a magazine that changed America.

- Playboy is the most famous media startup of the American century.

- [Narrator] Created in Chicago by Chicagoans.

- Here we were in this shop on the corner on North Michigan Avenue, but we were having an impact all over the world.

Clubs, casinos, TV shows.

- Good evening.

I'm Hugh Hefner, your host.

I'm glad you could join us.

- [Narrator] A celebrity-filled shrine to the sexual revolution.

- It was kind of like a pornographic Star Trek.

- [Photographer] Smile a little bit more.

- [Narrator] "Playboy" turned Chicago's reputation on its bunny ear.

- They had the beacon on top of the Playboy Building.

It was like a Batman signal.

You know, people would flock to it.

- And we would take our three-inch heels off and get on top of that piano and do our go-go dancing up there.

- [Narrator] Hugh Hefner battles feminists- - The day that you are willing to come out here with a cotton tail attached to your rear end.

(audience laughing and clapping) - [Narrator] The Chicago Archdiocese- - The Catholic Church described him as an agent of the devil.

- [Narrator] The mayor and law enforcement- - I'm Hugh Hefner.

Whack.

I mean, they really beat him up.

- [Narrator] And city prosecutors.

- Jim Thompson, who was busy putting scalps on his belt.

- It really was a Chicago story for me, and I started the magazine, you know, with a Chicago dream.

- [Narrator] "The Making of Playboy."

Next, on "Chicago Stories."

(pensive music) (train clanking) (pensive music ends) (lightheted music) (birds chirping) (Narrator) "Playboy" magazine sprang from the dreams of a boy raised on Chicago's Northwest Side, back when it was mostly prairie.

Though Hugh Hefner adored his childhood, he described a home stifled by repression.

- I think my home was classic Midwestern Methodist Puritan.

There was no drinking in my home, no swearing, and also no real show of affection or emotion of any kind in my home.

- [Narrator] Hefner claimed his mother wanted him to become a missionary, but he was cut from a different cloth.

- His mom said, "It was not a repressed household.

I can still see the pinholes in the wall.

He grew up dreaming of the Vargas Girl."

- [Narrator] Hefner's other obsession was movies playing for a quarter at the Montclare Theater.

- Of all the gin joints in all the towns in all the world, she walks into mine.

- That's where the heroes were.

That's where you had the stories of standing up for what was right.

That's where he got his sense of romance.

His favorite movie was "Casablanca."

- Now, now.

(romantic music) Here's looking at you, kid.

(soft music) - [Narrator] Skinny and shy, Hefner was not exactly leading man material at Steinmetz High School.

After a teenage crush spurned an invitation to a hayride, Hefner recast himself as a cool cat.

- I kind of reinvented myself and started referring to myself as Hef instead of Hugh.

And I changed my wardrobe.

I did a lot of other kinds of things to reinvent a sort of classic image of a high school student.

- [Narrator] The aspiring cartoonist documented every detail of his life.

- Well, I think that the last couple of years of high school were the high point for me in terms of creativity.

- [Narrator] Hefner made corporal in the Army during World War II, but hurried back to the Midwest when it ended.

He studied psychology and playwriting at the University of Illinois-Champaign on the G.I.

Bill and edited a campus humor magazine called "Shaft."

- [Hugh] I added a new feature called the Coed of the Month.

Fully clothed, but obviously the forerunner to the Playmate of the Month.

But at that point in my life, I was very anxious to get on to whatever my life was gonna be.

I wanted to get married and, you know, find the right job.

- [Narrator] Still a virgin at 22, Hefner set his heart on one particular co-ed named Mildred Williams.

- They were both very progressive.

They were both intellectually curious.

He had a wickedly smart sense of humor, actually something he and my mom shared.

- [Narrator] They were engaged, but Hefner's joy was cut short when Williams confessed to an affair.

He called it one of the most devastating moments of his life.

- I think that incident created a certain wariness about women.

- [Narrator] They went ahead with the wedding, had a daughter, and settled into an integrated neighborhood on Chicago's South Side.

- [Christie] They didn't have any money, but our apartment on the South Side was in a magazine feature.

You know, they had the classic Womb Chair, and my nursery was wallpapered with Pogo comic strips.

- [Narrator] Hefner slogged at several publishing jobs, writing promotional copy for "Esquire."

When the publisher moved the magazine to New York, the young man faced a crossroads.

- He tied his future to Chicago, to the Windy City.

- He wanted to be part of the skyline of Chicago.

He wanted to be in those lights up there.

- I started thinking very much about my life and the fact that I wanted to do something else.

And it was then that I really started thinking seriously about creating "Playboy."

And the notion of "Playboy" was quite frankly to simply create a lifestyle magazine for the young urban guy, for single guys, because all the men's magazines after World War II were outdoor adventure books.

And I felt there was room for a different kind of men's magazine.

So I went to everybody I could think of, friends, relatives, and got a few hundred dollars here, a few hundred dollars there, total of 8,000.

- [Narrator] "Playboy" would modernize "Esquire's" blend of fiction, journalism, and cartoons for a younger Midwestern audience.

