Barry Diller has only just started his book tour, but he’s already trying to sneak away.
“I’m shortening the tour part,” the 83-year-old mogul said recently in his sonorous baritone, the “Killer Diller” voice that intimidated and intrigued Hollywood for more than half a century. “I am not up for interrogation on aspects of my personal life.”
As we sat on cappuccino-colored couches in his gorgeous Art Nouveau aerie in the Carlyle hotel, I reminded Diller about the bewitchingly candid first paragraph of his bildungsroman, “Who Knew”:
The household I grew up in was perfectly dysfunctional. My parents separated often and came a day short of divorce several times before I was 10; my brother was a drug addict by age 13; and I was a sexually confused holder of secrets from the age of 11.
And there it was, Hollywood’s worst-kept secret spilled: Barry Diller is gay. Or rather, bisexual — or bi with Di, since, as he writes, “While there have been a good many men in my life from the age of 16, there has only ever been one woman.” The sultry Princess of Wrap, Diane von Furstenberg, swept him away back in the Studio 54 days. She’s proud of being the first woman he ever slept with, in a torrid romance that later unfurled into a long, happy, sexually liberated marriage.
Von Furstenberg and Diller’s friends are watching, wide-eyed, as Diller talks publicly for the first time about his unorthodox private life. The gruff, point-blank executive is known, as the Netflix chief executive Ted Sarandos said, as “one of the very few who doesn’t care what people think in a town full of people who do care.” That is true in business. But for most of his lifetime, Diller did care about what people thought of his sexual orientation.
“I wanted to tell the story,” he said about his alienated childhood and dazzling career. “And I knew if I told the story, I had to tell the truth.” That doesn’t make it easier. He’s kept his private life shrouded for so long, it’s hard now to rip off that shroud.
Even though he early on created what he calls his own “Bill of Rights,” where he would not tell many people in his business world that he was gay but would also not pretend to be heterosexual and act like “one of the boys,” he now says he was just “chicken.”
“So many of us at that time were in this exiled state, so stunted in the way we lived,” he writes. “Consider if you can what such a daily drip of that kind of dysfunctional life does to one’s sense of self.”
In his big, sprawling life, Diller has helped shape the culture across the 20th and 21st centuries, traversing the world of entertainment from a heady time for Hollywood studios to a bleak time, deftly surfing the shifts from networks to movie theaters to cable to VCRs to streaming. He was early to see the artificial intelligence revolution coming and to predict that the upstart streamers would swallow the grand old studios — the death knell for Hollywood as we knew it.
“It’s interesting that Barry spent the first part of his career building Hollywood,” The Ankler’s Janice Min said, “and the second part talking about what a disaster it is.”
But that culture has also shaped his life. His memoir is blunt, like him, with a vulnerable story about coming of age in America that stands in stark contrast to the manosphere and the cartoonish, chest-thumping, cat-lady-hating “masculine energy,” as Mark Zuckerberg termed it, being projected in Washington by President Trump, JD Vance and Elon Musk.
While there is far more tolerance now, Diller writes, he believes there is still “agonizing pressure on most young men and women at the first glimmerings of their sexuality.” He could be fearless as a young executive, he says, because his dread of being exposed as gay “absorbed most of my fear-making capacity.”
Known for boldly jumping ahead, he confesses that he should not have lagged behind in talking about his personal life.
“For too long I justified my silence by believing that my ‘complex’ sexuality would preclude me from being a poster boy for gay pride,” he writes. “In truth, I was just too chicken to tell anyone anything. I rationalized that this was an honorable position because I’d been adhering faithfully to my rules of behavior: never be hypocritical, never lie, never pose. Given all my own trauma, I believed I didn’t owe the world a defining statement. I was wrong. I should have been a role model, for whatever good that might have done for others. It’s a guilt that will never leave me.”
Diller is one of a growing number of billionaires dominating America, although he is not gleefully wrecking our government, the media or the internet, like some of his peers. His private life may be very different from that of most Americans, but Diller has shared many of the unsettling emotions that assail us all as we all come of age: shame, anxiety, unmet expectations and guilt.
