2008. "I've been with women with extraordinarily bad breast jobs," he says on Stern's show. "Isn't it unbelievable, one woman, beautiful, had big, beautiful, real boobs, really beautiful, and she wants them reduced. I have never seen a good breast reduction."
October 2007. "Angelina Jolie is sort of amazing because everyone thinks she's like this great beauty. And I'm not saying she's an unattractive woman, but she's not 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 OK. But she's not a great beauty." Trump on CNN's "Larry King Live."
Dec. 21, 2006. "Rosie O'Donnell is disgusting, both inside and out. If you take a look at her, she's a slob." Trump on "Entertainment Tonight."
"How does she even get on television?" he said. "If I were running 'The View,' I'd fire Rosie. I'd look her right in that fat, ugly face of hers and say, 'Rosie, you're fired.'"
2005. "A woman who is very flat-chested is very hard to be a 10." Commenting on actress Nicolette Sheridan on Stern's show.
Jan. 28, 1997. "Some people when they have pressure, they don't eat. And some people when they have pressure eat too much, like me, but like Alicia." Trump at a news conference with Miss Universe Alicia Machado to discuss her weight gain.