood to defend the idea that human rights transcend culture, geography, ethnicity, and religion. The decision to suspend the resettlement of refugees to the United States and deny entry to citizens of seven Muslim-majority countries has been met with shock by our friends around the world precisely because of this record.”

Yet Trump was the one constantly invited on cable news to blather on about what sort of women he finds attractive.

Related: Angelina Jolie, Renaissance Woman, Can Also Fly and Land a Plane