A talented art director named Art Paul designed the now iconic bunny logo in just 30 minutes.

Hefner knew his magazine was still missing something, until he read about a calendar company on Chicago's West Side that held the rights to a set of nude prints featuring Marilyn Monroe.

Monroe had posed a few years earlier under a pseudonym, when she was a struggling actress, for just 50 bucks.

But her fortunes changed.

- Marilyn was the hottest new thing in Hollywood, and it came to light in all the PR around her that she had done these cheesecake calendar photos where, as she put it, she had nothing on but the radio.

- [Hugh] So I drove out in my beat-up Chevy and I had a very good day, and I walked out of there with the rights to reproduce the calendar picture for $500.

- He didn't know if it was gonna be a success or not.

And it sold 50,000 copies, which astounded him.

- Talk about a turnaround in your life from just feeling like completely, you know, what's the point, where am I going, to riding this rocket ship.

- [Narrator] The 50-cent magazine flew off shelves.

Monroe didn't earn another dime.

- Hefner never asked for permission.

Her career obviously was okay, but it was, in her mind, another invasion.

- [Narrator] In an era when even talking about sex was taboo, Hefner's timing was impeccable.

- It was such a conservative decade.

There was a tremendous amount of pressure to get women back in the home.

The women had been out in the workforce during World War II, and this was really a post-war phenomenon.

- It was a rebellion against the conformity of Eisenhower's America.

And it was sort of one of these historical situations where the right man with the right idea in the right setting all come together.

(soldiers cheering) - [Narrator] World War II veterans were familiar with pin-ups, but "Playboy" crafted a fantasy of alluring and attainable women.

- In fact, it was my mother who came up with the name Playmate.

The first idea was it was gonna be Sweetheart of the Month.

She had the idea that you're looking for someone you're gonna share your life with, a playmate, not a pin-up.

- [Narrator] Playmates were intended to reflect a wholesomeness that Hefner called "the girl next door."

He convinced a 20-year-old subscription manager with whom he was sleeping to pose topless, calling her Janet Pilgrim in a dig to his Puritan heritage.

- "Playboy" was getting subscriptions like wild based on her pictures.

All of the success that Playboy met was often not shared by the women who made that success.

- Those, you know, Playboy Playmates were one kind of woman, and that was what Hef liked.

And the fact that that became a kind of Barbie-style archetype for what American beauty is is a real shame.

- [Narrator] Playboy had quickly outgrown Hefner's apartment, moving operations across the street from Holy Name Cathedral.

He was respectful of the Church at first, pulling one issue from Chicago newsstands after complaints about a medieval tale featuring randy nuns.

- The Catholic Church, or figures in the Catholic Church, just utterly condemned "Playboy" and Hefner and described him as an agent of the devil.

- [Narrator] Newly elected Mayor Richard J. Daley was not a fan either.

- Daley comes in and kinda felt like everybody's father, and Hefner's role in this was to be that kind of crazy big brother who would, you know, buy you beer and hand it to you in the background.

He was that naughty part of Chicago, which has always been part of Chicago.

- [Narrator] Censorship battles arose from the very start.

The U.S. Post Office refused to grant Playboy a second-class mailing discount typically issued to magazines.

- Well, we had had problems with the government, including the Chicago government, from very early on.

I had to go to court to get a second-class mailing permit.

- [Narrator] Hefner sued the post office and won $100,000 in damages.

Circulation grew to a half million magazines a month, and the nation took note of the young Chicago rebel.

- [Mike Wallace] Hugh, we checked this month's issue and found 20 pictures of girls in various stages of undress.

Isn't that really what you're selling, kind of a high-class dirty book?

- No, I don't think so at all.

There's an important distinction here.

Sex always will be an important part of the book because sex is probably the single thing that men are most interested in.

- Chicagoans have always had a knack for knowing what people wanted.

The thing that Hef knew America wanted was sex.

There's a sense sometimes that Hugh Hefner invented sex or something, and he didn't, he just unleashed it.

He's also objectifying the next-door neighbor and the shop girl and the teacher and sort of turning them into sexual objects.

You know, for Hef, sexual liberation is for men.

- [Narrator] While many saw "Playboy" as nothing more than a skin magazine, Hefner wanted more, (bright music) to show young men how to enjoy a sophisticated lifestyle.

Hefner empowered a ragtag team of Midwestern creatives who were short on editorial experience but not on talent and ideas.

- I always have felt that I could not have started "Playboy" in New York and probably in Los Angeles, that what was unique about Chicago is the fact that there was a great deal of talent here that was not being utilized.

(air whooshes) - The magazine attracted geniuses.

(air whooshing) - [Janice] Art Paul, LeRoy Neiman, Shel Silverstein.

- [Narrator] These local artists set off a different kind of revolution inside "Playboy's" pages, breaking down the barriers between commercial and fine art and forging a distinctive Chicago look.

- Every month, you could sit and look at that magazine, and if you didn't stop on the cartoons and go, "Oh my God, that's so brilliant."

- [James] We were the heart of the country.

That distance meant everything.

- [Narrator] Hefner made one concession to the East Coast establishment, hiring a New Yorker named A.C. Spectorsky as associate publisher.

