Uncut Gems’s “Handsome Older Man” Wayne Diamond Establishes a New Legacy

Wayne Diamond is aptly credited as playing the “Handsome Older Man” in Uncut Gems, the buzzed-about Safdie Brothers film that follows a Diamond District jeweler (Adam Sandler) chasing his riskiest wager yet—one that will either clear him of his debt or bury him beneath it. Diamond, a Garment District legend with a permanent tan, lends more to the film’s ultimate gamble than his generic designation might imply. He becomes the final act’s unsung hero when he asks Howard’s girlfriend (Julia Fox) up to his hotel suite, unknowingly enmeshing himself in the middle of Howard’s heist. Uncut Gems has an extensive mèlange of similarly iconic New York personalities in their first film roles, from Kevin Garnett to the Weeknd to Mike Francesca. But it’s Diamond who ultimately steals the show.

Of all the off-screen personas in Uncut Gems, I knew next to nothing about Diamond. The internet offered piecemeal fragments. His Linkedin reads, in all caps: “I WAS THE GREATEST DRESS DESIGNER AND MANUFACTURER OF THE 80[s] AND 90[s].” And a four-minute YouTube documentary titled Wayne Diamond Is Back! informed me that, after 30 years in the Garment District, “Wayne made over 100 million dollars and retired.” None of it confirmed anything beyond conjecture, but word of mouth seemed proof enough that Diamond had made some kind of legacy for himself, one relatively untraceable on the internet but kept alive by the people who know him. Diamond’s Instagram activity is an inadvertent meme that, upon discovery, will surely have the internet flocking mad. He tells me he pays “two of the best guys” in social media to run it, and I don’t believe him. He also tells me he never touches the app, but it’s where I manage to reach him directly—in his DMs. I suggested Cafe Jax at one, he suggested Bella Blu, his friend’s Upper East Side Italian restaurant, at two.

Diamond has an unmistakable appearance. Upon arrival, I find him at Bella Blu talking to the bartender louder than most yell. He dons his usual scarf, sunglasses, and thick coiffure. He’s aware of his “cartoon” presentation: outward, outspoken, and astonishingly sincere. You may not agree with everything he says, but you must appreciate that he’s laid it all out for your scrutiny. When we sit down at a table, his skin blends into the restaurant’s dark wood panelling. He’s drinking vodka. I don’t know the kind. The waiter approaches us, but Diamond asks me what I’m getting before he can.

“Whiskey on the rocks.” 

“What the fuck is whiskey?” he says. I scan the shelf behind the bar.

“Jameson on the rocks.”

“I live on it.”

By the end of all this he’ll have drunk a glass of their heaviest red and three glasses of vodka. It’s 2PM on a Tuesday.

———

[I hit record] 

WAYNE DIAMOND: No. Listen. What are you gonna do? You’re gonna record this? Now I gotta be careful, I gotta be real careful now. 

AARON HUNT: People twisting your words?

DIAMOND: I learned a lot in the last five years.

[To the waiter] You know what I’d do, now that I’m thinking about this shit? I’d like to have this [points to the pizza on the menu] without the cheese. Just the way it needs to be, without all that shit on it, a pizza. I want a whole pizza, just like this.

HUNT: You know everyone around here?

DIAMOND: I know everybody in fucking New York! I grew up here. I’m a club guy, I was a lunatic, I was into drugs, I did everything. I was the biggest guy in the Garment Center years ago. I was like Pied Piper to the Sicillian kids, the Italian kids, because I did very good and was very generous. Meyer Lansky [The infamous “Mob’s Accountant” of the Italian-Jewish mob] was my partner. He put me in business with Marie Oliphant [a seamstress] in the Garment Center. If anybody ever knew what was the right thing to do, was it Meyer Lansky. I mean, he’s the greatest human being who ever lived.  

HUNT: Are you married? Kids?

DIAMOND: I’m married twice, married now for forty years almost. I’m happy. I’ve got four fuckin’ kids, all Ivy league. I got one kid with street smarts like me, Brookie, and the rest of them have no fuckin’ street smarts, which, you know, is a big fuckin’ problem. If you don’t get street smarts growing up in New York, I don’t get it. Street smarts are the most important thing in the world. 

My parents were both college professors, and I love learning. I was ADD most of my life and then my daughter went to Harvard and she used to send me all the books. I started getting into all sorts of plays. I like Chekhov, I like Shakespeare, I liked everything. I started getting so entrenched in that, and when I retired about 25 years ago from the dress business, sold most of my business, I was depressed for like 5 years because it was a big business. I was important. So you start to feel like you’re not the most important thing on earth. But then I started getting myself pretty much together. I didn’t care about any of that shit anymore. 