He lived a double life of sorts for a startlingly long time, a choice that many young gay people would find baffling now. But that choice said a lot about America in those years — and about how traumatized Diller was by his family.
“The whole concept of coming out today is so absurd,” he told me, noting that a few days ago, when New York magazine ran an excerpt from his book and reporters began jumping on the story, “Diane calls me laughing and saying, ‘They called and asked me about your coming out.’” They both thought it was “silly” that it made news. “I’m getting congratulations literally from people I don’t even know,” Diller said.
Scott Rudin, who was the young head of production at 20th Century Fox during Diller’s stint as chairman, said that being a gay Hollywood executive back in the 1970s and ’80s was tricky.
“Being gay was perceived as a deficit, something that would hold you back if you were the public face of a big company,” Rudin said. “It required a level of strength and fortitude if you were not welcomed in the club you were expected to be in.”
Despite the passions he had to constrain, Diller’s fervor for work was intense. While he operated with private fears about his sexuality, his ferocity in business over big deals and small matters of office etiquette provoked fear in others. “Yes, absolutely,” he told me, “I’m a difficult manager.”
John Malone, the wizard of media investments who has worked on deals and served on boards with Diller — they even sued each other a couple of decades ago — calls Diller whip-smart and said he has “matured” in terms of being impatient with those who don’t get things as quickly as he does.
“I’ve never been more intimidated by anybody in my life, with the exception of maybe Nelson Mandela,” Diller’s friend Oprah Winfrey said. “I was like, ‘Gayle, you sit next to him.’” When she got to know him, she said, she found an unlikely sweetness and soulfulness.
From a tender age Diller was a visionary of culture, and he later immersed himself in technology. He was ahead of the curve, ignoring naysayers and second-raters who insisted his innovations were impossible. As a wunderkind at ABC, he conjured the enormously successful “Movie of the Week” and the mini-series, airing “Rich Man, Poor Man,” “Roots” and “The Winds of War.” At 32, he was the youngest chief executive Paramount had ever had, and at a time when movies were vital, he turned out hits like “The Godfather, Part II,” “Saturday Night Fever,” “Grease,” “Raiders of the Lost Ark,” “Reds,” “Terms of Endearment” and “Beverly Hills Cop.” Working with Rupert Murdoch at 20th Century Fox, he midwifed a fourth broadcast network, which everyone thought was impossible, and spiced it up with shows like “Married With Children” and “The Simpsons.” (It is said that the rich, dastardly, bullet-headed boss, Mr. Burns, is inspired by Diller.) He only used his instincts, disdaining research data and dreading algorithms.
When he asked Murdoch if he could become a principal at Fox, the Aussie’s answer was pure Logan Roy. “There’s really only one principal in this company,” Murdoch said, adding, “This is a family company, and you’re not a member.”
As Diller writes, “Rupert the Sun God” had “gotten what he’d needed out of me and now we were on cruise control — a dangerous place in Murdochland.” He decided to leave.
Von Furstenberg told Diller about QVC, the home shopping network where she was selling her wares. Diller was amazed that the station was selling goods directly to the public, so he bought into it.
“People ridiculed him for being in Shmatteland,” his longtime friend Marlo Thomas told me. “He instinctively knew there was something there, and he was going to investigate it and learn about it. He was willing to end up in a dead end. He was curious and excited, and that’s the essence of Barry.”
Diller used QVC as a launchpad into interactivity — buying Expedia Group and Ticketmaster, and acquiring dating sites like Tinder, Match.com. and Hinge, as well as the Home Shopping Network. He took over the USA Network and instructed Dick Wolf to lean into the “Law & Order” universe, which is how we get to watch Mariska Hargitay say “Where were you last Tuesday?” pretty much 24 hours a day.
Just when Hollywood thought that Diller was relegated to the margins, on his way to what we now call being Quibied, he whipped the hodgepodge of digital sites into the powerhouse IAC. In 2020, he spun off the dating sites and then doubled down on digital content, acquiring the Meredith Corporation, which publishes People, Better Homes and Gardens and Southern Living. He also owns The Daily Beast.
