The Hollywood mogul, his gay lovers — and his fashion icon wife

“Yeah, a little bit,” he says modestly. “A little bit.”

Yet all anyone wants to talk about is his sex life. And, in fairness, he has brought it on himself.

Diller and Warren Beatty, Washington, 1978

GETTY IMAGES

For much of his life, and although he never talked about it publicly, it was generally understood that Diller was gay. At the same time, however, he is married to Diane von Furstenberg, the fabulously glamorous force of nature who is best known as the creator of the wrap dress. When they got hitched, a reporter asked them if theirs was a platonic relationship: an odd question for newlyweds, but it captured the public confusion. “It’s very intimate,” von Furstenberg replied. Diller never spoke about it, until now.

He has just published a memoir, Who Knew. It tells of moguls and movie stars and how he changed American television. But he also writes about being gay and afraid that people would find out. Then, in what has been treated as a second revelation, he describes his relationship with von Furstenberg, the sparks of his desire for her. It is perhaps the first time that a man has caused a sensation by disclosing that he has sex with his wife.

When she first stayed the night at his place, even his butler was startled. The butler was a British fellow named Derek and, presumably by professional calling, he was generally as steady as a cetacean in an ocean swell, but apparently the sight of von Furstenberg coming down the stairs was too much for him.

“Madam,” he said. “May I ask you, did you sleep with Mr Diller last night?”

“Yes,” she replied. “I did.”

Hanging out by the pool that day with the film producer David Geffen and other friends, they had to hurry off to a guesthouse due to a sudden “explosion of passion”. Geffen walked in on them. “I caught a glimpse of David’s more than astonished face as he quickly closed the door,” Diller writes. “And, yes, I also liked guys, but that was not a conflict with my love for Diane. I can’t explain it to myself or to the world.”

But that does not mean the world is not going to ask. Perhaps people still struggle with the idea of sexual fluidity when it comes to media tycoons in their ninth decade, I tell him. Perhaps if you were 32 and running a crypto start-up, people would say, of course, why not.

“Yeah,” he says. “My wife, who’s a European — and all Europeans understand fluidity far better than American provincials — she just gets a laugh out of all this,” he says. “And I laugh at it because I think, you know, I’m not…” — he struggles for a way to put it — “I’m not in the trade any more.”

Do you mean you’re not dating?

“Yes. I’m not dating. That would be the word. So who cares? I’m hardly, you know…” It sounds as if he is about to say “a spring chicken”. He rests his head on one hand.

‘People speculate about what seems so natural to us’

I met his wife, as it happens, ten years ago, at the top of her own Manhattan building a few blocks from Diller HQ. She told me she slept there each weeknight in a glass penthouse: her bed looking out across a wild grass rooftop towards the Empire State Building. She said Diller tended to stay during the week at his own apartment in the Carlyle hotel. She was almost overpoweringly charming and she described their relationship just as he does. But I can see why people would be curious. I was too.

“I don’t know,” Diller says. “I mean, we’re both,” he pauses, “characters of some kind. I guess there’s some, like, interest or mystery and all that. And so I think people speculate… about what seems so natural to us. There’s always been speculation, scepticism.”

Diller at the beach with Calvin Klein and, right, the photographer Douglas Cloutier

COURTESY OF BARRY DILLER

I ask if he heard Andy Warhol’s observation: “I guess the reason Diller and Diane are a couple is because she gives him straightness and he gives her powerfulness.”

Apparently he has not, for he sighs and his face darkens. “Yeah, sure, she gets power,” he says ruminatively, his voice a rumble. “I mean, when Diane and I met, she was far more powerful than I was. She was selling 25,000 dresses a week. I was a failure at Paramount. I was soon to be thrown out.”

