Donald Trump Parties at the Playboy Mansion,a Soft-Core $orn Film and trying to talk Hef into Ivanka Centerfold

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.

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.”

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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.

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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.

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1998

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

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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.

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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.”

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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.”

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.

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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.”

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