Spectorsky's connections and Hefner's wallet turned "Playboy" into a showcase for acclaimed authors like John Steinbeck, Jack Kerouac, and Ray Bradbury.

- You know, Playboy pried opened the safety deposit box that was New York City with a big, giant screwdriver called money.

- [Narrator] Playboy was booming.

But as Hefner's star rose, his family splintered.

He left his wife and two children.

- I came out from behind the desk and started living out the life.

And I literally reinvented myself in that timeframe, in the space of just a few months, in pretty much the same kinda way that I did when I was in high school.

I became Mr. Playboy.

(light jazz music) - [Narrator] Capitalizing on the magazine's success, Hefner launched a variety show called "Playboy's Penthouse."

- Hello there, glad you could join us this evening.

I'm Hugh Hefner, editor-publisher of "Playboy" magazine and your host, and this is "Playboy's Penthouse."

Come on in and meet some of our guests.

Well, here we have Eleanor Bradley and Miss Joyce Nizzari, two of our most popular Playmates, and Lenny Bruce.

- Lenny Bruce was, like, sneaking up on us or popping open a bottle of champagne.

(bottle pops) - Oh!

(laughs) Isn't that sick?

(people laughing) Oh, boy, the champagne is really making my nose bubbly!

(people laughing) - [Joyce] It was very exciting.

- He obviously was not trained as an actor, and he didn't know what to do with his hands as the host of the show.

And I don't know who, but somebody said, "What if you had a pipe?"

You know, it's the classic give-the-actor-a-prop.

That's how and why he started smoking the pipe.

So it was kind of creating a persona.

(soft jazz music) ♪ They're writing songs of love ♪ ♪ But not for me ♪ - [Narrator] At a time when Black performers had few television opportunities, Hefner put artists like Ella Fitzgerald and Sammy Davis Jr. front and center.

♪ Give me the Playboy in Chicago ♪ ♪ Man, this is my hometown ♪ - [Narrator] Sparking controversy by mixing Black and White guests.

- The syndicator went back to Hef to say, "We can't get carriage in the South because it's integrated, so we need to change that."

And my father's attitude was, well, then we're not gonna get carriage in any stations in the South.

(upbeat jazz music) - [Narrator] Hefner's battles in the Jim Crow South were expected, but he was infuriated by hometown resistance, something that came to a head in 1959.

- Jazz was really, really big at that time, and Chicago was just full of it.

I mean, it was just so much fun.

And Hugh Hefner started having the Playboy Jazz Festivals.

That was the talk of the town.

(energetic jazz music) - [Narrator] Count Basie and other luminaries were scheduled to play at Soldier Field until Catholic leaders pressured Mayor Daley.

- So they pulled the permissions at Soldier Field more or less at the last minute.

- [Narrator] Hefner moved Jazz Fest to Chicago Stadium and donated the first day's receipts to the Urban League, where Gloria Johnson worked as a secretary dreaming about the after-parties.

- All I can think about, how can I get myself an invitation to that party?

I picked up the phone and called Hugh Hefner.

I said, "Mr. Hefner, my name is Gloria Johnson.

I am 19 years old.

I measure 34, 22, 34 with the complexion of a Boston coffee, and I'd like to come to your party."

He said, "Gloria, I'll make sure that there's an invitation waiting for you at the door."

I had my little, what, little gold lame dress on, went into the main ballroom, looked down upon a whirling sea of dancing celebrities.

All of a sudden, a warm, reassuring hand reached out to me and said, "I'm Hugh Hefner.

May I have this dance?"

(gentle music) I felt like Cinderella.

(car revving) - [Narrator] All of Hefner's own dreams were coming true.

The boy whose mother wanted him to become a missionary had turned into a messenger of pleasure and consumerism.

But Hefner's leading ladies were never allowed to upstage him.

- I thought that there weren't other females in his life.

I was very young and innocent, but found out that that wasn't so with him.

I started dating other men, and when he found out about it, he acted as if it was the most heartbreaking thing that had ever happened to him.

- So for all of this talk about freedom and liberation, it really did not extend to his personal relationships almost at all.

When it came to the women in his life, he was incredibly controlling.

- [Narrator] Nor did there seem to be any place for family, faith, or commitment in Hefner's world.

- [Hugh] I was married once.

It was not, I must say, a very happy experience for me.

- [Narrator] Hefner finalized his divorce in 1959.

- I had very little time with my father growing up.

I would describe it best as the relationship that someone might have with, like, a favorite uncle.

So, I knew he loved me, I knew he would always be there if something happened.

He had no idea who my friends were.

He didn't know what I was interested in in school.

We saw each other, like, three or four times a year.

I mean, that's it.

- [Hugh] I am very, very selfish, I'm very self-oriented, and I think that everybody should be.

Intelligent self-interest is for the good of everyone.

The person who spends all of their time thinking about others accomplishes almost nothing.

(upbeat music) - [Narrator] As "Playboy" magazine greeted a new decade in business with one million subscribers, seismic shifts rocked America for men and women.

The Food and Drug Administration approved the first oral contraceptive.

