Some billionaires collect yachts, others buy islands, and then there’s Barry Diller — a man who built a media empire, married a fashion legend, and spent a lifetime quietly hosting a private Pride parade in the back of the Carlyle.
Now, at 83, and just in time for his memoir Who Knew (May 20, mark your calendars, gays), Diller is cracking open his crystal closet with a wink, a sigh, and a perfectly folded Hermès pocket square.
RELATED: Barry Diller Comes Out at 83: A Billionaire Love Story Defying Labels
For years, Diller’s sexuality was the worst-kept secret in Hollywood — not because anyone was hiding it particularly well, but because it was wrapped in the kind of discretion that only billions of dollars and impeccable tailoring can buy. Or, as Diller puts it with an eye-roll-level flourish: he was in a “brightly-lit, glass closet.”
But now? The lights are up, the glass is shattered, and the tea is steaming.
“I wanted to tell the story, and I knew if I told the story, I had to tell the truth,” he told The New York Times.
That truth includes some jaw-dropping name drops (of course it does — this is Barry Diller). There’s Michael Bennett — the brilliant, tortured genius behind A Chorus Line — and possibly Joe Holland, the late stepson of Johnny Carson. Neither relationship is confirmed with full chapter-and-verse detail, but in classic Diller fashion, the suggestion is more elegant than any confession. He doesn’t spill, he spritzes.
And while Hollywood was busy trying to sniff out his truth (a homophobic People piece in 1974 thankfully flopped), Diller kept building the empire. But at what cost?
He knew he was gay by 11, he says, but coming out back then would have meant shame — not just for himself, but for his parents, already grappling with a troubled older son. “Better to be called a failure than a fairy,” he told the Times. That line isn’t just heartbreaking — it’s a stinging reminder of the choices queer people once had to make between authenticity and ambition.
Still, Diller made it work in his own Diller-esque way. He stayed closeted, but not invisible. He courted glamour, held court in high places, and — in the ultimate gay plot twist — married Diane von Furstenberg. Not just any woman, but the woman who invented the wrap dress and flirted like it was a contact sport.
“I was standing alone next to the fireplace feeling I did not belong in this group when ‘Prince’ Egon von Furstenberg walked up to me and said, ‘Your pants are too short,’” Diller recalls of his first encounter with Diane at a Manhattan dinner party.
A year later? She was all over him. “We stood at the door, and I said, ‘I want to call you,’ and she said, ‘I want you to.’” Call it a meet-cute fit for a Vogue cover story — or an HBO miniseries.
Their marriage? Technically real, logistically separate. He lived uptown at the Carlyle. She, downtown in the Meatpacking District. Theirs was a bond that made no sense and perfect sense all at once — a union of respect, glamour, and maybe just a hint of “don’t ask, don’t tell.”
Even Disney couldn’t figure him out. When Diller was up for CEO, his friend Michael Eisner wrote an internal memo outing him: “The fact that he is homosexual should have no weight.” Oh, Michael. It absolutely had weight. Enough to crush that opportunity entirely.
And yet, Diller persisted. And now, finally, he’s telling it all — not with bitterness, but with the kind of late-life reflection that only an octogenarian mogul can afford.
He’s ashamed he didn’t come out sooner. We wish he could’ve been a role model. He didn’t want to be “broken.” And yet, through that pressure, he became unbreakable. What a very gay paradox.
If you’re wondering what the queer takeaway is here, it’s this: Coming out doesn’t always happen at prom. Sometimes it happens in a penthouse, with a publishing deal and a personal invite to the Met Gala. Sometimes it takes 83 years — but when it happens, it’s still powerful.
Barry Diller didn’t blaze a trail. He paved it quietly, under velvet ropes and million-dollar contracts. And now? He’s adding sequins.
Are you curious about what the rest of his book might reveal?
Source: DailyMail
He was a coward, while others like me were working for our rights, he hid behind his money, power and wife.
The title should be:
Once a coward always a coward.