He was not thrown out; he turned the studio around. And now, of course, he is a billionaire and 83 and he can do what he likes. Except that he must submit to interviews like this one. His publishers at Simon & Schuster planned weeks of them. “I said, ‘You must be out of your f***ing minds. I’m not doing this,’ ” he says. “They said, ‘Well, this is what authors do.’ ”

Somehow Diller, who used to sit atop a corporation that owned Simon & Schuster, was not expecting it. He had not asked for an advance. “I want to be respectful and all that,” he says. “But I’m not out there hawking the book. And they said, ‘Well, you have to do this.’ ”

‘I wrote it, but why do I have to be interrogated about it?’

The first interview was for a Sunday breakfast show. “This journalist, whom I’ve never met and didn’t know, starts off with every personal question,” he says. “I’m like a deer [in the headlights], thinking, well, I could do that thing where you take off the mic and storm out.”

He managed to stay the course but, “I just felt, ‘What the f***? Why did I do this?’ ” he says. “I wrote it, so it’s not like I’m against any of it being read or revealed. But why do I have to be interrogated about it?”

He started cancelling interviews “as much as I could”, he says. But he has not cancelled me. I arrive at Diller towers on a humid afternoon. Diller asked the architect Frank Gehry for a tower block that looked like a ship’s sails. It has rippling glass walls banded with white horizontal stripes that fade from translucent to clear and back again. The downstairs lobby is vast and so minimally furnished that I hesitate at the doors, thinking it is still a building site, until I spot a desk at one end of it, manned by two guys in suits. A journalist I know at one of Diller’s companies steps from one of the lifts and asks, as he passes, who I am there to see.

“Jesus!” he exclaims when I tell him. He turns to the guys at the desk. “If we never see this man again, we’ll know what happened.”

On the sixth floor, a lady offers me a drink and then ushers me into the conference room. It is vaguely nautical too. There’s an oval table lined with legal pads and pots of large black pencils. The room is all angles and arcs, separated from the rest of the floor by a curving wooden screen. Diller steps out from behind the screen, dressed like a ninja in black slacks and a loose black silk shirt.

He is tall and broad and he has a large and rather heroic face: handsome and weatherbeaten, with a big, half-squashed nose and milky brown eyes. Several buttons of his shirt are breezily undone and his neck and the top of his chest are brown and riven with lines, like cracked sedimentary rock at the base of a cliff. He reaches for a remote on the table and pushes a button. Blinds slide down the curving floor-to-ceiling windows.

I tell him what the journalist said downstairs, about me never being seen again.

Diller and von Furstenberg at a premiere party for the Alfred Hitchcock film Family Plot, 1976

GETTY IMAGES

He puzzles over this for a moment. “Me?” he says at last.

Well, he is the principal, the big man, Killer Diller. How do people act around him?

“Oh, that,” he says. “Most people are used to me. It’s not that I get too many new people right now.”

I read that Mr Burns, tyrannical boss of a nuclear power plant in The Simpsons, might have been based on Diller. He oversaw the show’s creation at Fox in what seemed a huge gamble at the time.

“I don’t know. I really don’t think so,” Diller says. “I mean, I would like not to think so.”

I feel bad and try to turn it into a compliment. Every episode with him in it is better, I say, and he nods.

“He’s a good nemesis.”

A ‘sexually confused’ adolescence

Diller grew up in a wealthy, “perfectly dysfunctional” home in Beverly Hills, with a violent brother who was a drug addict by the age of 13 and parents who were always on the cusp of divorce and paid little attention to him. He grew up self-reliant and “sexually confused”, he writes.

One hot night in July, when he was 16 and driving his red Thunderbird down Sunset Boulevard, he stopped at a light and “caught the eye of a shaggy blond guy standing on his terrace. He motioned to the parking space below his apartment,” and Diller, as if “caught in a tractor beam”, parked and followed the man inside.

He does not tell us, at this momentous juncture, what was going on inside his head.

