Hugh Hefner's death recalls one very special Playboy cover

Yahoo News Photo Staff

Burt Reynolds, Jerry Seinfeld, Steve Martin, Donald Trump: What do these men have in common?

All of them are among a handful of men who appeared on the cover of Playboy magazine, founded by Hugh Hefner to celebrate the swinging bachelor lifestyle Trump exemplified, before, between, and occasionally during his three marriages.

Hefner died Wednesday at 91.

Trump’s appearance on the cover of the March 1990 issue — he was the subject of the magazine’s signature long-form interview that month — became one of the future president’s treasured mementos. Fans brought them to campaign rallies for Trump to sign. A framed copy occupied a prominent spot on the wall of his Trump Tower office and appeared in the background of photographs of his meeting with evangelical leader Jerry Falwell Jr. last year.

To those who questioned the propriety of his friendship with Trump, Falwell responded that he was “honored for same hypocrites who accused Jesus of being a friend of publicans and sinners to be targeting me over a decades-old mag cover!”

On the cover, Trump, who was 43 at the time, appears in black tie with a saucy photo of model Brandi Brandt, who had been Playboy’s Miss October in 1987. Her subsequent career was less successful than his; the Washington Post reported last year that she was serving a prison sentence for her role in a cocaine-smuggling ring.

In that 1990 interview, Trump showed flashes of the kind of combativeness that would define his presidential candidacy.

“If somebody is trying to do an injustice to me, I fight back harder than anybody I know,” he said. “When somebody tries to harm you or your family, you have an absolute right to fight back.”

Trump also talked about a business trip to Moscow where he said he met with top-level Soviet officials to discuss potential business deals.

“Generally, these guys are much tougher and smarter than our representatives,” Trump said. “We have people in this country just as smart, but unfortunately, they’re not elected officials. … Some of our presidents have been incredible jerk-offs. We need to be tough.”

The interview then turned to Trump’s political ambitions.

“I don’t want the presidency,” Trump said. “If I ever ran for office, I’d do better as a Democrat than as a Republican — and that’s not because I’d be more liberal, because I’m conservative. But the working guy would elect me. He likes me. When I walk down the street, those cabbies start yelling out their windows.”

“What’s the first thing President Trump would do upon entering the Oval Office?” the magazine asked.

“Many things,” Trump replied. “A toughness of attitude would prevail.”

He was also asked about the glitz and glamour that had come to define him:

“What does all this — the yacht, the bronze tower, the casinos — really mean to you?”

“Props for the show.”

“And what is the show?”

“The show is ‘Trump,’ and it has sold-out performances everywhere. I’ve had fun doing it and will continue to have fun, and I think most people enjoy it.”

– Jerry Adler and Dylan Stableford

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<p>Republican presidential candidate Donald Trump signs a copy of <em>Playboy</em> magazine at a campaign rally in Raleigh, N.C., July 5, 2016. (Photo: Joshua Roberts/Reuters) </p>
Raleigh, N.C., July 5, 2016

Republican presidential candidate Donald Trump signs a copy of Playboy magazine at a campaign rally in Raleigh, N.C., July 5, 2016. (Photo: Joshua Roberts/Reuters)

<p>Republican presidential nominee Donald Trump holds up a <em>Playboy</em> magazine handed to him by a supporter after speaking at a campaign rally in Pensacola, Fla., Sept. 9, 2016. (Photo: Mike Segar/Reuters) </p>
Pensacola, Fla., Sept. 9

Republican presidential nominee Donald Trump holds up a Playboy magazine handed to him by a supporter after speaking at a campaign rally in Pensacola, Fla., Sept. 9, 2016. (Photo: Mike Segar/Reuters)

<p>Republican presidential candidate Donald Trump signs a copy of a <em>Playboy</em> magazine with him on the cover for a memorabilia collector after a rally in Walterboro, S.C., Feb.17, 2016. (Photo: Jonathan Ernst/Reuters) </p>
Walterboro, S.C., Feb.17, 2016

Republican presidential candidate Donald Trump signs a copy of a Playboy magazine with him on the cover for a memorabilia collector after a rally in Walterboro, S.C., Feb.17, 2016. (Photo: Jonathan Ernst/Reuters)

<p>Jerry Falwell Jr. posted a photo of himself with wife Becki and Donald Trump in Trump’s office in Trump Tower on June 21, 2016, in New York City, tweeting, “Honored to introduce @realDonaldTrump at religious leader summit in NYC today! He did incredible job! @beckifalwell.” Trump’s <em>Playboy</em> cover is visible on the wall behind them. (Photo: Jerry Falwell, Jr. via Twitter) </p>
New York City, June 21, 2016