- It's an age of vigor and vitality.

Or as Kennedy would've said, "Vig-uh."

- [Narrator] Hefner had donated to John F. Kennedy's campaign and celebrated the president's inauguration in Washington.

- It really kinda shoves in the background the old Eisenhower norms.

Hefner is right in the middle of all of that.

- [Narrator] Hefner brought the magazine to life in 1960, launching a swanky lounge that required a membership key called the Playboy Club.

But the city tried to stop him yet again.

- When we opened the first Playboy Club in February of 1960, the city of Chicago didn't wanna give us a license.

We had to go to court to get that.

They objected to the Bunny, and they objected, first and foremost, I think, simply to the concept of Playboy.

(lively music) - [Narrator] Hefner won that round too.

The Playboy Club was an instant success and expanded quickly to other cities.

- I loved meeting people when they came in and seeing where they're from, what they came there for.

- [Narrator] Bunnies, fitted in satin corsets and cotton tails, served cocktails in four different rooms.

Marli Renfro made her way to Chicago after playing Janet Leigh's body double in "Psycho."

(suspenseful music) (Marion screaming) She posed for "Playboy" and found work at the new club.

- You go to any bar in town and a mixed drink was 35 cents.

The Playboy Club charged $1.50.

Nobody complained.

- It was a great place to entertain.

Somebody coming in from out of town, they loved it.

There's always that prospect, wow, what might happen if I go there?

- [Narrator] Playboy integrated its clubs, boosting the careers of comedian Dick Gregory and other African American performers.

Gloria Johnson was looking for a change when she was invited to become the first Black Bunny, three years before the Civil Rights Act banned workplace discrimination.

- The biggest room was the living room.

We would take our three-inch heels off and get on top of that piano and do our go-go, do our dancing up there, you know?

- [Narrator] Hefner's brother, Keith, developed a 44-page Bunny manual.

It included demerits for chewing gum or donning a scruffy tail.

- There was like a million things you had to remember for drink orders, and I had a (laughs), I had a bad memory, so that didn't work for me.

But, you know, they would teach you things like the Bunny Dip.

- If you go down, arch your back like that.

It brings you much closer to the table.

- Well, the Bunny Dip is the way you serve a drink.

You know, you wouldn't wanna, like, bend over, right, with the way we were dressed in our little costumes.

We had to be ladylike, so we had a certain posture.

It was a job that required a dedication and hard work.

- [Narrator] The manual forbid Bunnies from dating customers, unless they were VIPs.

- So he hired, (chuckles) this private detective agency called Willmark, and they would come in and they would actually hit on the girls, you know, just to make sure that the girls were not dating the members.

(playful music) It's so funny because people would say, "Oh God, Willmark is in the house, girls, Willmark is in the house."

(laughs) - [Narrator] Someone else was posing undercover at New York City's Playboy Club.

Feminist icon Gloria Steinem made her mark as a young journalist when she worked as a Bunny for a 1963 magazine expose.

Steinem described a sexist environment that exploited and demeaned women.

She wrote about toiling for long hours at minimum wage, constant propositions, and mandatory venereal disease exams.

- So, Hefner wrote her a letter after the article came out saying, "Okay, I'm taking that out of the requirements for the Bunnies."

Steinem's article actually had a huge effect.

- [Narrator] For Johnson, the job was well worth it.

She relished the opportunity to earn good money for the first time in her life and make lasting connections.

- Playboy represented family to me.

It was the closest thing that I had ever felt to ever really belonging to anything.

- [Narrator] Lines stretched down Michigan Avenue even when temperatures sank below zero.

There were 50,000 members by the end of the first year, making it America's hottest nightclub.

Al Capone was no longer Chicago's most famous renegade.

- And Chicago became Playboy.

Big time!

- [Narrator] Hefner heightened the mystique when he opened the Playboy Mansion just blocks away in the Gold Coast.

A brass plaque at the front gate bore a Latin inscription that said it all.

- "If you don't swing, don't ring."

The butler opens the door and then you go in around the corner and you're in the main ballroom.

It was like I was in a castle of a king.

There was a Picasso above the fireplace.

- [Narrator] Hefner outfitted the mansion with hidden passages, cutting-edge electronics and other toys, including a bowling alley, and a game room where he played pinball, Monopoly, and foosball all night long.

(Hugh yells) - Oh!

(people clapping) Fantastic!

- You'd slide down a fireman's pole in the living room to get to the underground pool.

And then there was a big window where guests at a bar could watch the swimmers in the pool while they had cocktails.

(laughs) It was unbelievable.

(dog panting) - There's a picture of Christa Speck jumping into the pool topless.

That was like 1/250 of a second.

And everyone who saw "Playboy" in the 60s remembers that image.

- I remember taking my mom there, and she did say, "That's a funny place to put a mirror."

My mom was so naive.

(laughs) (light music) - [Narrator] Chefs offered 24-hour room service to guests and the two-dozen Bunnies who bunked at the mansion.

- A lot of the girls worked late.

At like three o'clock in the morning, you can come and order lobster from the kitchen and, I mean, anything your heart desired.

(chuckles) He was a good host.