“Nothing is going on,” he tells me. “Absolutely zero. I’m very sure about this. The only thing that was going on in my head was after that one incident happened I thought, ‘Well, that’s that. I did it. I don’t have to do it again.’ ”

But about a month later, “I realised with dread that, like a serial killer, I had an overpowering urge to go back,” he writes, realising as he did so that this was “what I would want to do for ever”.

He wanted to keep it a secret for ever too, particularly after he entered the entertainment business. A book he read on the subject at his local library informed him that he had a mental illness. It must have made him more liable to question what he was told.

“I’ve never thought of it,” he says. “But I would think so, for sure.” He slaps the table, his sonorous voice booming for a moment. “The purity of the inclination, as being pure and right…” he says. “I couldn’t think negatively about that.”

He still thinks, even now, that if you are gay, “it robs you of adolescence completely”. In an early draft of the book, he says, he wrote, “You are lucky if you are outwardly effeminate and you can’t be in the closet and you survive.” He says now, “Because at least then you’re not hiding.”

The couple in the early Noughties

COURTESY OF BARRY DILLER

A friend who read it was appalled. Diller does an impression of this friend, saying, in a horrified whisper, “You can’t say that. That’s terrible.”

The other “native attraction” for the young Diller was the entertainment business. He had grown up around industry people, hanging out with Doris Day’s son and with the children of the comedian Danny Thomas. Unsure what to do when he finished school, he called Thomas, who was then performing in Las Vegas, and asked if he could get him a job in the mail room at the William Morris Agency. Thomas was their top client. “That’s easy,” Thomas said. “Can I go back to my massage now?”

The mail room was full of hungry young blades who wanted to be agents. Diller wanted nothing of the sort. He did not even need the money — he had plenty from his father, a successful builder — and neglected to cash his weekly pay cheques for the first six months until he was told off by the accounts department. He spent most of his time reading files in the company’s basement.

“I hated school; I hated homework,” he says. “Yet I got to this place where there were the files, the history of every single person in entertainment for the past 70 years. I just couldn’t get enough of it.”

He did this for three years. He felt like a student at Oxford, reading showbusiness. “It was such an extraordinary foundation,” he says. “I understood things about the entertainment business that almost no one understood.”

Some of this came through in conversations with Leonard Goldberg, a young executive at the ABC television network, who was dating one of Danny Thomas’s daughters and hired Diller as his assistant. Goldberg was then made head of programming at ABC and conferred on Diller a broadening array of assignments. One day Goldberg was amused to find his young aide going toe-to-toe with Charles Bluhdorn, the overbearing Austrian immigrant and sugar magnate who owned Paramount Pictures.

“There was this big mogul and my little assistant yelling at each other while devouring pastrami sandwiches,” Goldberg said. “Who knew?”

Adventures with Katharine Hepburn

Diller discovered that he loved confrontation. Thanks to the shouting match, ABC got the rights to air the Paramount hits The Godfather and Love Story. Diller also suggested that the television network should make its own films and was allowed to take charge of what was widely regarded as a doomed venture. The “Movie of the Week”, as it became known, drew huge audiences and critical acclaim, and Diller built a studio within the network that was eventually making 75 films a year.

Katharine Hepburn, who starred in an adaptation of The Glass Menagerie, marched into Diller’s office demanding that it air without commercials. Diller suggested they find a single sponsor and the two of them drove up to the headquarters of IBM that very afternoon to win them over.

Hepburn and Diller became friends and would go for long drives through her old stamping grounds in Los Angeles, sometimes sneaking into houses where she had lived, creeping through the shrubberies to swim in the pool.

Did you ever think you’d get caught?

