At 5 pm in early January, Wayne Diamond is in his Upper East Side apartment, holding a glass of white wine in his hand, and talking about his favorite subject, one that’s become somehow more interesting in the last few months: life as Wayne Diamond.
“It was always good,” says Wayne Diamond. “‘Oh, you’re Wayne Diamond! Oh, you’re Wayne Diamond!’ And now, I’m like, really Wayne Diamond!”
To red sauce chefs, aspiring-model maître’ d’s, garment district stalwarts, and lascivious aesthetes uptown and down, Diamond has been a familiar personality for decades, moving in a million different circles, and relied upon like a 19th century salon guest for his crass wit and a bizarrely high standard for culture and ideas. Of course, we’re talking about what it’s like to be Wayne Diamond for a different reason: he’s become known by a whole new set of fans as the ultra-tan lothario, credited as the “handsome older man,” who proves himself a late-stage hero in Uncut Gems.
No one extemporizes like Wayne Diamond, who can pivot from boobs to art in ten words or less. One second he’s talking about how you must seek out the best jacket—it’s the thing that makes an outfit, and the rest is just jeans and the right jewelry—and seconds later he’s onto television personality Donnie Deutsch, whom he calls “Donnie Douchebag”—“a total nerd.”
“He’s the downfall of men’s clothing in America today,” Diamond says. Even his suits suggest that “he has no taste level.”
Wayne Diamond is obsessed with a lot of things—wine, women, Miami, leather—but perhaps his most passionate fixation is taste. This may be hard to believe, because his hair is outrageous and his tan even more outrageous, and while we speak his tight black Theory t-shirt climbs up over his belly like it’s tangoing with your eyebrows—which is to say that his taste is not what your average 71-year-old Upper East Sider might define as good. But like a true bon vivant, Wayne Diamond has taste in everything, and he is discerning about restaurants (Bar Pitti, J.G. Melon, Emilio’s Ballato, Nello, Bella Blu...if you know, you know); and outerwear (“I love a real Chrome Hearts look,” he says, but from the ’80s, “not that new shit”); and simply how to live your life. In the words of Diana Vreeland, another charismatic uptown tastemaker: style is not “about a lot of clothes.”
The Safdie brothers populate their films with unlikely characters, village idiosyncrasies plucked from the wild and set loose upon the script. Many of them are scruffy, rough around the edges. Wayne Diamond is a dreamer and a romantic with big ambitions—shortly before I arrived, he tells me, he got a text from Sebastian Bear-McClard, the Uncut Gems producer who first introduced the Safdies to Wayne Diamond. “He wrote me…. What the fuck did he write me?” Wayne Diamond paws at his phone. “Here: ‘I’m going to change your life.’”
Is Wayne Diamond going to change mine? As our 45 minutes together stretch into nearly two hours, Wayne Diamond’s anachronistic musings slowly give way to something deeply, poetically humane. Eventually. “I think people look like slobs,” he tells me. “They don’t look good.” Men, he says, “are really sleazy today. They got their porn, they all jerk off all day long, and they don’t even have babies as much anymore.”
“Can you tell that in the way that they’re dressing?” I ask.
His publicist—an addition to the squad since his newfound movie stardom, along with two social media managers who curate a bombastically earnest Instagram account—clarifies that it’s “athleisure” he’s referring to. “Yeah, right,” he nods. “That’s disgusting.”
He continues, “First of all, I think chino pants should be outlawed in every restaurant in New York. Striped shirts and checked shirts. They should throw you out of a restaurant.” Once Wayne Diamond is off on his theory about the decline and clothes and the rise of porn—his own hemline index, if you will—it’s basically impossible to stop him. Everything moves but his hair. (Wayne Diamond says he generally does his own hair—“I get the right gel, I get the right thing, the hairspray, I hold it up, it's a whole trip to watch me do it"—though he sometimes goes to “1400 Broadway,” a place, I later find on google, called “Made Man Barber.”)