- [Narrator] Hefner could have eaten lobster and caviar every night, but never outgrew his mother's recipes.

- Hefner.

I wonder if we could get something to eat.

- Pot roast and meatloaf.

- Maybe a couple of ham sandwiches.

- (laughs) He had really down-to-earth tastes.

- [Narrator] Hefner was often compared to F. Scott Fitzgerald's protagonist Jay Gatsby, opening his mansion to everyone from Barbra Streisand to Tony Curtis.

- He had the Rolling Stones there that stayed and trashed a couple of rooms and then weren't invited back again.

Those guys, I'm telling you.

- [Narrator] The editor worked around the clock in a customized bed, a homebody who blurred the distinction between work and play.

- He had a very distinct look, obviously.

Early on, decided particularly 'cause he was working around the clock that he was gonna just stay in pajamas and a robe unless he was going out, and so that became his look.

(soft music) - [Narrator] Fueled by two-dozen Pepsi-Colas a day and the stimulant Dexedrine, Hefner shuttered his bedroom and bent the clock to his needs.

- [Hugh] I have created my own world with my own set of values rather than accepting those that had been there before me.

- She's the same girl that was in the one I did in the background.

- Could be.

- [Narrator] Hefner's one true love was his magazine.

He was a perfectionist who demanded the very best.

- [James] He paid attention to every square inch of the magazine.

- [Hugh] It's the journal in the profile or- - Is this good enough?

Have we done enough research?

Can this be better?

- Memo to the head of our promotion art department or whoever is handling- - [James] I got a 65-page single-spaced memo spoken into a Dictaphone.

- [Hugh] I particularly like the shots of the man.

- I promised myself that someday I will read that memo.

(typewriter clacking) - [Narrator] Hefner spent years grinding out 25 installments of "The Playboy Philosophy," arguing for women's access to birth control and abortion and repeal of 19th century sex laws like sodomy.

- One of the purposes of that was to change the laws.

And by God, he did it over time.

I mean, I'm not saying he's solely responsible, but somebody had to start that ball rolling, and I think that ball was started by Hugh Hefner.

- [Narrator] Letters poured in from readers, leading Hefner to create the Playboy Forum and the Playboy Foundation to support First Amendment rights.

He championed Lenny Bruce after he was arrested for obscenity at the Gate of Horn nightclub, (camera shutter clicking) one of many trials the boundary-pushing comedian faced.

- He stayed at the Chicago mansion, and Playboy's lawyer would give him a fresh shirt to wear to trial every day.

- [Narrator] An ambitious Cook County state's attorney won a conviction against Bruce.

His name was James Thompson.

- Chicago was a Catholic town, and Catholic politicians and Catholic churchgoers did not like Mr. Hefner or his magazine.

- [Narrator] Four vice squad officers yanked Hefner out of bed (camera shutter clicks) and arraigned him seven months later over a Jayne Mansfield pictorial.

- So they turned around and arrested me, and I was put on trial for obscenity for some pictures on Jayne Mansfield.

But the real cause behind it was the criticism we'd made of the government for Lenny Bruce.

- [Narrator] The obscenity case ended in a hung jury and Hefner walked, for the time being.

- Hefner was very aware of if you brush them the wrong way, they would come after you.

- [Narrator] And yet, it seemed nothing could stop Playboy's march to the top.

Hefner leased office space in the Palmolive Building in 1965, the culmination of a longstanding dream.

Its beacon had captivated him as a boy.

Now the 40-year-old publisher installed nine-foot-tall block letters and rechristened it the Playboy Building.

Hefner had truly arrived.

- Driving to work every day along Lake Shore Drive, an exquisite drive, and seeing the Playboy Building was a thrill.

I would get goosebumps to think that I was gonna walk into those offices.

- [Narrator] Hefner got the headlines while his staff sweated the details just as feverishly, transforming "Playboy" from a guilty pleasure into a first-rate magazine.

- "Playboy" was in many ways a great work of craftsmanship.

He cut no corners, spared no expense.

The magazine itself physically was the best quality photography and printing that you could get at the time.

Everything about that place was first-class.

(lively music) - [Narrator] The Playboy Interview remade the genre and sparked controversy with in-depth profiles of Malcolm X, Fidel Castro, and neo-Nazi George Lincoln Rockwell.

Ann Landers' advice column in the "Chicago Sun-Times" inspired the Playboy Advisor.

- Playboy was getting a thousand letters a month.

It could be hilarious, heartbreaking, hopeful.

A reader wrote, "Dear Playboy Advisor, I masturbate with sandpaper.

Do I have a problem?"

And I said, "Yes, but not for long."

- And it became kind of a joke in a way out in the world where people said, "It's great writers and people with no clothes on."

And of course I found that to be, in a way, totally charming.

- [Hugh] Let's set me up on a flight with them, too, on Thursday morning.

- [Narrator] Though women had been typically relegated to secretarial and other supporting roles at Playboy and most organizations at the time, some, like chief copy editor Arlene Bouras, began rising at Playboy.

- It was not only a men's magazine, it was a man's world, but there were a lot of powerful, wonderful, talented women in it.

