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.