[To the waiter] I just want a pizza with nothing on it! You know, like you just gave me here? I’ll take another fuckin’ vodka though! That’s for sure. 

Another 150 calories. I count my calories! I count every fucking thing I eat now.

HUNT: Was acting your first venture in retirement, or were you trying other things?

DIAMOND: Look, all summer I’m in Europe. I do the Hamptons for three to four weeks. I don’t like it, it makes me vomit. I like New York, and I’m in Miami 15 days every month for five months. I used to live in a place called Fisher Island for 20 years, major real estate there, 8-9,000 square feet right on the ocean. I sold my house in Owslebury. I don’t want any pressure, I just love talking to people. I got Nico in New York [Nicolas Heller], who I love, Mister Mort [Mordechai Rubinstein]—these are all the guys on the streets of New York takin’ pictures. My daughter’s a very famous artist. 

HUNT: What does she do?

DIAMOND: She does uh… artistic shit. [Laughs]—Photography! She’s the head of the art department at the University of Pennsylvania for photography. And the other kids are into other areas.  

HUNT: Did you have an early interest in the dress industry? Can you say more about how you got into that with Meyer Lansky?

DIAMOND: [Licks his fingers] I was hitching. I was a pretty poor kid. My parents were schoolteachers and in those days they didn’t make a lot of money. So I worked selling bagels—whatever I fucking had to do I did to make some money. And I took a bus—all these rich motherfuckers on Long Island, who I just wanted to bury one day in my life, because they were just not the nicest people I knew—I ended up taking the Greyhound bus to Miami where I met Meyer Lansky. I signed his name at the Eden Roc [a luxury hotel in Miami, part of Lansky’s extensive real estate], because I had no money. I was a 90-pound kid with long blonde hair. They started calling out names, they called out Meyer Lansky’s. So a little 5 foot guy comes up to me and says “You signed my name?” And I said “Oh. I’m really hungry. I just rode the bus for 24 hours.” 

He was really nice. We talked for a long time. He asked me to add a lot of numbers up and I did that. And he said “Call me when you get out of college.” Three years later I call him, ’74 I think, and he puts me in the dress business with Marie Oliphant. I became the greatest dress designer. Now, I don’t wanna sound like that scumbag Donald Trump, but I mean I was the best. I really was the best. [Laughs] So I designed millions of dresses, I mean thousands of dresses, and I became the biggest and everybody loved me and I was the easiest to get along with all the guys. Bad, good, I don’t care what the fuck they did. People are people. As long as they’re nice to me, I don’t give a shit what they did.

I always loved acting. I did a couple of plays when I was really young in junior high. I always wanted to be in a major movie role. I did a lot of little roles with the Safdie brothers, a lot of videos. 

HUNT: How’d you meet the Safdies?

DIAMOND: I was bombed one night. I saw Sabo, Sabo’s father, and Josh one night at the Spotted Pig down in the West Village. So we were all talkin’ having a good time, walkin’ out. Sabo’s father is a real sweetheart of a guy, a really great artist. Nobody knows yet, but he’s great. We know he’s great. 

HUNT: Sabo?

DIAMOND: Sebastian mmm… Mcclatta [Sebastian Bear-McClard] and Margot Razakowski [Emily Ratajkowski] or whatever. They’re all lovely, listen, I’ve never met nicer people in my life. They all love me. The reason I think they make good movies, the Safdie Bros and Sebastian—they did Daddy Long Legs and Good Time—is that they make all of the actors they’re using feel so confident in themselves, so the best of who they’re dealing with comes out. It’s like when you’re a highschooler and the teacher gives you a pat on the back. That’s the kind of guys they are. 

[The waiter brings a small plate of Wayne’s as ordered cheeseless pizza.]

DIAMOND: I wanted a whole pie! Matzah pizza, Matzah pizza! So that’s what I loved about them. I felt so myself. It’s a very serious movie. Adam Sandler is the most wonderful person I’ve met in my life. His wife is lovely, great family guy. The Safdies, Josh, and his brother, Darius [Khondji] the cinematographer—everybody was pumping for each other. It was like a communal exercise. It was like being on a kibbutz, everybody was working for each other. It was on my bucket list and I did it. I’m happy, and now it’s over. I wish I could do it again. I’m depressed it’s over.

HUNT: You’re going to keep doing it, right?