“Listen, she was Katharine Hepburn,” he says. “So anybody who caught us I’m sure would have said, ‘Oh my goodness, Katherine Hepburn! Come, take my stuff.’ ”

Filming the 1975 TV movie Love Among the Ruins with Katharine Hepburn and Laurence Olivier

COURTESY OF BARRY DILLER

Diller was getting quite well known himself by then. In 1974, Bluhdorn, his partner in shouting matches, hired him to be chairman and chief executive of Paramount Pictures. At the time, Bluhdorn was engaged in a running battle with two of his own executives, Frank Yablans and Robert Evans. They had overseen The Godfather and used its success, as well as the services of a famous mob lawyer named Sidney Korshak, to secure themselves a five-year contract that granted them sweeping powers to ignore and belittle Bluhdorn and to greenlight films in which they held a financial stake.

Bluhdorn had retaliated by appointing 32-year-old Diller, from the lowbrow world of television, as their boss, but he would not allow Diller to fire them — under the terms of their contract, such a move would cost the studio millions. Diller read through Yablans’s contract. Discovering it was rather vague about Yablans’s duties, he sent a memo ordering that all staff who once reported to Yablans would now report to him.

Yablans came screaming into his office and, when Diller stood his ground, resigned.

“We have to settle this,” Korshak said, his voice full of menace.

Diller argued there was nothing to settle, while Bluhdorn, absolutely petrified, barricaded himself into his office and begged Diller to make a deal.

“That was scary,” Diller says. “Sidney Korshak was a true mob person. He was big, he had a very commanding voice and he was very theatrical in his menace.”

At one point, when Korshak stopped responding, “I sent a security guard to find out if he was OK,” he says. Korshak got on the line and warned him never again to send anyone to find him, his voice soft and sinister. “It was like I heard death,” Diller says.

A settlement was agreed, Yablans was out, and young Diller began trying to put the house in order. It was around this time, when everyone thought he was failing, that he attended a New York dinner party in von Furstenberg’s New York flat. They are like Tony and Maria in West Side Story when they meet and “everyone else fades away”, he writes. “The biological imperative [of his attraction to her] was as strong in its heterosexuality as its opposite had been.”

How did he reconcile himself to it?

In Washington with Al Pacino and Marthe Keller, Pacino’s co-star in the film Bobby Deerfield, 1977

GETTY IMAGES

“Nonplussed is not the word for it,” he says. “I was so on auto… Every once in a while, in the beginning, I thought, ‘Huh? What’s this?’ And I never examined it. I never thought about it. I just thought, ‘Well, OK.’ ”

They broke up in 1981, got back together in 1991 and married in 2001. Their 1981 break-up came after she had an affair with Richard Gere, the star of American Gigolo, a film Diller was overseeing. The role was supposed to go to John Travolta, whose parts in Saturday Night Fever and Grease had helped Diller revive Paramount, but Travolta had backed out at the last moment.

“He was afraid of playing that character because of its somewhat gay subtext,” Diller writes.

“I don’t know it for a fact,” he tells me now. But others thought so too, he adds. The other Travolta-jolter came after Diller met Princess Margaret at a dinner. She wanted to have tea with Travolta. Send her over to my place, Travolta said.

Diller explained that she was the sister of the Queen and he ought to go to her hotel.

“She hit on me,” Travolta said afterwards.

“That was so funny,” Diller says. “He truly did not know who she was.”

Hollywood power plays

After Bluhdorn died, in 1983, Diller went to run Twentieth Century Fox, discovering only after he had arrived that it had debts of $150 million and the banks were about to pull the plug. The owner, an oil tycoon named Marvin Davis with the build and manners of a grizzly bear, explained, between mouthfuls of caviar, that he had hired Diller to get the bankers off his back but he had no intention of putting in more money.

Just as Diller was preparing to take him to court, Davis sold half the studio to Rupert Murdoch, who, says Diller, cared nothing about the debts. “He would have climbed over 17 mountains to get Fox. He wanted into the United States and he wanted a seat at the big studio table.” Luckily, the Fox film Home Alone became a smash hit and made the company almost $500 million.