- [Narrator] Bobbie Arnstein, a pint-sized powerhouse with a wicked sense of humor, rose from receptionist to Hefner's executive assistant.

She played a more crucial role than her title suggested.

- She was a lovely person, a really smart person, devoted to Hefner.

Bobbie was his Jiminy Cricket sitting on his shoulder.

She kind of ran the Hugh Hefner machine.

- [Narrator] 19-year-old Janice Moses had failed to land a job after 30 interviews when Playboy offered her a lifeline.

She rose from stylist to photo editor, producing hundreds of shoots.

- Art Paul would hand me drawings of ideas that he had that I had to turn into props or wardrobe or something for the covers, because, you know, the covers always had a Playboy Bunny hidden somewhere in them.

And if I wasn't doing that, I was building Playmate sets.

We spent an enormous amount of time building that set, crafting that lighting, doing their hair and makeup, choosing the wardrobe, as minimal as sometimes it seemed.

- Okay, we're ready, shooting now.

- Okay.

- Getting ready.

Right there.

- If I wanted to work hard and make a contribution, I was listened to.

- Did we have a makeup man on this?

- No.

- She looks really good.

Look, I love her smile.

She has the greatest natural smile.

- [Narrator] While the photo department agonized over 8x10 transparencies on the 11th floor, the editorial staff spent months developing a single article in a setting one floor down that was no less erotic.

- There were wooden elevator doors that were carved with nudes.

You go to the 10th floor and get off and there would be an Italian marble desk the size of an aircraft carrier, and behind it, the most beautiful woman you'd ever seen in your life.

And it was kind of like a pornographic Star Trek.

It was just out of this world.

- [Narrator] The sexual revolution spread across America in the late 1960s, not just in Playboy's hallways.

Whether the magazine anticipated, triggered, or simply reflected the time is up for debate.

- The revolution wasn't just created by women without their clothes on.

Let's face it, the revolution was created because you had a magazine full of ideas and it was coming out of Chicago.

- We were hot stuff, you know?

Imagine your circulation goes one, two, three, four, five million.

They're opening clubs all over the country, all over the world.

It's as if we could do nothing wrong.

(thunder booming) - Mayor Daley and the Catholic Church looked on warily as the Playboy empire flexed.

- I think it was love-hate, really.

And I don't think that there were too many people either in politics or in the social life of the city who found Playboy an enhancement necessarily.

They were happy to have the revenue.

- [Narrator] The Prince of Pleasure spent lavishly on his trappings, including a $4.5 million DC9 dubbed the Big Bunny.

(upbeat music) Hefner took another stab at TV in 1968, filming a variety show in Hollywood.

(light music) - Good evening, I'm Hugh Hefner, your host.

I'm glad you could join us.

It's going to be a fun evening, I think.

A lot of friends are here.

We're glad you are too.

I was just talking to Johnny Mathis.

- [Narrator] The series lasted only two seasons, but a chance encounter with an extra would redirect the Midwesterner's life.

(upbeat music) ♪ In-a-gadda-da-vida, honey ♪ ♪ Don't you know that I'm lovin' you ♪ - And Hefner said he nearly fell out of his chair when he sees her dancing.

- [Narrator] Barbara Klein recalls their meeting somewhat differently.

- He approached me that day while I was sitting, reading my book, and he asked me out.

The first time Hef asked me out, I said, "I've never dated anyone over 24."

And he said, "Neither have I."

(people laughing) He was 42 at the time.

- [Narrator] Hefner was smitten by the 18-year-old UCLA co-ed.

He suggested changing her name to one better suited to a theater marquee: Barbi Benton.

- Tell me, whose idea was this nine-page pictorial?

- Well, he suggested it, and I just decided that I should do it.

I don't find anything wrong with nudity if it's done in good taste.

I'm glad I did it.

I think that it opened some doors.

It may have closed as many doors as it opened though.

(cars honking) (tense music) - [Narrator] Benton got a glimpse into Hefner's tense relationship with his hometown during the 1968 Democratic Convention when the publisher and some friends observed Vietnam War protests in Lincoln Park.

- When these police asked Hef what he was doing in the neighborhood, he said, "I live here.

I'm Hugh Hefner."

Whack.

(chuckles) "Sure, you're Hugh Hefner."

Whack, whack.

I mean, they really beat him up.

He wouldn't go to the police because he said, "What are they gonna do?"

It's a very bad scene in Chicago and one man was in control.

(protestors yelling) (tense music) (plane engine humming) - [Narrator] As Hefner's ties to Chicago frayed, Benton and Hollywood pulled him west.

(plane whooshing) - I found a gate in Holmby Hills that had a padlock on it.

I pulled over and hopped that fence, crossed my fingers that there weren't any Doberman Pinschers.

To my surprise, I saw the most beautiful house in LA.

- [Narrator] Hefner paid $1 million and transformed the mock Tudor estate into his private Shangri-La.

- [Barbi] He loved the weather, and he liked being able to sit outside at the mansion and play backgammon on the lawn, and lots of monkeys.

- Now, the water here is all heated to about 82 degrees.

It turns out that this proved to be, for some reason, the most popular spot of all.

