Some artistic directors determine the seasonal programming for a theater, opera house or community space. Zack Winokur, however, has an island unto himself.
For the last three seasons, Winokur has served as the producing artistic director of Little Island, the artificial island/public park adjacent to Manhattan’s Meatpacking District in the Hudson River which opened five years ago.
While the Juilliard-educated Winokur had directed, produced and/or cocreated theatrical and opera productions prior to this gig (he also co-founded the imaginative American Modern Opera Company in 2017 and serves as its artistic director), Little Island at Pier 55 is unlike any other performance space in a city that has no shortage of them. Not only is it outdoors, but, as the name suggests, it’s a literal island. Unlike, say, theatrical performances in Central Park, Little Island presents artists and innovators with the opportunity to shape the audio-visual experience of an entire discrete outdoor space.
This season, Little Island features new works from returning musical iconoclasts (Justin Vivian Bond opens the season with Summer’s Eve from July 29-31; Anthony Roth Costanzo takes a tour through minimalist music history from Aug. 5-9; Laurie Anderson participates in Thomas Bartlett’s Allen Ginsberg at 100 from Sept. 2-6) as well as excavations of New York City’s rich musical foundations (The Late Show with Stephen Colbert bandleader Louis Cato brings the music of the Savoy and Harlem Renaissance back to raucous life from Aug. 19-23; three-time Grammy winner Cécile McLorin Salvant explores the edges of Tin Pan Alley from Aug. 12-16).
Additionally, creative trailblazers are bringing their distinct visions to the island. Tony winner Qween Jean throws a Summer Legacy Ball extravaganza on Aug. 1, and from Aug. 27-30, Julio Torres and Martine Gutierrez premiere Marina, “an underwater fairytale about love, belonging and catfishing” (what else would you expect from the boundary-free brain of Torres?) commissioned by the 2026 Whitney Biennial.
Throughout the entire season, Papi Juice parties — thrown by the Brooklyn DJ/art collective centered around uplifting queer and trans people of color — will bring free dance parties to the island’s “Play Ground.” The Papi Juice parties always dovetail with one of the performances at The Amph, Little Island’s 700-plus-seat amphitheater – meaning you can catch a show, grab a drink and shake your thing all on the same night on the same island.
Ahead of Little Island’s 2026 season, Billboard spoke with Winokur about how he approaches programming the bespoke space, what we can expect from this year’s slate and why certain Little Island performances remind him of MTV Unplugged or “the parade of animals going to the Big Apple Circus.”
To begin with, how did you end up landing this role?
It actually is a weird, circuitous route. Before the park was built, I was starting my own company, the American Modern Opera Company, AMOC, and we were in conversations to do a show well before the park was built. That never happened. And then when it opened in the first summer, Mikki Shepard ran this really beautiful free festival that was super dense — I think it was just one month, but just gigantic. And my company did a show of all Julius Eastman’s music that was the closing night of the opening festival. Then Barry Diller [billionaire businessperson who commissioned Little Island] called me and asked me to think about a new approach to programming, and we came up with this thought of doing more original programming. I started my first season in 2024.
Was there a thesis when you were talking to Barry? Was there a unifying idea to the kind of things you were looking for?
I think the thing that we were most excited about, and certainly I was most excited about, was a couple of things. One is that we so rarely think of performance as part of public art, and the idea of doing shows in a public park feels incredibly special. So one of the points was to bring a real high-low sensibility to a public space and to make it as accessible as possible, which is why so much of our programming is free and the maximum ticket price is $25. And I was always really interested in extraordinary people, and people particularly who live here or are inflected by the city in one way or another. I think so many of the things that we’re doing this year, and that we’ve reflected on in the past, are about different scenes or icons from the past, the present and the future, all colliding in one place on the island. If that makes sense.
It does. In terms of audience, who is Little Island programming for?
