Howard Stern, for his part, has said he’s supporting Clinton in the presidential election. "I don't dislike Trump as a candidate," he told the Washington Post, "but I am absolutely enamored by Hillary. And I've told Donald that."
While promoting the Miss USA pageant in 2005, Trump told the shock jock, "If you're looking for a rocket scientist, don't tune in tonight. But if you're looking for a really beautiful woman, you should watch."
Shortly after Trump married wife #3, Melania, in 2005, he talked about wanting to have more children… with one condition: "I mean, I won't do anything to take care of them. I'll supply funds and she'll take care of the kids. It's not like I'm gonna be walking the kids down Central Park."
"It looks like she had the lips pumped," Trump said of Anna Nicole Smith. "For all of your many women listening, why do women have their lips pumped? It is the most disgusting thing to look at these big fat pumped up tires."
"I never thought she was good-looking," Trump said of beauty, Angelina Jolie. "I don't think she's got good skin. I don't think she's got a great face. I think her lips are too big, to be honest with you, they look like too big."
A few months after Princess Diana was killed in an automobile accident, Trump told Stern he would have slept with her "without hesitation" and that "she had the height, she had the beauty, she had the skin." He added, "She was crazy, but these are minor details."
Playboy magazine model Carmen Electra had a body that scored low with Trump, who said on Stern's radio show, "The boob job is terrible — they look like two light posts coming out of a body."
During the height of "Desperate Housewives" popularity, Trump rated the female cast on a scale of 1 to 10 based on their attractiveness. He said of Nicollette Sheridan, "A person who is very flat-chested is very hard to be a 10."