Jerry Falwell Jr. posted a photo of himself with wife Becki and Donald Trump in Trump’s office in Trump Tower on June 21, 2016, in New York City, tweeting, “Honored to introduce @realDonaldTrump at religious leader summit in NYC today! He did incredible job! @beckifalwell.” Trump’s Playboy cover is visible on the wall behind them. (Photo: Jerry Falwell, Jr. via Twitter)

<p>Donald Trump tweeted, “I will be live tweeting my interview with @megynkelly on the Fox Network tonight at 8! Enjoy!” and posted a photo posing with Megyn Kelly in his office in Trump Tower on May 17, 2016, in New York City. His <em>Playboy</em> cover is visible on the wall behind them. (Donald Trump via Twitter) </p>
New York City, May 17, 2016

Donald Trump tweeted, “I will be live tweeting my interview with @megynkelly on the Fox Network tonight at 8! Enjoy!” and posted a photo posing with Megyn Kelly in his office in Trump Tower on May 17, 2016, in New York City. His Playboy cover is visible on the wall behind them. (Donald Trump via Twitter)

<p>Pamela Anderson stands onstage with Melania and Donald Trump to announce the winners in his special “Donald J. Trump Birthday Quarter Million Dollar Giiveaway” celebration on June 11, 2005, in Atlantic City. (Photo: Donald Kravitz/Getty Images) </p>
Atlantic City, N.J., June 11, 2005

Pamela Anderson stands onstage with Melania and Donald Trump to announce the winners in his special “Donald J. Trump Birthday Quarter Million Dollar Giiveaway” celebration on June 11, 2005, in Atlantic City. (Photo: Donald Kravitz/Getty Images)

<p>Pamela Anderson and Donald Trump chat as they attend a special, “Donald J. Trump Birthday Quarter Million Dollar Giiveaway” celebration June 11, 2005, in Atlantic City. (Photo: Donald Kravitz/Getty Images) </p>
Atlantic City, N.J., June 11, 2005

Pamela Anderson and Donald Trump chat as they attend a special, “Donald J. Trump Birthday Quarter Million Dollar Giiveaway” celebration June 11, 2005, in Atlantic City. (Photo: Donald Kravitz/Getty Images)

<p>Holly Madison, Hugh Hefner, Donald Trump and Melania Knauss at the <em>Playboy</em> Magazine 50th Anniversary Party in New York City on Dec. 4, 2003. (Photo: Sipa Press/REX/Shutterstock) </p>
New York City, Dec. 4, 2003

Holly Madison, Hugh Hefner, Donald Trump and Melania Knauss at the Playboy Magazine 50th Anniversary Party in New York City on Dec. 4, 2003. (Photo: Sipa Press/REX/Shutterstock)

<p>Donald Trump is flanked by Victoria Silvstedt, 1997 Playmate of the Year, and his girlfriend, Melania Knauss, at <em>Playboy</em> magazine’s 50th anniversary celebration in New York City on Dec. 4, 2003. (Photo: Richard Corkery/NY Daily News Archive via Getty Images) </p>
New York City, Dec. 4, 2003

Donald Trump is flanked by Victoria Silvstedt, 1997 Playmate of the Year, and his girlfriend, Melania Knauss, at Playboy magazine’s 50th anniversary celebration in New York City on Dec. 4, 2003. (Photo: Richard Corkery/NY Daily News Archive via Getty Images)

<p>Donald Trump with girlfriend Melania Knauss, left, and Kylie Bax attend a party at the Playboy Penthouse in New York City on Sept. 6, 2000. (Photo: Steve Azzara/Corbis via Getty Images) </p>
New York City, Sept. 6, 2000

Donald Trump with girlfriend Melania Knauss, left, and Kylie Bax attend a party at the Playboy Penthouse in New York City on Sept. 6, 2000. (Photo: Steve Azzara/Corbis via Getty Images)

<p>Donald Trump and girlfriend Melania Knauss are joined by a couple of <em>Playboy</em> Bunnies at a launch party for the Hugo Boss store at Fifth Ave. and 56th St. in New York City, circa 2000. (Photo: Richard Corkery/NY Daily News Archive via Getty Images) </p>
New York City, circa 2000

Donald Trump and girlfriend Melania Knauss are joined by a couple of Playboy Bunnies at a launch party for the Hugo Boss store at Fifth Ave. and 56th St. in New York City, circa 2000. (Photo: Richard Corkery/NY Daily News Archive via Getty Images)

<p>Donald Trump talks with a Playboy Bunny during the Betsey Johnson Spring 2001 Fashion Show at Bryant Park in New York City on Sept. 19, 2000. (Photo: Ron Galella/WireImage/Getty Images) </p>
New York City, Sept. 19, 2000