In 1992, Diller left to become a player in his own right. He fought a long, ultimately unsuccessful battle against the media magnate Sumner Redstone for control of Paramount that involved all manner of brinkmanship, including Redstone putting it about that Diller had Aids. He became part owner of a television network that he sold in 2005, along with a studio and the Sci-Fi Channel, for about $12 billion, agreeing the deal over the phone from the deck of his yacht in the Caribbean.

Did he watch Succession?

“I tried because everyone liked it so much,” he says. “I thought the dialogue was snappy. But the actual story was stupid and just not real. I mean, I know real, because I participated in it.”

Well, I say. Supposing you were still in charge of Paramount or Twentieth Century Fox, and I came to you with an idea for a film about this guy called Diller who becomes a mogul. What would you say to that?

He ponders for a moment. “It doesn’t have enough adversity in it,” he says.

The Little Island public park in New York, which was developed by Barry Diller and opened in 2021

GETTY IMAGES

It has some adversity. The neglected childhood, the abusive brother, being gay and afraid in Sixties America.

“I mean, first part, yes, sure, growing up. You get that over with fairly quickly in a biopic. Listen, those stories are set against great conflict, like wars where, you know, there’s stuff going on… Or they’re the story of people who are performers, so you get to show them performing to make great movies.” He shakes his head. “No, I wouldn’t make a good movie.”

Perhaps something tighter, focused on the Hollywood years?

“Yeah, all right,” he says. “Maybe a short miniseries.”

Barry Diller, the Movie?

I am hoping that we might spend all afternoon talking about Hollywood and going over my ideas for the Citizen Diller film when there is a buzzing sound. Diller stoops and reaches beneath the table and retrieves a red telephone handset on a cord, exactly like the one Commissioner Gordon uses to summon Batman.

“Yes,” he says. “OK. Um, yes. Do that.”

I wonder if a trap door will open beneath my seat, sending me down a chute into a shark tank. It does not. He puts the receiver back beneath the table and says, “OK, I have two minutes.”

I’d better ask a really big question that will wrap everything together.

Do you really have five clones of your old, beloved Jack Russell terrier?

“We have a lot of clones,” he nods.

Do they all come with you on your yacht?

Diller has a 300ft yacht named after Eos, the Greek goddess of the dawn, with a sculpture of von Furstenberg on the prow. Soon, when he has finished being grilled about his sex life, they will set sail upon it.

“Only one [cloned dog] goes with us,” he says. “One boat, one dog.”

Do they have any health issues, the clones?

“No,” he exclaims, shaking his head.

How close are we to cloning Barry Diller?

“I think very close. I’m sure it’s happening in China right now as we speak. Not me, but someone.”

When will he launch a podcast?

“Me? No, please,” he says. He gets up. “Thank you for coming over,” he says.

I’m not entirely sure if he means it.

“I gotta run,” he says. And he does. He jogs out of the conference room and a lady comes in to politely throw me out.

Downstairs, I wave to the security guard who was to inform the world of my expected disappearance. I cycle away through New York, through the places where they made something and where now they divide and sell other people’s attention: the old packing warehouses now full of tech bros.

With Dolly Parton at the benefit premiere of the film Steel Magnolias in New York, 1989

GETTY IMAGES

“They’re such large enterprises,” Diller had said at our meeting. “And, like, No 82 on their [list] is, ‘OK, what shows are we developing?’ When I was doing it, that was the only thing I cared about.”

And you had some great characters in your story, I’d said, for I was still pitching him on the film idea. Charles Bluhdorn, the Austrian who started out in the rag trade; Marvin Davis guzzling caviar; Sidney Korshak, the mob lawyer.

“I have lots of good characters,” he agreed. “I wish there were more of them. I wish they were back. It’s just so bloodless now.”

Who Knew by Barry Diller (Simon & Schuster, £20). To order a copy go to timesbookshop.co.uk or call 020 3176 2935. Free UK P&P on online orders over £25. Discount available for Times+ members