Even though he doesn’t gamble, he now thinks the future is in Las Vegas, with all the new sports teams there and all the stars in residence. He bought into MGM Resorts, a conglomerate of casinos, hotels and entertainment venues.
His book is a saga of inventing this enormous, original career that spawned so many cultural touchstones. But he also talks about his fears, his childhood nervous breakdown, his failures, the times he cried.
He grew up in Beverly Hills, the son of a builder who became affluent constructing indistinguishable tract housing on streets with names like Dillerdale and Barrydale.
Reading about Diller’s disconnected relationship with his family, it’s easy to understand how he fell for the woman he calls “an earth mother.” His home was airless, sterile and filled with pain.
He said that his father didn’t know how to father, his mother didn’t know how to mother and his brother didn’t know how to brother.
His noncommunicative father was in business for 30 years with his uncle, who lived two blocks away, but the families never socialized. “I also never met my paternal grandparents, or most of my aunts, uncles and cousins,” Diller writes.
When he was 7, he was lonely at camp and begged his mother to come pick him up; she left him waiting outside in the dark.
“I gave up on my mother that night,” he writes. “There would be no rescue.”
At 11, Diller rode his bike down to the Beverly Hills Public Library. “I furtively hunted the shelves for books on homosexuality,” he writes. “In each one, chapter after chapter hammered home to a frightened child that all such activity was a result of mental illness. It was a disease!”
He added, “I had to compartmentalize my sexual feelings to keep from being branded forever as abnormal.”
He became obsessive-compulsive, feeling like there was “an anvil hanging by the most tenuous wire over my head and the discovery of my sexuality would snap that wire and the anvil would come crashing down.” At 19, he writes, he had “an actual heart-and-mind-racing nervous breakdown.” The family doctor put him on a maximum dose of Valium; he was “living like a zombie,” indulging in “all-night wanderings and all-day sleeping.”
Diller’s older brother, Donald, was smart and handsome, a piano prodigy. But around puberty he became “gruesomely and violently abusive” to Barry. Once, his brother “took one of those old heavy Bakelite telephones and twirled it around like a lariat, finally landing it on the side of my head, knocking me out cold.”
“To him I was dumb and clunky, and probably homosexual,” Diller writes. “All this planted a corrosive and deep seed in me that there absolutely shouldn’t — there couldn’t — be two ‘bad’ sons. One a drug addict and the other a sexual outcast.” This fear, he said, “was the dagger to my heart.”
By 16, Donald was hooked on heroin. The brothers were estranged. At 36, Donald was shot and killed in what police called a “drug-related incident.” Diller wrote that he still feels bitter toward him.
At Beverly Hills High, Diller’s friend Nora Ephron fired him from the school paper because he wasn’t serious enough. He said that even when she was a teenager, Ephron, the tart-tongued daughter of screenwriters, could disdainfully dissect a Hollywood party. “She was my first dose of sharp, critical dialogue,” Diller told me.
Diller didn’t care about a college degree. He asked Marlo Thomas’s father, Danny, the king of sitcoms, to help him get his first job in the William Morris mailroom.
He worked his way up as a personal assistant to big shots. He had trained with his family at trying to please the hard-to-please.
Ignoring advice from his friends, Diller called his autobiography “Who Knew.”
“Because so much of my early life was, who knew, first of all, about me and my confused sexuality?” he said. “Who knew that I had any talent?” But lots of people knew both things, actually, so he left off the question mark.
Did Diller worry that his lack of candor about his personal life would leave him vulnerable to sexual partners blowing the whistle on him?
“Oh, my god,” Diller replied, laughing. “If I’ve been closeted for decades, that closet has the brightest light and glass door anyone has ever seen. That is so beyond insane.”
In 2015, when Trump was first running for president, Diller said in an interview that he might leave the country if Trump won because “all he is is a huckster” who found “a vein of meanness and nastiness.”
Trump tweeted his response to “Little Barry Diller,” saying “he is a sad and pathetic figure. Lives lie!”
