The presidential hopeful initiated the conversation, asking Stern what he thinks of the then 18-year-old actress. “I think she’s hot,” Stern responded.
“There’s something there right?” said Trump. “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?”
Stern answered that he is “not into freckles” and later asked Trump if he could imagine “having sex” with the “troubled teen.”
Trump responded, “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?”
In response the comments, Hunter Frederick, a representative for Lohan tells PEOPLE, “Donald Trump is a perfect example that money cannot buy you class. As a man, I am disgusted.”
The rep also issued a statement on behalf of Lohan, saying, “Right now, Lindsay is choosing to focus on the positive things happening in her life and has decided to disregard the comments made about her by Presidential nominee Donald Trump. She is focusing on helping children around the world in need and that’s where her passion is.”
In the interview, Trump also commented on Lohan’s father, Michael Lohan, asking Stern, “Now does the father wreck, does that bother you a little bit?” Co-host Robin Quivers interjected, “Howard feels that the father being a wreck is a good thing.”
Later, Trump recalled a friend of his who has a preference for “crazy women” saying, “Well I have a friend Howard who’s actually like a great Playboy, I mean, I don’t say this about men, this guy does very well. He runs silent, runs deep as they say, like a submarine. He will only look for a crazy women. He says, ‘Donald, Donald, please, please, I only want the crazy women.’ “
“They’re desperate,” offered Stern.
“But for some reason, what I said is true,” Trump added. “It’s just unbelievable. You don’t want to be with them for long term, but for the short term there’s nothing like it.”
According to CNN, Trump often discussed female celebrities in sexual terms during his numerous appearances on the shock jock’s radio show, including telling the host he would pay not to receive oral sex from Rosie O’Donnell and commenting on the recently-deceased Anna Nicole Smith’s “large lips.”
WATCH: GOP Donors Cut Ties with Donald Trump
In another newly unearthed video from The Howard Stern Show, the GOP nominee can be seen laughing after he’s called a “sexual predator” during a 2006 interview alongside his children Ivanka and Donald Jr.
Trump has come under fire after The Washington Post published a video of the presidential candidate making lewd comments about groping and trying to have sex with women during a 2005 conversation with Access Hollywood’s Billy Bush that was caught on a hot microphone.
Bush has been suspended from his position as a co-host on the Today show.
Trump dismissed his comments as “locker room talk” and released a video-taped apology, although he has denied that he has ever made any unwanted sexual advances toward women.
In the wake of the tape’s release, Trump has faced assault accusations from several women claiming the presidential nominee touched them inappropriately without their permission. The New York Times reported two of the claims, and Trump has since strongly denied the accusations and called for the publication to retract the report.
A former PEOPLE reporter has also shared her story of being physically attacked by Trump, an allegation Trump has also vehemently denied.
In a fiery speech in Florida on Thursday, Trump continued to deny the claims, calling them “totally and absolutely false,” and vowing to sue the Times.