And porn has totally screwed men up: “It’s a really fucked up world we’re living in. Not morally,” he clarifies, but people “don’t get excited about the same things anymore.” Like, “when they were into art or something, they went to a museum, and they saw these [nude] women and they way they used to look, maybe they would get a better idea about life. I don’t think people read anymore, either, which is another problem.” When he was young, you had to find other ways to get off: “Like Lady Chatterley’s Lover, every guy in the world jerked off to that, but at least you read a good book!”
“We have a cultural problem in America,” he continues. “We don’t have much culture, and what we have is really not much. When you go to Europe, everybody’s dressed up in a nice jacket going out to dinner, nice jewelry, very classy. Good shoes, everything shines, looking spiffy.”
Enough complaining, I say. What are two or three things a man can do to improve himself? This seems to be something Wayne Diamond has thought a lot about. “The first thing a guy has got to do is look in a mirror at himself. And say, ‘What could I do to make myself look better?’ Even if a guy's ugly. ‘What can I do?’ That's the first thing. Just look at your body and look at your face and say, ‘What can I do with my body and face?’ Get nude in front of the mirror, he says, and ask yourself, ‘How do I cover the fat? How do I do this, how do I make myself look better?’”
Then, he says, “go maybe go to a store and say ‘These are my problems.’ Speak to the guy working at the store who can get you what you want: You really want to look good, but you don’t want to look like everybody else. You want some originality. And you want to make sure that you're wearing the right shirt with the right pants with the right shoes with the right socks.” Take yourself to the barber, “put a little tanning lotion on, smell good—don't put no perfume on, I don’t believe in that shit—just look good. Look the best you can look so you've got a shot out there.”
Go out. Forget about Tinder, J Date, e-Harmony: “I think it’s fucking awful. I don’t understand how people can’t meet each other. I can’t understand it.” Talk to women, know “when to ask a girl, ‘Hey baby, what's happening, you want a drink? Yeah, let’s sit down and talk!’ ‘What do you do?’ ‘Now I’m an actor, I used to be a garment guy, but now I’m a major actor. Look me up.’” (Wayne Diamond clarifies that he’s speaking theoretically; he is happily married.)
Wayne Diamond pauses. “I really get anxiety when I’m thinking about this,” he says. “And I know how these kids think. I sit at Bar Pitti with all these kids, and it’s really weird: they don’t even give a fuck about their girlfriends. They just go home, and they come, and they go to work, and that’s it, they’re happy. They don’t need anything but their hand.
“I think it’s a big problem,” he says. “I think it’s a major problem. I think it’s probably one of the biggest. And has to do with clothing, it has to do with fashion, has to do with everything.”
Why does it have to do with fashion? Because they aren’t dressing up to go out. “They put on their chinos, they put on their stupid striped shirts, and they go out and they're really, they meet a girl wonderful or not, they’re not looking to get laid.”
At this point, I begin to wonder if Wayne Diamond should run for office.
Just the night before, Wayne Diamond tells me, he went out with a bunch of guys who run an indie men’s magazine. He likes hanging out with gay guys, he says. “Straight people are not too interesting. All they talk about is money. These guys talk about art, they talk about theater, ballet. They talk about stuff that’s interesting.”
That’s why Wayne Diamond hated the suburbs. “Everybody’s the same,” he says. “Every conversation is about, how good was your week, how much money you make, how’s your stocks doing. I had a monster house in Westbury, a beautiful house, and probably today it’s worth about 15 mil, but in those days I sold it for six.”
“But you know, I loved it. I love flowers. I like the pool. I liked sitting there. But the people were hard to deal with. New York, I love. Wherever you go, you walk into a restaurant, they look at you. They give you this evil eye. They see the hair and shit. They say, ‘Oh, this guy’s a schmuck.’ And I enjoy it: Fuck you, too! And then we become friends.”
To back up a minute: how did Wayne Diamond own a $6 million dollar home? And this Upper East Side two-bedroom? And these John Chamberlain sketches, this Paolo Buffa chair I’m sitting in, the Willy Rizzo coffee table stacked high with glossy tomes on Valentino and Coco Chanel?