I asked Diller how he felt when he read that tweet.
“I laughed,” he said, “because it was so consistent with his manner of attack.”
Diller saw some striking examples of homophobia in Hollywood.
In 1974, he heard that People magazine was planning to do a “mean and homophobic” story on him. In the end, it just dissed his business acumen, saying he had failed upward. He said he was relieved because in those days, it was “better to be called a failure than a fairy.”
“By the way,” he writes dryly, “I now own People magazine.”
When he was the chief executive of Paramount, he learned that two of his executives were stealing from the company. One of them threatened that if his bosses went to the authorities, he would concoct a story about his 11-year-old son, claiming that Diller had molested him in an elevator. They turned the man in; he pleaded guilty to criminal charges and later came out as gay himself.
Diller writes that when he was at QVC in 1994, in a hot competition with Sumner Redstone to acquire Paramount, rumors began circulating about Diller and AIDS. A New York Times reporter called Diller to ask about his health. Shocked, he replied that he was fine.
James Stewart wrote in his 2005 book “DisneyWar” that in 1995, when Diller’s friend Michael Eisner was asked to name a potential successor as chief executive of Disney, he threw out Diller’s name in a confidential memo to the board, noting, “He is not a family man, but I believe you do not have to be a chicken to know a good egg.” He added, “the fact that he is homosexual should have no weight,” in effect, outing him to those who didn’t know and dooming his chances.
Diller settles a few scores in the book, but mostly he tends to be forgiving. He praises Eisner and says he regrets some of the harsh things he has said about his old boss Murdoch.
“I went on a podcast and said Rupert is the suck-up of all time,” Diller told me. “He’s always been a toady to power. Whoever’s in power, he’s right there at the first moment.” He also said the “horribleness of Fox News” would be a stain on Murdoch’s legacy.
I tweaked Diller that in helping to create the Fox network and the pioneering reality show “Cops” — not to mention helping Murdoch establish himself in American TV — he paved the way for Trump.
He said that Fox News came after he left, but he did admit to one damning thing: “I introduced Rupert Murdoch to Roger Ailes.”
He defended his “very, very dear, loving friend” Jeff Bezos, for embarrassing The Washington Post and driving away a lot of its talented writers and editors when he killed the paper’s Kamala Harris endorsement and told its opinion editors that they had to cleave to the principles of free markets and personal liberties.
He thought the policy of not endorsing for president was fine, but the timing was “unfortunate” because “it would have been better to have done it six months before, when it wasn’t so close to the election.” As to the instructions for opinion writers, Diller played the contrarian, as he often does: “I think it is an utterly principled position.”
He also defended Shari Redstone — he dealt with her when he took another swing at buying Paramount last year — for being willing to cave to Trump on his “60 Minutes” lawsuit to clear the way for Paramount’s merger with Skydance.
Although “the idea of settling this idiot suit is horrible,” he said, Redstone has financial problems “and made this deal to get bailed out by the sale.” It’s understandable, he said, to “bend the knee if there’s a guillotine at your head.”
Diller, who was a generous Biden donor, said he blamed Joe Biden more than Trump for Trump’s election.
“I’m so angry at the Democratic progressivism and elite nonsense of the last decade,” he said, adding: “I hate the woke right as much as I hate the woke left. A ban on both their houses.”
At our interview, over a lunch of Cobb salad and grilled cheese sandwiches, I note that Diller does not seem as nervous as he did the last time I interviewed him, when he broke out a pack of cigarettes.
“I came close to dying,” he said. He tried to stop smoking and started vaping a lot, and his lung collapsed.
“Anytime I see somebody vaping,” he said, “I go and try and take it away from them.”
Diller is still bristling with ideas. His foundation is building a park at the top of Franklin Canyon, north of Beverly Hills. And Diller and Rudin are talking about opening a complex of five Off Broadway theaters in Manhattan. Diller is also exploring buying Candy AI, a site that creates any avatar you like.
“The big story of my life,” the man famous for spinning 1,001 stories told me, “is Diane and my family.”
