There aren’t many Frank Gehry buildings in New York, but the architect’s deconstructivist, sculptural designs are so recognizable, you’ll know when you’ve spotted one. There’s the IAC Building, a sail-like Chelsea office tower, possessing the distinctive curves that marked his first real foothold in the elusive city. And there’s 8 Spruce Street, his first skyscraper: A shimmering, folded tower that reshaped the Lower Manhattan skyline. Lastly, but not at all insignificantly (as the project was his first breakthrough in the city), there’s the Condé Nast Cafeteria in Times Square.

Below, AD digs into the three buildings in New York by Pritzker Prize–winning architect Frank Gehry, who forever remains a seminal figure in contemporary architecture.

Gehry’s history in New York

For years New York City represented “the unattainable, the mountain that [Gehry] would try repeatedly to climb, only to find himself sliding back down,” biographer Paul Goldberg wrote in his book Building Art: The Life and Work of Frank Gehry.

Buildings in New York by Gehry are rare because plan after plan fell apart for decades—including a proposed twisted high-rise for the New York Times headquarters and a ribboned, titanium design for the East River Guggenheim. It was only when he was offered the opportunity to design a cafeteria for media company Condé Nast (which owns AD) in Times Square that Gehry finally realized his first project in the Big Apple. Still, it would be years before he finally designed a building of his own in Manhattan. The scarcity of Gehry’s work in New York has made these principal buildings all the more critical to the fabric of contemporary architecture and to Gehry’s mark on the Big Apple.

IAC BuildingIAC global headquarters building

The IAC Building is located in the Chelsea Neighborhood.

Photo: Barry Winiker/Getty Images

Completed in 2007 at 555 West 18th Street, on the corner of Eleventh Avenue in Chelsea, the IAC Building was Gehry’s first full office project in New York City and the first building of his to be constructed entirely of glass. Designed for media company IAC, the 10-story building was shaped to evoke the billowing sails of a ship. Its full-height glass windows transition from clear to white at the cusp of each floor, creating milkier glass above and below eye level when you look out from within.

The building’s design went through numerous iterations (51 different models during early phases, to be exact), and some of the decisions were a product of circumstance: “We hadn’t even decided what color it should be,” Gehry told Vanity Fair. “The earliest models just happened to be white, and Barry [Diller] decided he liked it and that was that.”