Former President Donald Trump has had a complicated relationship with Howard Stern and his radio show. There was a time when he'd be a regular guest and pal around with Howard, co-host Robin Quivers, and former co-host Artie Lange. While promoting his 2019 book, "Howard Stern Comes Again", the self-proclaimed King Of All Media stated that interviewing Donald Trump was an absolute experience. He'd never know what he'd say next and that was part of the thrill. Not only was it thrilling, but it made him one of Howard's best guests. While their personal relationship soured due to differing politics and Howard's refusal to endorse Trump for president, the radio legend maintains that the former President was one of his best guests.

Former co-host Artie Lange likely feels the same way even though he too has some issues, albeit not as many, with Donald Trump. Still, the troubled but unbelievably talented comedian clearly had a ball whenever Trump appeared on The Howard Stern Show. But there was one thing Trump said that sent Artie completely over the edge... in uncontrollable laughter...

Donald Trump Claimed That He Gets The Most Beautiful Women And Artie Lange Couldn't Handle It

Regardless of what you may think about the former President's politics or what he did (or didn't do) for The United States, it's really hard to argue that he's humble. The man has a hubris that's just unparalleled. And it was always on full display whenever he'd show up to The Howard Stern Show in the 1990s and early 2000s and talk about women.

Most of Donald Trump's Stern Show appearances occurred prior to Howard's personal and creative evolution where he dropped the shock jock persona and moved toward becoming one of the best celebrity interviewers of all time. So, Howard was game to be as offensive (for the sake of comedy) as humanly possible. But whenever Trump was on his show, all he had to do was sit back and let the man talk. And this is precisely what happened during Trump's September 2004 appearance on The Howard Stern Show.

While speaking about women, Trump made a statement that caused Howard's then co-host to basically laugh in his face. The comment was so outlandish. So out of touch. So unbelievably arrogant... and it was downright funny.

"The National Enquirer did a story on me, not so long ago, [and said] that in the history of the world, 'nobody has got more beautiful women than I have'. Okay? Which is a great compliment", Donald Trump said to Howard, Robin, and Artie who immediately burst out in laughter.

Related: Here's What It Was Like For Howard Stern To Interview Donald Trump

Like many of the extremely arrogant comments that the former President has made, this one was said with utter seriousness. There was no joking in his voice and that's clearly what made Artie Lange lose it.

Artie has seen and met a lot of incredibly handsome men over his lengthy career in show business, and these men have been with an assortment of beautiful women. Donald Trump is not one of these men. While it was, apparently, The National Enquirer who made this pretty crazy comment, which there just no way to prove, Trump repeated it back as though it was a fact. While Howard was happy to let this hilariously boastful comment play out, Artie didn't have the same ability.

What Artie Lange Really Thought Of Donald Trump

Artie has spoken about Donald Trump on a number of occasions. While their political similarities and differences aren't entirely clear, he did have some decently nice things to say about him from his personal experiences. However, not everything was positive as he once described the former President as a guy who could "turn on a dime".

He had this experience when he roasted Trump at a Friar's Club Roast that wasn't televised. While Artie's cutting jokes at the event were well absorbed by Trump, he changed his tune when he appeared on The Stern Show shortly after.

"When he came in as a guest, he got very, very mad, and if you watch both things, it’s hilarious…because his temperament turns on a dime," Artie said, according to The Philly Voice.

Related: The Truth About Howard Stern's Relationship With His Former Co-Host, Artie Lange

Artie recounted this story while being interviewed by Seth Meyers, and pointed out that Howard made him retell some of the roast jokes to Trump's face and they weren't met with the same kindness. When Trump started to attack and insult Artie, Howard tried to calm him down, "It's a joke."

"I don't care, I don't take jokes," Trump responded.

Related: Aubrey Plaza Got Paid $7 An Hour To Do This For Donald Trump

Regardless, Artie was invited to golf with Trump and Eli Manning and claimed that he had a (mostly) good time. While his comments about Trump have been a little inconsistent over the years, Artie seems to be able to laugh at his experiences with the former President.

Next: These Were Artie Lange's Worst Moments On The Howard Stern Show