Inside Trump's History with 'Playboy' as It Preps to Make White House Correspondents' Dinner Debut  

From parties at the Playboy Mansion to his cameo in a soft-core porn film, Donald Trump's history with Playboy and its late founder Hugh Hefner is long and storied

Photo: Sipa Press/REX/Shutterstock

Nerd Prom is getting a new after-party.

Playboy magazine has announced that it will host its first-ever after-party following the White House Correspondents Dinner in Washington, D.C., this Saturday.

The event will be hosted by Cooper Hefner, son of the late Playboy founder Hugh Hefner, at a downtown Washington nightclub. Hefner and several unnamed guests will also have a coveted table at the glitzy black-tie correspondents’ dinner itself — prompting some to wonder whether one of those mystery guests could be former Playboy Playmate Karen McDougal, who claims she had an affair with President Donald Trump in 2006. (A media rep for Karen McDougal’s attorney, Peter Stris, told PEOPLE that McDougal is not attending and was not invited.) Trump, who has denied the affair, is also skipping the dinner, as he did last year.

A rep for Playboy promises there are surprises in store for the after-party, which will be attended by celebrities and journalists, including Jim Cramer, Don Lemon, Jim Acosta, Dana Bash and Scott Wapner.

McDougal is not Trump’s only Playboy connection — far from it.

From parties at the Playboy Mansion to his cameo in a soft-core porn film, Trump’s history with the magazine and its late founder is long and storied.

It all started nearly 30 years ago, when Trump appeared on the cover of Playboy‘s March 1990 issue.

On the cover, a smirking Trump poses next to a woman clad in only his suit jacket. “Nice magazine. Want to sell it?” reads the caption next to Trump.

Inside, the future president bemoans the state of the country in an interview. “I hate seeing this country go to hell,” he said. “We’re laughed at by the rest of the world.”

Playboy Magazine

Trump has come a long way from the Playboy Mansion to the White House, but he’s apparently still proud of his cover issue, which was on prominent display in his Trump Tower office as recently as June 2016.

You can see the framed cover in the above photo of then-GOP hopeful Trump posing with Jerry Fallwell Jr., the son of evangelical leader Jerry Falwell, and his wife, Becki Falwell.

Sara D. Davis/Getty

And here’s the then-presumptive Republican presidential nominee showing off his cover coup for a police officer during a campaign event in Raleigh, North Carolina, on July 5, 2016.

1993

Trump attended the 40th anniversary party for Playboy on May 3, 1993. While there, he snapped some photos of (clothed) models on a Polaroid camera and conducted interviews in the search for Playboy‘s 40th anniversary Playmate.

Ron Galella/WireImage

1998

Trump attended Playboy‘s 45th anniversary party, where he posed with several Playmates.

Richard Corkery/NY Daily News Archive/Getty

2000

Trump notably appeared in the soft-core porn film Centerfolds, which was produced by Playboy and released in 2000. Trump’s cameo, in which he pours a bottle of champagne on a Playboy-branded limo, does not include any nudity. But other parts of the film feature “fully nude women posing in sexual positions, dancing naked, touching themselves while naked, touching each other sensually, rubbing honey on themselves, taking a bath, and dressing in costumes,” according to BuzzFeed, which obtained the movie from an online-only adult video store.

The video came back to haunt Trump during the campaign, after he attacked former Miss Universe Alicia Machado for her “sex tape,” which was actually a video of her having sex while appearing on a reality show.

2003

Trump attended Playboy‘s 50th anniversary party in 2003, where he was accompanied by his future wife, Melania Trump, then Melania Knauss. The Trumps were photographed with Hefner and his then-girlfriend and co-star on The Girls Next Door, Holly Madison, as well as Playboy model Victoria Silvstedt.

Getty

Sipa Press/REX/Shutterstock

2004

In 2004, Trump boasted to Playboy magazine about how he’s “never needed” Viagra.

He went on to say that what he really needed was an “anti-Viagra, something with the opposite effect,” the Washington Post reported last year.

“I’m not bragging,” he said. “I’m just lucky.”

RELATED VIDEO: Watch: Natasha Stoynoff Breaks Silence, Accuses Donald Trump of Sexual Attack

2006

Trump and his daughter Ivanka appeared on The View in 2006 to promote his reality show, The Apprentice. Asked how he would react to Ivanka hypothetically appearing in Playboy, Trump said, “I don’t think Ivanka would [pose nude] inside the magazine.

“Although she does have a very nice figure,” he added. “I’ve said that if Ivanka weren’t my daughter, perhaps, I would be dating her.”

This year also saw Trump posing for a photo with McDougal, Ivanka and wife Melania at a Playboy Mansion party for Trump’s reality series The Apprentice.

Also in 2006, Trump took several then-Apprentice contestants, including Surya Yalamanchili, and to a party at the Playboy Mansion, where they partied with Hefner and a posse of Playmates.

Andrew H. Walker/Getty

In an April 2016 piece for Politico, Yalamanchili recalled Trump commenting to Hefner at the party: “It’s hard for me to tell which of these girls are yours, and which ones are mine.”

By “his girls,” Trump meant the female Apprentice contestants at the party.

“The women on my team were well-credentialed business executives, people Trump had supposedly hand-picked for their skills,” Yalamanchili wrote. “In that moment, the only real difference to Trump between them and the scantily clad Playmates who were there for his entertainment was that some of the women were ‘his,’ and some weren’t.”

2007

Trump’s eldest son, Don Jr., has also been known to partake in Playboy parties. But he said in 2007 that it was “hell” visiting the mansion with his now-estranged wife Vanessa while she was pregnant with their first child.

In an interview with the The Adam Carolla Show that took place live from the Playboy Mansion in Los Angeles, Don Jr. said at the time: “Can you believe the hell I’m going through? I’m at the Playboy Mansion with a pregnant wife! It doesn’t get worse than that, does it?”

“Now I love my wife, but that is rough,” he continued, before acknowledging that he was “going to pay for these statements later on tonight. I’m going to pay.”

• With reporting by DIANE HERBST