I think it reflects who visits the park, actually, which is always a very interesting thing. In the summers we have days that are 13,000 people just visiting the park without performances happening. What’s interesting about it is that it has quickly become an iconic place in the city, and therefore it’s a very popular destination for tourists. But it’s also a neighborhood park. You see the same people running through it, the same families coming through every morning. That was the thing I’m thinking about all the time in terms of the programming as well — that it should be attractive to anybody, and it should feel like a space that is extremely for New Yorkers without being exclusive at all.
How do you figure out the season? Are you looking at performers around the city and thinking, “I like what they’ve done in the past, so let’s talk with them about what they might have coming up”?
It’s a mixture of things. I’m always on the lookout for people who surprise me. I’m also always interested in asking people who I just think are extraordinary to do something a little bit further to the edge of what they normally do — and also putting back into the center things that are on the edges. So I think about this sense of the neighborhood and its icons — thinking about past seasons with the likes of Twyla Tharp and Qween Jean, who’s returning, and Charles Ludlam and Justin Vivian Bond, who is a scene all to herself, and even Meshell Ndegeocello taking on Baldwin [in 2025]. These are all people exploring moments that defined New York, and that also might define the future of our city. Even things like this season — we have Florent coming to the island, who had this extremely famous diner in the Meatpacking District [from 1985-2008]. So also things that are also hyper, hyper local.
Nina Westervelt/Courtesy DKC/O&MYou brought up Viv. You were one of the co-creators of Only an Octave Apart, a show that turned into an album I absolutely adore. With someone like Justin Vivian Bond or Anthony Roth Costanzo, who have been at Little Island every season with you so far, do you just call them up and say, “Got any ideas?”
I think with Anthony in particular — people who I’ve worked with for so long — it is a pretty organic conversation. The first project with Anthony was kind of a hilarious accident that came out of our work in Only an Octave Apart, where he does the male and female parts of this Figaro duet. By the 50-something-odd performance, we were in Dublin, and he was doing the show, and afterward I was joking with him. It started as a bit and then it just got really good. I said, “Maybe one day we should do all of Figaro — where you sing every role.”
Then I was working on a show for my first season that dropped out because someone got a really fabulous arena tour, and I called Anthony and said, “What if we actually did it?” We spent a couple of days trying to figure out whether there was a way to edit it down so that he could actually survive, and then we just endeavored to pull it off. That was extremely fun.
Similarly, thinking about him in the context of Maria Callas with Charles Ludlam [Galas] last year. And for this year, because we really are focusing on music, I was interested in — obviously he’s had a very big moment with minimalism, particularly with the music of Philip Glass, with Akhnaten and also Satyagraha with another person I work very closely with, Bobbi Jene Smith, who’s also been on the Island, who directed the Satyagraha in Paris. So he’s doing the entire trilogy.
I was wondering if we could think of a kind of maximalist version of minimalism — his version of not just Philip Glass, but also of [Julius] Eastman and John Adams and Meredith Monk. Could we bring in Moondog, could we bring in Steve Reich, and who were all the other people? He’s really been, as always, just a fabulous thought partner in reaching toward these unexpected edges of the genre that he, in this moment, is coming to define in some way.
With Viv, it’s always an unbelievable adventure, because she’s completely uncontainable in the most fabulous way ever, and always comes up with something that no one else would ever do. This year it came from kind of a joke, where she was like, “I’ve always wanted to do a show where everyone is on fainting couches.” So we engaged the fabulous Adam Charlap Hyman and his firm, Charlap Hyman & Herrero, to help us think about what those fainting couches would be for all of the musicians as well as Viv. Dries Van Noten is now doing the wardrobe for the band and for Viv, and she will start out lying down.
She’s pre-fainted.
She was like, “If I’m going to perform in August outside, I’m pretty sure I need to be drinking water and lying down.”
Really, though. Climate change is doing its thing, and the last few years in New York have been really been brutal with these heat waves. How challenging is that for programming?
Yeah, it’s just affected life. It’s really tough. We do our best to just put on the show, no matter what. There are certain things that we just can’t do because it’s unsafe — with lightning or whatever. But thankfully, we’re at night, so by evening it usually is a tolerable heat. And one of the things I feel like people don’t always know is that, in addition to delicious lemonade and water, there are also cocktails available and a liquor license across the entire island, so you can always be drinking, which I think helps mediate any weather issues at all.