Donald Trump talks with a Playboy Bunny during the Betsey Johnson Spring 2001 Fashion Show at Bryant Park in New York City on Sept. 19, 2000. (Photo: Ron Galella/WireImage/Getty Images)

<p>Donald Trump and playmates celebrate 45 years of <em>Playboy</em> at the Life Club in New York City, Dec. 3, 1998. (Photo: Richard Corkery/NY Daily News Archive via Getty Images) </p>
New York City, Dec. 3, 1998

Donald Trump and playmates celebrate 45 years of Playboy at the Life Club in New York City, Dec. 3, 1998. (Photo: Richard Corkery/NY Daily News Archive via Getty Images)

<p>Donald Trump is flanked by his date, model Melania Knauss, and Jaime Bergman at a party celebrating <em>Playboy</em> magazine’s 45th anniversary at the Life Club in New York City on Dec. 3, 1998. (Photo: Richard Corkery/NY Daily News Archive via Getty Images) </p>
New York City, Dec. 3, 1998

Donald Trump is flanked by his date, model Melania Knauss, and Jaime Bergman at a party celebrating Playboy magazine’s 45th anniversary at the Life Club in New York City on Dec. 3, 1998. (Photo: Richard Corkery/NY Daily News Archive via Getty Images)

<p>Donald Trump snaps a picture of Playmate hopeful Lisa Madison during a publicity session in New York, May 3, 1993. (Photo: Ron Galella/WireImage/Getty Images) </p>
New York, May 3, 1993

Donald Trump snaps a picture of Playmate hopeful Lisa Madison during a publicity session in New York, May 3, 1993. (Photo: Ron Galella/WireImage/Getty Images)

<p>Donald Trump photographs interviewing <em>Playboy</em> centerfold hopeful Bridget during a publicity session in New York, May 3, 1993. (Photo: Ron Galella/WireImage/Getty Images) </p>
New York, May 3, 1993

Donald Trump photographs interviewing Playboy centerfold hopeful Bridget during a publicity session in New York, May 3, 1993. (Photo: Ron Galella/WireImage/Getty Images)

<p><em>Playboy</em> president and CEO Christie Hefner, poses for a photo with Donald Trump and his wife, Ivana, during the 35th anniversary party for <em>Playboy</em> in New York City, Dec. 1, 1988. (Photo: John Barrett/Globe Photos/ZumaPress.com) </p>
New York City, Dec. 1, 1988

Playboy president and CEO Christie Hefner, poses for a photo with Donald Trump and his wife, Ivana, during the 35th anniversary party for Playboy in New York City, Dec. 1, 1988. (Photo: John Barrett/Globe Photos/ZumaPress.com)

<p>Real estate developer Donald Trump with wife Ivana attend a party for 35th anniversary of <em>Playboy</em> on Dec. 1, 1988. (Photo: Robin Platzer/Twin Images/The Life Images Collection/Getty Images) </p>
New York City, Dec. 1, 1988

Real estate developer Donald Trump with wife Ivana attend a party for 35th anniversary of Playboy on Dec. 1, 1988. (Photo: Robin Platzer/Twin Images/The Life Images Collection/Getty Images)

<p>Republican presidential candidate Donald Trump holds up the March 1990 issue of <em>Playboy</em> with him on the cover as he works the rope line after a campaign rally in Farmington, N.H., Jan. 25, 2016. (Photo: Gretchen Ertl/Reuters) </p>
Farmington, N.H., Jan. 25, 2016

Republican presidential candidate Donald Trump holds up the March 1990 issue of Playboy with him on the cover as he works the rope line after a campaign rally in Farmington, N.H., Jan. 25, 2016. (Photo: Gretchen Ertl/Reuters)

<p>A <em>Playboy</em> magazine with a picture of Donald Trump sits on the floor after it was signed by the Republican presidential candidate but failed to reach its owner when it was tossed back into the crowd during a rally at Macomb Community College on March 4, 2016, in Warren, Mich. (Photo: Scott Olson/Getty Images) </p>
Warren, Mich., March 4, 2016

A Playboy magazine with a picture of Donald Trump sits on the floor after it was signed by the Republican presidential candidate but failed to reach its owner when it was tossed back into the crowd during a rally at Macomb Community College on March 4, 2016, in Warren, Mich. (Photo: Scott Olson/Getty Images)

<p>Trump poses on the March 1990 issue of <em>Playboy</em> magazine. (Yahoo News) </p>
Playboy magazine cover, March 1990

Trump poses on the March 1990 issue of Playboy magazine. (Yahoo News)

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