DIAMOND: Of course, of course! I’d love to do a million of these. Gimme a break, I love this shit.  I love working with young people. Young people are the future, and we’re living in a very horrible time. The inequality of wealth, the trust fund pieces of shit babies that are running around making everybody look like they’re a piece of shit. I lived in New York all my life and it’s horrible, it’s really not fair. Everybody feels like they have no opportunity. But you gotta really work harder, you know? Cuz you got all these assholes running around New York, these trust fund scumbags.

HUNT: You grew up resenting these rich assholes—

DIAMOND: No, no, not rich. It’s not because they’re rich, it’s because they have so much potential and they don’t use any of it. It has nothing to do with money, it’s that they think that’s the only ultimate goal. The ultimate goal is to feel well and feel good about yourself because you did good, not because your fucking father or grandfather did good. It has nothing to do with money. 

HUNT: But seeing that motivated you to do it differently? To strike it big in a better way?

DIAMOND: For me, I had nothing to gain, nothing to lose, I just had a good feeling about myself. The movie made me feel great about myself, it gave me self-confidence. I invested my time in a lot of young people, they all liked me, they all had fun with me, it was a great time, and I’m a great comedian. Everybody was laughing all the time. You should’ve seen the camera crew—Dario (Darius), these things weigh a hundred fuckin’ pounds and they’re carrying this shit all day. It’s hard to believe how these guys work. Everybody was working so freaking hard. I love to see people go for it. The writer Ronny Bronstein is a guy that I’ve known since a kid. He couldn’t believe I was in the fuckin’ movie. I know Ronny from Oceanside, Long Beach.

HUNT: I hope he directs again. I liked Frownland.

[Long pause]

HUNT: You know what I’m talking about, or no? 

DIAMOND: I have no fucking clue [Laughs]. I know what the Safdies did. I know my favorite movies. My favorite movie is Once Upon A Time In America. That was my favorite director, man, what was his name?

HUNT: Sergio Leone.

DIAMOND: Sergio Leone, nobody better. Once Upon A Time In America shoves Scorsese up your ass. Leone had the best movies. The Good, The Bad, And The Ugly, I mean forget about it. It is what it is, the greatest. I mean, Scorsese’s good, but it’s the same shit. 

HUNT: What do you think about the fashion in Uncut Gems? 

DIAMOND: They got so much talent, these guys, but they’re really not good dressers. They wanted me to wear some like 150-pound leather pants, like what the fuck? I went to Chrome Hearts to get a nice pair of leather pants, but they said too much money. I said okay, so I wore my black jeans and a leather jacket. I got my own shit. I don’t need their shit. I dress the same all the fucking time. But [the Safdies] are so talented they’re gonna go big. I hope to god Adam gets the Academy Award. He was different, he was serious. Julia [Fox] was great, and it’s her first movie. I’m up in that helicopter laughing for three and a half hours, I thought we were gonna crash. That one minute scene for three-and-a-half hours! I’m in this fuckin’ helicopter, guy’s feets are on my shoulder talking to this girl and nobody can hear shit—we had to do a voiceover [ADR]. What the fuck was I doing there? I’m scared of heights doing this shit! I had them laughing so hard in that helicopter, the driver was laughing his ass off. He couldn’t breathe.

[To the waiter] Glass of the best red wine. You got a heavy red wine? I gotta cook today too.

The Weekend is the greatest guy. Garret [Kevin Garnett] was unbelievable, what a nice guy. Stanfield, great. Who was also great was, what’s his name, the guy who was in Beautiful Boy? My wife and him went viral.

HUNT: Timothée Chalamet.

DIAMOND: Timothee Shimett! 

HUNT: Chalamet, yeah.

DIAMOND: He was with us the whole time at the party, you saw the fuckin’ tape of the party right? I’m in it all the time, I’m the main guy! My wife was there holding [Chalamet] up for two hours. Nobody knows who it was holding him up, but if anyone asks you, you can tell them it was Helen Diamond, for two-and-a-half hours. 

HUNT: What does Helen do?

DIAMOND: She’s a home lady, she takes care of me. I take a lot of caring for.

HUNT: I can imagine. 

DIAMOND: My wife’s like my nurse. Takes care of me. Good woman. Great woman.

HUNT: How’d you two meet?

DIAMOND: I needed a date and I was going out with all kinds of sleazy women. I had all of these women coming to my apartment. These women, they liked to do Qualuudes. It was the old days! It was a long time ago! Whatever! There’s this guy, an accountant down the hall from me, a real nerd, and I said to him, “Listen, I need a nice girl to take to an affair.” He said, “No problem, but I’d like a couple of those broads coming into your apartment.” So I said, “No problem, you get your two and I get a nice chick.” So we made a swap. I got him two chicks, gave him a couple of Quaaludes. I got on the phone with her and did the whole fuckin’ thing ‘til I won the battle with her. She ended up coming to the party I wanted her to come to and that was it. We got married and had four to three kids. [Not a typo.] That’s really the story. It was all fun. Life is fun. 