It’s just one of those things that I think is so special about this venue. It certainly makes it difficult that it’s uncovered and outdoors. However, when it is a gorgeous night, which it often is, there is simply nothing better than being able to have a cocktail, watch an unbelievable show, look at the Hudson River under the stars, and then to walk out on any of these Friday nights in our season and stumble into a Papi Juice party. That’s a thing that can only happen on Little Island and only happen in New York.
The Marriage of Figaro, which you talked about, was one of the best things I’ve seen in the city. It was so much fun, so bonkers, so impressive. Having done this a few years now, what have you learned about the space that you use as you approach future programming?
Well, one of the things I’ve always loved about this space is that it’s a thrust stage, so it’s actually really intimate, even though it’s over 700 seats. You’re never that far away from any performer, and that intimacy is something we’ve always tried to find the happy medium of. Figaro is a great example of something that felt really grand, like a great spectacle, but also homespun and very nuanced. To have an orchestra that’s only eight players playing that music, and the sound system is so extraordinary that you really feel like — in a weird way — this is what opera was meant to be. Or how opera was meant to be experienced, rather than in a gigantic space.
Then I think about these other moments — Jeremy Denk and Conor Hanick playing Ives, or Meshell Ndegeocello — moments that harken back for me to an MTV Unplugged moment, where just these unbelievable superstar people are so close, and also not on a proscenium, just out in the middle of this island. That feeling is where it feels most like a neighborhood park — like this is a public living room, and that is incredibly special.
I’ve also always loved the fact that it’s wonderful that every show has always been sold out, and that even when things are packed and the standing rail is packed, if you are a tourist or a local who’s just walking in the neighborhood and didn’t expect to see a show, you still can get one. We’ve linked all of the speaker systems throughout the park so that the music happening in The Glade or in The Amph can be heard in the Play Ground. You have these beautiful vantage points from all of the pathways, so if you don’t have a ticket, you can still see and experience the show in a really fabulous way. I don’t think there is another theater that just doesn’t have walls. What that symbol means in the city, to me, is one of the greatest gifts that’s ever happened.
In terms of the actual Amph space, before a show opens, how many times do they get to run through it?
It totally depends on what it needs. It’s always a little bit of a game of Tetris, because the season is only so long and there are only so many shows, and we want to have as many public performances as possible. In the past, it’s always been really interesting to me. I remember my first season we opened with this new Twyla Tharp piece, and there were weeks of tech rehearsal — and of course the tech rehearsal is happening in the theater in the public park. So tech rehearsal was watched every single night. I couldn’t believe it.
As a real theater nerd and a director myself, I love tech. It’s not something I’ve ever thought many other people would enjoy watching. But to have hundreds of people watching Twyla Tharp run up and down the aisle to give notes to dancers actually felt like it was lifting the curtain on something people never get to see. It became this very special kind of New York moment — like the moment where you get to see the parade of animals going to the Big Apple Circus down the avenue. Just something that is so improbable.
We give people the time they need. I think every person who does this would say that there’s never enough time for anything, but we give people the time that they need depending on what the project is. And thankfully the sound system is surprisingly wonderful, so it’s usually pretty quick to get it sounding great.
How much involvement do you have with each production? Does that really depend on what the production is — how much they invite collaboration?
I’m a very hands-on producer. Particularly on past commissions, like Figaro or Twyla, it’s incredibly involved and hands-on. I think that good creative producing is being a collaborator, not just being an investor. On many of the projects we have this season that are more concert based, it’s just an incredibly delicious tossing around of ideas — being a sounding board and a thought partner to everybody.
Nina Westervelt/Courtesy DCK/O&MThis season, Cécile McLorin Salvant is doing a Tin Pan Alley show, and then there’s one from Louis Cato that’s a Harlem Renaissance show. Both of those call back to 100-plus-year-old New York music history. How are they going to take something that’s an iconic part of history but make it applicable for modern audiences?
