Playboy’s Iconic Interviews Come Roaring Back to Life

A new podcast taps the magazine’s historic Q&As, now read aloud by Rosanna Arquette, Natasha Lyonne and other actors
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In his final decade, Playboy founder Hugh Hefner still had big dreams. Inspired by Frost/Nixon, the Tony Award-winning play and, later, a movie about a series of high-anxiety interviews with a disgraced former president, Hef figured he had hundreds of his own dramas just as compelling and ready to go: the monthly Playboy Interview.

“I want to take the Interview to Broadway,” he told Jimmy Jellinek, then the magazine’s editorial director, over lunch at the Playboy Mansion in 2006. “You need to do that.”

Years later, a version of that dream has come true in The Playboy Interviews: Icons & Iconoclasts, a vivid series of dramatizations premiering Thursday on Amazon’s Audible podcast service. The first batch of seven episodes draws directly from the pages of Playboy to re-create some of the most memorable in-depth talks with the heroes and antiheroes of the last half-century, from  Muhammad Ali to feminist icon Betty Friedan, Salvador Dali and Frank Sinatra.

Hefner “understood the power and potential of the material he had,” says Jellinek, now the chief creative officer for Audio Up Media, which produced the series.

The new dramatizations were largely created over four months at Audio Up’s studio, built in a chateau-like home up in Mandeville Canyon. Jellinek turned the interview transcripts into scripts, then produced and directed the episodes, while his partner Jared Gutstadt oversaw the score. The episodes also benefit from some inspired casting, including Natasha Lyonne as a 78-year-old Mae West, Taye Diggs as a young Ali (still called Cassius Clay then by many), Rosanna Arquette as Friedan, and Michael Shannon as Tennessee Williams. “Who doesn’t want to play Tennessee Williams? It wasn’t hard to cast,” Jellinek says, calling the actors “an amazing array of talent we were fortunate enough to work with.”

The Playboy Interview was once among the crown jewels of American journalism, a monthly Q&A with a major figure that frequently made news. Provocative and enlightening, the interviews could run up to 20,000 words, a virtually unheard-of length today for a magazine piece.

Jellinek was at the magazine for more than seven years and reported directly to Hefner, who remained a hands-on leader well into his 80s. Working on the magazine, “was like holding a very precious Faberge egg in your hand. You always wanted to do right by Hef,” says Jellinek. He was the last in a long line of editorial directors that reached back to the magazine’s founding in the 1950s. After Jellinek left in 2015, the magazine hobbled along as Hef retired from the day-to-day operation, and it was never the same. Playboy stopped print publication completely in the U.S. in 2020 and lives on now only as a brand (the magazine is still published in Germany and other foreign territories).

For those who really did read Playboy for the articles, the Interview was a must-read. One vivid example brought to life in Icons & Iconoclasts was a surprising 1963 talk with Sinatra, who weighed in meaningfully on organized religion, communism, global politics and thermonuclear annihilation, mixed with asides on playing craps.

Sinatra seems to be anticipating an era of hair-trigger condemnation from a polarized right and left still a half-century away, when he asks his interrogator: “Can you imagine the deluge of crank letters, curses, threats and obscenities I’ll receive after these remarks gain general circulation? Worse, the boycott of my records, my films, maybe a picket line at my opening at the Sands…” But offered a chance to start over, Sinatra demurs. “Let’s let it run. I’ve thought this way for years, ached to say these things. … I don’t want to chicken out now.”

The monthly interview was one of the great losses to intelligent discourse when Playboy ceased publishing its flagship magazine. But with a half-century of history speaking with some of the most revered and notorious figures of the era, Audio Up will have no shortage of material. That history includes interviews with both Martin Luther King Jr. and the man who killed him, assassin James Earl Ray. Presidential candidate Jimmy Carter famously confessed to having lust in his heart, and the Interview chronicled many of the great film directors of the era at the height of their influence, including Francis Coppola, Federico Fellini and Martin Scorsese.

 “I had the opportunity to learn at Hef’s feet,” says Jellinek, from whom bringing the Interview back to life is a tribute and public service. “People don’t see this type of work. It’s a lost art. You get to be fly on the wall and be with amazing historical figures from the 20th century.”

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