HUNT: And your kids are growing up with money. How do you spare them the nepotism you resent?

DIAMOND: I don’t want ‘em in my business. I didn’t want ‘em around, that’s why I got rid of my business. Look, I think you have to give your kids … They’ve got whatever talents they got. Leave your kids alone and let them do what they wanna do. Once you give kids money, like these schmucks do here, they’re never gonna do shit. They’re gonna do the same shit you did, they’re not gonna understand when you make mistakes. Life’s a process, and you have to go through this process in order to feel good about yourself and to create talent within yourself. That’s what I believe, anyways. 

And that’s it! I’m happy I did the movie! I wanna do some standup. I love the Fat Jewish, he’s my friend here. I fuckin’ love the guy! I belong to the Friars Club. Terrific! Last night I saw ‘em. Great comedians. I respect these guys. They get up there they just do it. Boom! Boom! Boom! I’ve gotten up and done stand up and gotten on a roll and people are laughing their asses off for a half-hour. 

And there are times you’re up there, you’re at a shithole somewhere and everybody’s like, get this fuckin’ asshole off the stage, you know? You gotta take the good, the bad, and the ugly. Sergio Leone, that’s why he made The Good, The Bad, And The Ugly. That’s the bottom line. 

HUNT: So you did a little standup?

DIAMOND: Listen, I did, but I don’t do standup as a hobby. I don’t wanna kill myself. I don’t wanna be miserable my whole life. To do standup you have to be a miserable human being. I saw Seinfield. We were so lucky, I took a bunch of actors with me about eight weeks ago, and all of a sudden my friend Nicky Petito—he’s a comedian—he was on, so I just wanted there to be enough guys so he could get on stage. And who walks up on stage for an hour? Jerry Seinfield. It was the greatest. One hour Seinfeld for free. The guy did his new Vegas show. It’s unbelievable. The timing is impeccable.

HUNT: They really workshop and shape that stuff.

DIAMOND: Nah, it’s automatic! Rodney Dangerfield’s my idol. Rodney always had it! It’s boom! Boom! Boom! It’s like, what the fuck! 

HUNT: What else are you trying in retirement?

DIAMOND: I try everything! Whatever it is I have to do. I just got a phone call from my friend. He’s got a big brand name and he wants to use me as his main guy for commercials. I’ve been wanting to do this shit! I just don’t wanna make dresses. They all want me to make dresses. I’ve got offered millions of dollars a year to make dresses. I don’t wanna do that shit no more. I did it already. It’s not about the money. I got the money. I wanna do something that excites me! Something that’s a challenge! This [Uncut Gems] was a challenge! My back is killing me and I’m carrying two forty pound bags of money! I mean, gimme a break! Horrible. I had a great fuckin’ time.

I gotta say, it was one of the three best times in my life: My kids being born, my Bar Mitzvah, and this fuckin’ movie. That’s the three best things, I tell ya. It was the biggest high I’ve had in my life. They’re all telling me how great I am! I mean, I don’t think I’m that good. I thought I was an asshole! 

HUNT: Your Linkedin says, “ I’m retired to acting which I’m ok at…” Why just okay?

DIAMOND: Because I don’t think any actor thinks they’re good. I don’t think it’s that kind of profession. I guess if you’re a guy like De Niro, or Adam Sandler, or Seinfield … If you look at, not the dollars they made, but the audiences they control, then you should feel like “I made it.” That’s really it. It’s the audience. The audience, that’s your win. If the audience loves me, I’m home, I did it! I don’t know how I did, but people seem to love me in it.

HUNT: You don’t have to do much.

 [Laughs] ‘Cuz I’m a fuckin cartoon? [Waves his hands over himself.]

HUNT: Anything aside from Uncut Gems stand out as an experience in your life post-retirement? 

DIAMOND: I don’t want to do anything that has to do with money. Nothing. You don’t bring out the best of yourself. I want to do things that are creative. The art world, I like. I wanna have a good fuckin’ time. I wanna laugh, I wanna drink, I wanna be with people. Happy people, not assholes. We got too many assholes. New York not so much, but in America, we got that scumbag in the White House. When he’s gone, the world will be a better place.

HUNT: Maybe you deserve it, the good time.

DIAMOND: We never deserve anything. We work for it. [Throws his napkin to his plate] That’s it. I’m done. You have fun?