I think this music has never not been applicable and never not been listened to, frankly — beyond its obvious influence in so much of what popular culture is today, from every moment since the ’30s. With Cécile — Cécile is just one of the great, great performers and musicians, let alone vocalists, that I’ve ever known. One of the things I find so unbelievable about her is that she’s the queen of the B-sides. She takes these songs that you don’t really think about, and suddenly they become these anthems, and it sounds like she wrote all of it.
I think about Nina Simone in a similar way, where you listen to her sing a Bob Dylan song and you’re like, “She wrote this. There’s no way that he wrote that.” Cécile has a similar force in our world. One of the things that was interesting to me when I asked her to do this was to think about Tin Pan Alley, which has so many hits, and to think about the stranger edges. She just makes things completely her own. So that’s what we can expect — with obviously the greatest band of all time, and her great collaborator Sullivan Fortner on piano.
And with Louis, I’ve been thinking about this a lot recently. There are certainly other moments where there’s big band and swing music in New York, but there are certain composers, like Fletcher Henderson, who are people we don’t always think about. Part of the point for him is to bring some of these people into the light in a different way — people who were super influential in defining these musical styles, but who we might not have given total due to before. I’m thinking also about Arthur Russell last year, who’s an artist that I think is incredibly important and influential, who I’m not sure that many people know about. Giving him a gigantic marathon performance in this public park felt like a big moment. So Louis Cato is really bringing a small big-band energy and exposing different people.
The other thing — I was just reading this really extraordinary new book called Nonstop Bodies by Rennie McDougall. It’s a history of dance in the city, and there’s a whole chapter on the Savoy that really brought it to life for me. The Savoy dance floor was 50 feet by 200 feet. That’s enormous. It was packed constantly, and there was a big band on both sides to make sure that music never stopped for one second. Just those kinds of details — thinking about how lively and how immense those places were and remembering never to minimize them.
Day-to-day, what are you doing during the season? Are you there literally all the time?
It’s definitely not a nine-to-five. We’re in this delicious moment right now where everything’s loaded in, so all of the lights are up and all of the speakers on the catenary system are there, which takes a while to get up. A normal day is moving between meetings with these artists to check how things are going, to be in conversation with them, looking at the order of these concerts, making sure that stage layouts are making sense, making sure that everybody’s backline is in order.
Today I did a couple of site visits with designers and lighting designers, to step onto the stage and make sure we’ve walked through it, looking at what’s possible. I have an unbelievable, incredibly dedicated team. Once we go into production, it’s this wild thing where we are in the office and then we are at all of the shows, making sure that everything is good.
I’m there basically every single night, and it’s one of the treats. If I’m being totally honest, I’ve basically lived here since I was 15, and I had never spent a summer in New York until I got this job — like a full summer. To be able to be on the island with all of the visitors, and have a drink, have a snack, and then take in a free show in the Glade, and then a beautiful show in the amphitheater, and then one of these Papi Juice parties — it’s amazing. It’s just a totally amazing place.
And there’s quite a variety. It’s not a Broadway theater where they have the same show for months, years even. Every few nights you’re switching to something else.
Part of the fun has always been that it’s a season. The fun of making a season is figuring out how things both complement each other and collide with one another and balance each other. One of the things I love is that, especially on Friday, Saturday and Sunday, there are at least two shows a night in the different spaces.
And back to an earlier question about what I’m learning about the space — one of the things that feels really amazing that we learned, I think with Arthur Russell first, was that we could do six hours of uninterrupted music, and we could also transform how people entered the space. There was this whole drone improvisation with Sam Amidon and Laurie Anderson walking around with their instruments throughout the entire park.
Those moments where the whole 2.4-acre park becomes one big idea and one canvas is something we’re exploring more this year and is something you can’t do anywhere else. It would be like a Broadway show getting to control the entire street they’re on. The drinks, the food, what you’re hearing when you step across the highway onto that bridge — being able to design that entire experience is very special.