Well: “Like Mozart could do a symphony,” says Wayne Diamond, “I could design a dress.”
Diamond’s Run, the brand was called. Based out of New York’s Garment district. “I made ten million a year” when he was running the business, he says. “I did a hundred million dollars or more” when he sold the business in the ’90s, he says. He would sell a store like Bloomingdales 100 dresses, and 80 would be gone in the first day, he says.
Wayne Diamond’s dresses were of a kind that don’t quite exist anymore, priced “anywhere from, I’d say, $12.75 to $49.75”—big design at affordable prices. When I ask where they were sold besides Bloomingdale’s, he says every store “from the lowest dance hall to the highest price guys.”
“Everybody was in competition for the middle woman in America that wanted to be hip, and in the ’70s, I think I was the greatest that ever lived.” He goes on, “I had those disco dresses, I sold millions of them. Nobody even thought about disco dresses. It was the ’70s, and I made a fortune on disco dresses.”
Disco dresses, he explains, were “very similar to everything they’re wearing today. Everything's the same, nothing’s really changed. It’s just that they copy everything I made. It burns my ass.”
Like who? I ask, and he responds that he has “no respect for designers today,” but “the only one I really kind of liked was Cavalli. He was not a designer; more of a print guy. His shit sucks but his prints are excellent.”
Speaking with Wayne Diamond is like doing that bit from The Great Gatsby where Nick Carraway is so reluctantly charmed by his scammy rich titular pal that he feels a wave of relief every time some wild claim of Gatsby’s is proven true. When Wayne Diamond shows me the sales brochure for his old house in Westchester—a glowing, multi-million dollar pseudo-Mediterranean hulk with the cursive headline, “OLD WORLD ELEGANCE”—I think of Gatsby handing Nick photographic evidence of himself attending Oxford University. When I peek into the kitchen from his lounge-lizard living room, I see that every appliance, utensil, knob, and dish towel is cherry red—the safe space of a stylish Nora Ephron heroine, not a fabulist swinger. Or when I look up his dresses online and found a bunch of ruffled and lamé ’40s-inspired swing dresses covered in sequins, somehow just as I imagined them. These were the dresses, I suppose, for the woman with Halston dreams but no local Studio 54. Or Diane Von Furstenberg for the woman who couldn’t get near enough a glass ceiling to break one. As Carraway says, when Gatsby reveals that he only sort of lied about going to Oxford: “I had one of those renewals of complete faith in him that I experienced before.”
Now, of course, he’s out of the game and living more modestly, but really living. “Forget how much I spent a year—I was a gambler, that’s what cost my money. But I had plenty of money, I have no need for more. At my age, all I care about is two things: my kids are healthy, my wife is healthy, I can still get a hard on, and I’m a lesbian at heart, so I get all the necessities of being a good person.”
Would he ever go back? He teased a comeback a few years ago, but...well, now he isn’t so sure. It can be difficult and exhausting to get a straight answer out of Wayne Diamond, in part because he pivots so quickly from fact to philosophizing. “The only time you’re really great is when you’re young,” he says. “People, when they get old, they don’t become great. Not in the arts. They just don’t. Writing, maybe. But not in the [other] arts. It’s either there or it’s not there when you’re young. Tchaikovsky, Wagner, Mozart. Or you go to the great painters. How old do you think [Michelangelo] was when he was doing the Sistine Chapel?”
But that’s when people died when they were like, 40 years old.
“Right, but it’s a change. All the ideas I had were when I was young. Now I could look at them and use them, but at that age, you have them. You don’t have them when you get older. The ideas don’t flow. Your mind doesn’t work like that.”
Wayne Diamond has been having a blood pressure “thing,” he tells me, so perhaps that’s why he’s feeling a little gloomy. But now the sun is long down and it’s time for Wayne Diamond to go out. Tonight, he’s straying from his standby restaurants for a meeting with a potential partner to discuss—what else?—a screenplay based on his life.
We stand up and pull on our coats and he thinks about how life might get better. “I don’t want to think about me,” he says. “I just want to have a good time.”
