But Trump has also appeared on the shock-jock's show multiple times since the 1990s to field questions about everything from the size of his genitalia to premature ejaculation, sleeping with another man's girlfriend and his wife's bathroom habits. He's also criticized several women for their body shape, described the time he watched a celebrity sex tape, fondly recalled days before the rise in sexually transmitted diseases made condoms necessary and once compared a shrinking economy to a woman's contractions in pregnancy.
Trump's comments on Stern's program, while not out of step with the show's normal fare, reveal further details of the candidate's unvarnished views of women at a time when many Republicans worry that his frontrunner status and larger-than-life persona could further damage the party with female voters before an 2016 election that could come down to the slimmest of margins.
During most interviews, Stern and Trump played a version of "Hot or Not," a game to determine the attractiveness of women.
Prompted by Stern's trademarked blunt questioning, Trump was particularly fond of describing his dislike for reality television star Kim Kardashian's lower body.
Does she have a good body? No. Does she have a fat ass? Absolutely," Trump said of Kardashian, who at one time appeared on his "Celebrity Apprentice" show. "It's record setting," he said in 2014. "In the old days, they'd say she's got a bad body."
"She's got a huge trunk," Trump said in another Stern interview. "It's seriously big."
Other famous women faced similar criticism.
Jessica Chastain is "certainly not hot." Halle Berry is "beautiful" but only her "upper body," Trump said.
"I really like J-Lo," Trump said, referring to Jennifer Lopez. "But that ass is..."
"Scary!" Stern cut in.
Jennifer Lawrence didn't fare well either.
"Jennifer has a little skin problem. A little rough with the skin. I don't quite get it," he said. "Little polka-dots all over the place."
Trump even had harsh words for the house maid who had a secret affair with Arnold Schwarzenegger.
"It was hard to believe," Trump said. "I figured this gorgeous woman with a little black dress...and I said, Well, I guess a thing like that could happen. And then I got to see the maid like everyone else, and I was a little surprised."
On that note, Trump lamented that his wife only hires unattractive service workers in their home. "They're not tens, I can tell you that," he said. "I've been very domesticated. It's a sad event."
As for women Trump does find attractive, Trump pointed to contestants in his "Miss Universe" pageant, particularly women from South America.
"When you look at the Miss Universe people...that's why I'm so jaded," he said. "I see these girls come in from Brazil, from Venezuela. ... You take your best-looking actress in Hollywood, and I'll take, like, Miss Brazil, and you put them next to each other, nobody would even know the other girl's in the room."
He also said he had a fondness for Keira Knightley--"absolutely flawless"--and Paris Hilton--"really beautiful." (Trump added that he did watch a sex tape that featured Hilton, which was leaked onto the Internet.)
Over the years, Trump also took on questions about his own bedroom adventures.
"I went through beauties," Trump said in his 2013 appearance.
Ten years earlier, Trump and Stern mourned the end of the wild days before sexually transmitted diseases necessitated protection.
"We've got to cure AIDS so then we can go back to not wearing rubbers," Stern said.
"Those were the good old days," Trump replied. Remember 1979, Howard?"
In a 2001 interview on Stern's show, he got into a shouting match with gossip columnist A.J. Benza over a women they both dated in the 1990s. As Trump told the story, he stole Benza's girlfriend.
"I've been successful with your girlfriend, I'll tell you that," Trump bragged. "I took her away like he was a dog. ...While you were getting onto the plane to go to California thinking that she was your girlfriend, she was some place that you wouldn't have been very happy with."
Trump and Stern frequently joked about their own sexual successes in misfires. When Stern said he struggled with having intercourse for long periods of time, Trump found a silver lining: "Well that's good in many respects. Then you have to go a second time because it will take a little longer."
On the issues
At times, however, the interviews delved into policy. Stern was especially interested in discussing social issues such as same-sex marriage and abortion, both of which Trump said he opposes, but didn't like to talk about much.
"I'm not saying I wouldn't change," Trump said when Stern pressed him about his opposition to same-sex marriage. "But it hasn't been a subject that has been high on my list, for a lot of reasons."
On abortion, Trump, who said he opposes it with some exceptions, was equally reluctant to discuss the subject.
"It's never been my big issue," Trump said. "Somebody asks me, and I say pro-life, but it's never been an issue that really has been discussed with me in great detail."
When discussing the economy, however, Trump dove right in--with a Trumpesque twist.
"We just had a contraction... like a woman has a contraction," Trump said in 2013 following a sour economic report. "We had a contraction where we actually ceased to grow. We actually got smaller."
Does it matter?
Rhetoric like that hasn't been secret, and hasn't seemed to hurt his campaign.
For most presidential candidates, comments like these would stop a campaign cold. But not Trump, who has successfully used his colorful past--and the media and political class' response--to rally his supporters. For now, Trump doesn't need to play by the same rules as his competitors, and he knows it.
"The big problem this country has is being politically correct," Trump said at last weeks presidential debate when challenged for comments like these. "I've been challenged by so many people and I don't frankly have time for total political correctness. And to be honest with you, this country doesn't have time either."
A Trump spokesperson did not respond to a request for comment on this story.