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Like it or loathe it, Playboymagazine has played an iconic role in American pop-culture history. Still, few are likely to consider it "presidential."

News broke Friday that Republican presidential nominee Donald Trump once appeared in a soft-core porn film called Centerfolds, which was produced by Playboy and released in 2000.

Surprisingly, or perhaps unsurprisingly when it comes to Trump, his history with the magazine goes much deeper.

Trump's appearance in the explicit flick is reportedly minor: He's shown pouring champagne on a Playboylogo. But other parts of the film include "'fully nude' women touching each other sensually and rubbing honey on themselves," according to BuzzFeed, which obtained the movie from an online-only adult video store based in Buffalo, New York.

It turns out the 2000 honey-rubbing film is just the beginning of Trump's direct and indirect history with Playboy. Here's a brief rundown, starting with Friday's revelation.

"Check out sex tape"

Tweet may have been deleted

"Check out sex tape," Trump tweeted in the wee hours of Friday morning.

He was attempting to smear Alicia Machado, the former Miss Universe he is alleged to have demeaned by calling "Miss Piggy" and "Miss Housekeeping" after she won the beauty contest in 1996.

Trump did not provide any evidence of such a tape, though, and his tweet storm was quickly followed by Friday's news about Trump appearing in that 2000 Playboyflick. In the absence of any further evidence, it appears Trump in fact has more of a so-called sex-tape history than most.

Ivanka Trump's "very nice figure"

In 2006, Trump and his daughter Ivanka appeared on The Viewto promote his reality show, The Apprentice. Trump was asked what his reaction would be if Ivanka were to appear in Playboy.

His answer was super creepy.

"I don't think Ivanka would do that inside the magazine," Trump said, in reference to Ivanka hypothetically posing nude. "Although she does have a very nice figure. I've said that if Ivanka weren't my daughter, perhaps, I would be dating her."

Oh my. He went there.

Which brings us to the time Trump appeared on Howard Stern's radio show and lamented that Ivanka had made him promise never to date anyone younger than her.

"So as she grows older," Trump told Stern, "the field is getting very limited."

Trump was 52 at the time; Ivanka was 17.

They also posed for one of the creepiest father-daughter portraits ever.

Tweet may have been deleted

But we digress. Back to Playboy.

A prominently placed cover

Trump appeared on the cover of the March 1990 issue of Playboy. It apparently featured prominently in his office as recently as July.

We know this because it's pretty obviously in the background of a photo posted to Twitter by Jerry Fallwell Jr. He's the son of evangelical leader Jerry Falwell and the president of Liberty University, an evangelical institution.

Tweet may have been deleted

You can see the framed cover just over the left shoulder of Becki Tilley, Fallwell Jr.'s wife. Predictably, the photo did not sit well with many of Fallwell Jr.'s followers.

Here's a closer look at that cover, by the way.

Tweet may have been deleted

There was an interview, too ...

The introduction to the interview with Trump contained in that 1990 Playboyissue begins with an opening line that's darkly funny given his middle-of-the-night sex tape tweet about Machado.

"Donald Trump sits alone," the 1990 article begins. "He hasn’t slept in 48 hours."

He was also pushing a line 26 years ago that sounds quite familiar today.

Trump told interviewer Glenn Plaskin that "I hate seeing this country go to hell. We’re laughed at by the rest of the world."

Perhaps some things, as they say, never change.

Um, thanks for sharing?

From the Washington Postearlier this year:

When asked by Playboymagazine in 2004 about Viagra, Trump boasted: "I just have never needed it."

He went on to say that what he really needed was an "anti-Viagra, something with the opposite effect."

"I’m not bragging," he bragged. "I’m just lucky."

The "anti-Viagra," LOL. (Trump, of course, is known to lie quite often.)

"Which of these girls are yours, and which ones are mine."

Surya Yalamanchili is a former contestant on The Apprentice. Writing for Politicoin April, Yalamanchili recounted one of his experiences with Trump.

As a "reward" for doing well in the show's competition one week, Trump took Yalamanchili's team on a trip to the Playboy Mansion. At one point, Trump, Playboyfounder Hugh Hefner and Yalamanchili's group went outside, where a surprise pool party had been staged. The party featured "dozens of women — some wearing bikinis, others sporting bunny ears and bowties."

We'll let Yalamanchili take it from here.

"Toward the end of the evening, I found myself in a small circle, conversing with Trump, Hefner and another contestant," he writes. "With a wry smile, Trump looked at Hefner and said, 'It’s hard for me to tell which of these girls are yours, and which ones are mine.'

"The women on my team were well-credentialed business executives, people Trump had supposedly hand-picked for their skills. 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."

Presidential? We'll let you decide.

Temperament: "Too livid to speak"

Writer Mark Bowden profiled Trump for Playboy in 1996, and recounted his experience in a piece for Vanity Fairlast December.

In short, they had an awkward time together, Trump came off as a jerk and at the end of Bowden's visit both men "knew he probably wouldn’t like the final product."

When the article did come out, however, Bowden got a call from Trump's assistant at the time, a woman named Norma Foerderer. Here's how Bowden recounts their exchange.

"Mr. Trump would like to talk to you," she said.

I waited, sitting on the edge of my bed, bracing myself.

Foerderer came back on the line. She said:

"He's too livid to speak."

Trump's temperament, of course, is a major topic of debate during this election.

"Too livid to speak" and "nuclear launch codes," some might argue, are not necessarily things one wants in the same sentence when it comes to the presidency.

Polaroid player

On May 3, 1993, Trump attended the 40th anniversary party for Playboy. While there, he apparently took some photos of models on a Polaroid camera, which gives us these retro gems.

Seems to be enjoying himself.

What are you looking at, Donald?

Trump also attended Playboy's 50th anniversary party in 2003. The woman to his right, with whom Trump seems to be quite impressed, is Playboy model Victoria Silvstedt. The woman to his left is Melania Knauss, now known as Melania Trump, whom he'd marry two years after this photo was taken.

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