Has something to do, I think, with the emphasis that everybody's putting on health these days, I think that's probably what it is.

- I think that was sort of the beginning of the end for his stint in Chicago because you see him slowly but surely gravitating toward the Playboy Mansion West.

- I'm enjoying the outdoor part of this thing, I think, more than the indoor, and I've always been an indoor guy.

(upbeat music) - [Narrator] In the early 1970s, "Playboy's" circulation peaked at 7 million monthly readers, making it the world's largest-selling men's lifestyle magazine.

Playboy Enterprises went public.

Its empire consisted of 17 clubs, three casinos, four resorts, two movie theaters, a record company, book and film divisions, modeling, and limo agencies.

- It was watching everything we did turn to gold.

The red carpet rolled out every time you made a phone call, and it was all coming out of the imagination of Hef and the team he'd assembled in Chicago.

- [Narrator] But on streets across the city, nation, and world, America was at war.

(people yelling) (rocket booming) Soon Hefner and Playboy would be too.

- [Astronaut] Okay, Houston, we've had a problem here.

- Join us!

Women!

Join us!

- [Narrator] The trouble started after Hefner commissioned an article about the women's liberation movement.

It focused on some of the more radical feminist groups, describing them as "militant man-haters."

- Morton Hunt was writing about women in the women's movement in kind of a snotty, divisive way, that instead of fixing the feelings of women who were annoyed by Playboy, it exacerbated it.

- This inhuman system of exploitation will change, but only if we force it to change.

- [Narrator] Playboy went into damage control after an internal memo was leaked, in which Hefner wrote, "These chicks are our natural enemy.

It is time to do battle with them."

- These women were really tough, and they were mad.

They were really mad.

- There are a lot of women in this country who feel that they're being pushed around.

- [Narrator] Something Hefner found out when confronted by feminist author Susan Brownmiller on "The Dick Cavett Show."

(audience clapping) - [Dick] What do you think men are doing wrong?

- They're in charge.

- (chuckles) Yeah.

- Yeah.

And they oppress us as women.

They won't let us be.

And Hugh Hefner is my enemy.

- [Dick] Oh, is Hef your enemy?

We really set you up tonight, didn't we?

(audience clapping) - [Susan] Hefner has built an empire based on oppressing women.

(audience clapping) - I'm more in sympathy than perhaps, you know, the girls realize with- - Women, women.

- Women.

- I'm sorry.

- Yes, I'm 35.

- Than the ladies realize.

I've used girls referring to women of all ages.

- You should stop.

- Yeah.

If you wanna be called a boy- - Would you like- - [Hugh] Oh, I see, okay.

(chuckles) Um.

(audience laughing and clapping) - How could you be so shortsighted that you would go to have a serious debate on "The Dick Cavett Show" about the feminist movement and be calling women "girls"?

She did get most of the applause on the show, and the audience seemed to find him to be a bit of a buffoon.

- The role that you have selected for women is degrading to women because you choose to see women as sex objects, not as full human beings.

- What might be seen as- - Hold on now.

The day that you- - Yeah!

(audience clapping) - That I be degrading- - I wanna say, I haven't finished.

The day that you are willing to come out here with a cotton tail attached to your rear end.

(audience clapping and laughing) - He had a very strict idea of what women should be, whether they were the women in his life or the women in his pages.

And I don't agree with the idea that sexuality has to look like a thin, White, blonde woman in her early to mid-20s in order to be valid.

- [Narrator] While feminists argued Hefner exploited women's bodies, a new competitor revealed even more of them.

"Penthouse" magazine's American debut sparked an existential crisis at Playboy called the Pubic Wars.

- Hefner dug in his heels when it came to publishing full frontal nudity.

He did not want to do it because he thought it cheapened "Playboy."

- Well, then along comes "Penthouse."

Before too long, we imitated it too.

You know, the line had been moved.

- [Narrator] The line never bothered Candace Collins, a Bunny, Playmate, and nine-time cover girl.

- I might still be living in Dupo, Illinois, if I hadn't, you know, signed up with Playboy.

I'm from a town of 3000 people, you know, it's a railroad town on the banks of the Mississippi.

I felt empowered by being a Playmate.

- I think that Hefner had this knack for looking at women who were from tougher circumstances or who didn't have financial prospects in other ways and exploiting that need.

(protestors yelling) - [Narrator] Attacked by feminists on the left, the government on the right, and competitors in the middle, Hefner retreated every other week to his West Coast mansion.

- I think Hefner was always destined for L.A. Hefner was kind of seduced by stardom in the same way that people were seduced by his stardom.

I think he believed that Chicago was small-town America, and in a way it is.

I mean, it's a big city with a small-town heart.

Playboy, I think, had a romance with Chicago, and I don't honestly know if Chicago had a reciprocal romance with Playboy.

(soft music) - [Narrator] Hefner's ties to Chicago unraveled in March 1974.

Agents from the Drug Enforcement Agency arrested Bobbie Arnstein in front of the mansion with a cocaine vial in her purse.

Hefner's beloved secretary was already emotionally fragile and now stood accused of helping a boyfriend transport a half pound of cocaine from Florida to Chicago.