And his five cloned dogs, of course. He found the original, Shannon, a homeless Jack Russell terrier, wandering a back road in Ireland long ago. He loves the dogs so much, he took one of Shannon’s progeny, Dina (inspired by DNA) back to Ireland to discover her roots.
David Geffen, Diller’s best friend, observed that while the von Dillers, as the superagent Sue Mengers called them, may not be a “run of the mill” family, their alliance is full of love and joy and charity.
“I think being with Diane, her children and their grandchildren has mellowed Barry tremendously,” Geffen said.
What was he like before? I asked. Geffen laughed and replied, “Less user-friendly.”
And certainly, the frank von Furstenberg is a match for the blunt Diller.
Diller told me of taking his wife out in a boat on the Hudson to see his celebrated new office building in Chelsea when it was completed in 2007, so she could be on the water when she saw it, a Frank Gehry creation designed to evoke a tall ship in full sail.
“I say to her, ‘Isn’t that gorgeous?’” he recalled. “She says to me, ‘It’s too short.’ I say, ‘What?’ She says, ‘It’s too short. We should build it up another four stories.’ I was so angry that she said about my beautiful, magnificent building in perfect proportion, ‘It looks like it was collapsed.’”
When they’re not sailing the world on their Art Deco yacht, the Eos, or ensconced in their Connecticut estate, Cloudwalk, or holed up in their dreamy Beverly Hills mansion, or dining al fresco at the Venice palazzo Diane has been spending time in, or planning a Miami family compound, the pair live separately in their art-filled Manhattan apartments. His is uptown at the Carlyle and hers is downtown above her flagship store in the meatpacking district.
Their romance in the ’70s ended painfully for Diller; they were drifting apart, but then he learned that von Furstenberg had dallied with Richard Gere. Diller was the 33-year-old head of Paramount at the time, and Gere was the sexy star of one of his pictures, “American Gigolo.”
“It was a little … nothing,” von Furstenberg murmured when I asked her about it.
A decade later, Barry and Diane got back together, and the rest is part of New York City history. Their foundation funded two of Gotham’s most popular and enchanting downtown attractions: the High Line and Little Island, which has an amphitheater for plays and concerts. When people began referring to the site as “Diller Island,” Diller shuddered. Unlike other billionaires, he does not want his name plastered on things, even when they cost, as Little Island might, in the end, between $400 million and $500 million.
Both von Furstenberg and Diller say they did not talk about his sexual confessions in the book or revelations about his gay liaisons, including one with Johnny Carson’s stepson and one with Michael Bennett of “A Chorus Line” fame, both of whom died of AIDS.
“It’s something I’ve never discussed with him,” von Furstenberg said. “Because what is between him and me is so much more. It’s so much deeper.
“But, you know,” she added, “I’m an odd cookie.”
She recalled her beginning with “my little honey”: “Barry was very shy, very reserved, never talked, never opened up about anything. With me, for whatever reason, he opened his heart fully — boom! — and never closed it. Even when I made him suffer, he never took it back.”
“The only time we ever talked about our relationship,” Diller said, “is when she left me.” That was during the turbulent period when he refused her entreaties to have a child, and she frolicked with Gere and then moved to Bali and took up with a beach boy named Paulo, launching a perfume inspired by Paulo called Volcan D’Amour.
“I wish I was not such an immature child as to not have a child with her,” Diller told me, noting that he was scared of settling into “suburban somnambulance.” “I lost myself on this idiot idea that I would be driving a woodie in the San Fernando Valley.” (As though von Furstenberg is capable of driving a station wagon through suburban somnambulance.)
I called Diller when he got back to Los Angeles to see how the book tour was going.
“If I let them,” he said dryly of his publishers, “they’d send me to a yeshiva in Oshkosh.”
He said he was under his bedcovers, with a cup of tea and his dog Luna.
“It’s too much,” he deadpanned, “for little me.”
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Maureen Dowd is an Opinion columnist for The Times. She won the 1999 Pulitzer Prize for distinguished commentary. She is the author, most recently, of “Notorious.” @MaureenDowd • Facebook
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