Donald Trump said in a 2004 interview with Howard Stern about Lindsay Lohan that "deeply troubled" women are "always the best in bed," according to a CNN KFile review of the appearance.
In the hours of crude and misogynistic sex talk Trump engaged in when he appeared on The Howard Stern Show, one of the most common topics of discussion were famous women.
Trump and Stern would often rate, rank, and describe in sexual terms female celebrities. In appearances reviewed by CNN's KFile, Trump also told Stern he would pay not to receive oral sex from Rosie O'Donnell and teased a recently-deceased Anna Nicole Smith for her large lips.
A Trump campaign spokesperson did not respond to a request for comment on this story.
The GOP nominee has faced widespread criticism for his past comments on women and sex. Last Friday, a 2005 "Access Hollywood" tape surfaced in which Trump, caught on hot mic, bragged about forcing himself on women and grabbing them by their genitals. Trump issued an apology for the comments in a video statement, but has continuously referred to the exchange as "locker room talk."
CNNs KFile reported on Saturday that Trump, on Stern's show, approved of the radio shock jock calling his daughter, Ivanka, a "piece of ass" and described how he would go backstage at his pageants while contestants were naked. The Trump campaign has not responded to a CNN request for comment on that story.
On Lindsay Lohan:
In an appearance on Stern's show in December 2004, Trump initiated a conversation about actress Lindsay Lohan, who was 18 at the time.
"What do you think of Lindsay Lohan?" Trump asked Stern.
"I think she's hot," responded Stern.
"There's something there right?" Trump said. "But you have to like freckles. I've seen a, you know, close up of her chest and a lot of freckles. Are you into freckles?"
"I'm not into freckles, but the red hair thing I like. I like her on the cover of Entertainment Weekly," said Stern.
"Now does the father wreck, does that bother you a little bit?" Trump asked later in the conversation.
"Howard feels that the father being a wreck is a good thing," interjected co-host Robin Quivers.
"Oh yeah, because first of all, if the father's a wreck like the way he is--" Stern said.
"Right," said Trump.
"Can you imagine the sex with this troubled teen?" said Stern.
"Yeah, you're probably right," Trump said. "She's probably deeply troubled and therefore great in bed. How come the deeply troubled women, you know, deeply, deeply troubled, they're always the best in bed?"
Stern responded, "Because they're looking for love, they're looking for positive affirmation, they're looking for a father figure who will love them and tell them they're wonderful and they'll never be enough. No matter how many times you tell them they're beautiful, no matter how many times you tell them you love them they want to suck it up more. They would drain you like a vampire until your head caved in if they could get more love."