- They were all convinced that Hugh Hefner and the Playboy Mansion was somehow a center of drug use and drug distribution.

- [Narrator] The U.S. attorney for the Northern District of Illinois was the same prosecutor who had tried Lenny Bruce a decade earlier: James Thompson.

- Big Jim Thompson did not like Mr. Hefner and went after him.

- Hef did not do cocaine while I was with him.

He did not want to do drugs, other than the Dexedrine to stay awake and marijuana.

- [Narrator] Prosecutors leaned on the testimony of a convicted drug dealer who had changed his story about Arnstein's involvement in Miami.

(soft music) Arnstein was convicted of conspiracy to distribute cocaine and sentenced to 15 years in prison.

- [Lawyer] I don't think you ought to give any statement at all.

- Well, I think it's absurd.

- [Lawyer] Don't think you ought to give any statement.

- My lawyer suggests that I not give any statements.

It's not my personal feeling.

- Okay.

- You're welcome, sorry.

- Hef blamed the government.

He said, "They're relentless.

They're after me, and they're using her as a pawn."

- [Narrator] Though Arnstein's lawyers explained she would likely get a reduced sentence, perhaps even probation, she sank deeper into depression and drug use.

- Not too long after that, went to a local hotel on Rush Street and committed suicide.

(soft music) - [Narrator] Arnstein's suicide gutted Hefner.

He flew back to Chicago for a hastily called press conference.

- She was one of the best, brightest, (melancholy music) most worthwhile women I have ever known.

She will be missed.

- [Narrator] Hefner served as a pallbearer at Arnstein's funeral, the first he had ever attended.

- It just devastated my father that she'd been driven to this by, and I will say it, by Jim Thompson, who was busy putting scalps on his belt for his own political aspirations.

- [Narrator] The prosecutor denied targeting Hefner.

"I have no quarrel with him, his philosophy, or his magazine."

The Justice Department dropped its case against Hefner 11 months later.

Thompson was elected governor the next year, winning the first of four terms.

- A classic corrupt Chicago political moment.

It crossed a line, it took a life, and he left.

- [Narrator] Hefner's nine-year romance with Benton also faded out - For Hef, it was an eternity.

He just didn't behave himself.

I was smart enough to leave Hef.

I don't know why I didn't leave him sooner, but we always had a good time.

- [Narrator] Though the white-hot center of the Playboy universe gravitated west, the beacon over its Michigan Avenue headquarters never dimmed.

- We were producing a magazine out of that building with the same gusto the day before he moved as the day after he moved.

There was Hef, but the force of the magazine was in Chicago.

- [Narrator] And it was in Chicago where another Hefner, straight out of central casting, began her rise.

- Have you been comfortable with the way the magazine has treated women over the years in its presentation of women?

- Pretty much so.

I think you have to start from the underlying assumption of the magazine, which is it's for men and not for women, and therefore- - When I saw the way she could speak to people who I didn't ever think he was comfortable speaking to, you know, the kind of people who make the machinery of this empire work, I knew she could do that.

- [Narrator] As Christie ascended to president and CEO of Playboy Enterprises, her relationship with her father deepened.

- It was really gratifying for me to see how much he respected me, how proud he was of me.

He got a huge kick out of the fact that I was working in the company.

- Well, I am much blessed, and, you know, at the top of the list of many things I would have to rate my daughter.

- [Narrator] Hefner hunkered down in his West Coast mansion, weathering good years and bad, marriages, divorces, and scandals, including disturbing allegations of abuse and sexual misconduct.

(soft music) - Come in.

- Hefner remained sentimental about Chicago, (people chattering) though weary of the politics that hastened his exit.

- [Christie] He came back more than once.

- I have to tell ya, these were the best years of my life.

(crowd cheering) - He went back to Steinmetz to speak to the students.

- I think that this particular period of adolescence and growing into young adulthood is what it's all about because that's really the beginnings of everything.

All right.

- You know, for all the conflict that he had in Chicago, you know, with the Catholic Church, with the Daley machine, I think he remained incredibly fond of Chicago.

- [Bruce] I asked Hefner what this trip home had meant to him.

- Magic.

You can go home again.

- [Narrator] Hefner died from cardiac arrest in 2017.

He was 91 years old, and his complicated legacy continues to stir debate.

His presence has faded in the city where he became one of the 20th century's most influential magazine editors.

The mansion was carved up into luxury apartments, and the site of the first Playboy Club is now a parking garage.

The magazine ceased publishing a U.S. print edition in 2020, but the bunny ears are still recognized around the world, and no other Chicagoan made a bigger global impact, for better or worse, than Hef.

- As Hef once famously said, "It's like a Rorschach test."

You know, there are people who read it and find it really threatening and offensive, and there are people who read it and love it.

It's the same magazine.

- [Narrator] Hefner was buried in Los Angeles next to the screen siren who made all his dreams come true.

- It really was a Chicago story for me.

I, you know, I love this town, my dreams came from here, and I started the magazine, you know, with a Chicago dream.

(soft music) (soft music ends) (pensive music) (bright music)