Yes, yes, I know: What!? 40 Bond but no 40 Mercer? Yes to the Lipstick Building, but no to the LVMH Tower? I share your pain: Despite what people say, we just don’t live in a design-poor city. So I chose work that had major impact, upheld its ideals, and became a part of our lives. I left out most private interiors, and I chose each architect’s greatest, not largest, work. That’s why Renzo Piano’s Morgan Library made the cut and his Times Tower didn’t. And I omitted the new Pritzker winner, Jean Nouvel, because I think his best New York work is yet to come.

(Photo: Ezra Stoller/Esto)

FORD FOUNDATION BUILDING, 1968
Long before green became a cause more than a color, Kevin Roche and John Dinkeloo designed a corporate terrarium that oxygenates the office air. Employees look in, not out, on nature: The best views are of the atrium. It’s a vertical park, and one that East 42nd Street sorely needed. (Technically, it opened in December 1967, but it was the talk of ’68.)

(Photo: Peter Aaron/Esto)

WORLD TRADE CENTER, 1973
Minoru Yamasaki’s Twin Towers seemed to have stepped on the city rather than grown out of it, but in their defiant bulk they did represent New York swagger. Even the holes they left, in the sky and in the ground, triggered a surge of interest in the city’s future shape.

(Photo: Stan Honda/AFP/Getty Images)

CITICORP CENTER, 1977
A pillar of brawn in a silken skin, Hugh Stubbins & Associates’ Citicorp defies a midtown skyline full of flattops with its rakish slanted roof. The tower seems to be hoisting itself into the atmosphere, an impression strengthened by the sunken plaza and the boosterlike columns at the midpoint of each side, at once powerful and dainty.

(Photo: Stan Ries/Courtesy of BPC)

BATTERY PARK CITY, 1979 (MASTER PLAN)
Thirty years after it was planned as a brick-and-nostalgia evocation of the Upper West Side, Battery Park City has rescued the waterfront from a century’s worth of defunct docks. Sailboats launch from an adorable marina, joggers commune with harbor views, and a neighborhood built on landfill has finally, unexpectedly, acquired character.

(Photo: Peter Aaron/Esto)

PAUL RUDOLPH PENTHOUSE, 1977–1997
Perched like an urban tree house on a block stiff with Knickerbocker gentility, Rudolph’s four-level assemblage of modern boxes and lattice-covered balconies foams over the top of a Georgian townhouse. Twenty years of his tinkering added floating planes, stairs without railings, and vertiginous openings to multistory drops; it’s a showcase for the glamorous, childless Manhattan life.

(Photo: Courtesy of Eisenman Robertson Architects)

FIREHOUSE FOR ENGINE CO. 233, LADDER CO. 176, 1985
A Brooklyn cocktail, toughness topped with theory. In Peter Eisenman’s Bed-Stuy firehouse, the first floor is all no-nonsense defiance. Then the silvery upper story sweeps back at 45 degrees to the street, following the line of the nearby el and giving depth to the Mondrian grid.

(Photo: Courtesy of The Noguchi Museum, NY)

THE NOGUCHI MUSEUM, 1985
In one of those undistinguished old factory buildings that litter neighborhoods like Long Island City, the sculptor Isamu Noguchi birthed what would become a posthumous museum to himself. Outside, it looks like nothing, but the concrete floors, exposed I-beams, and rough/polished hunks of stone, bathed in milky daylight, make it a lovely postindustrial oasis.

(Photo: Peter Mauss/Esto)

THE LIPSTICK BUILDING, 1986
Philip Johnson, that wily New York character, could make appalling errors in judgment, but this seemingly retractable tower wasn’t one of them. The oval cylinder sheathed in coral-colored stone, bearing a smaller cylinder and then another, might have been another preening postmodern gewgaw if it were in, say, Houston. On blah Third Avenue, it’s more like a reproach: Lighten up!

(Photo: Jeff Goldberg/Esto for Polshek Partnership Architects)

NEW YORK TIMES PRINTING PLANT, 1997
In the world’s capital of branding, even the Gray Lady plasters her name across its plant, like a giant copy of the Times hanging off the breakfast table. The paper made the switch to color late, but with gusto, installing new presses in Polshek Partnership’s billboard-building just off the Whitestone Expressway. It’s meant to make an impression at 60 miles per hour: Blocks of yellow and red jump out from a newsprint-white façade. No sober impartiality here.

(Photo: Courtesy of Helpern Architects)

CONGO GORILLA FOREST, BRONX ZOO, 1999
What might have been an exercise in zoological kitsch—follow the winding path into a Vegas-ish miniature rain forest, complete with mist—turned instead into a way to commune at close quarters with disturbingly familiar primates. In Helpern Architects’ ape house, spectators and displays both press their cheeks against the glass, but the gorillas are the ones frolicking freely, watching the humans packed together in their dark shed.

(Photo: Courtesy of Roger Dong '2000 and Conde Nast Publications)

CONDÉ NAST CAFETERIA, 2000
In his first New York project, Frank Gehry grappled with a venerable publishing-industry ritual: lunch. The space fails in its literal requirements—getting hungry staff through a line, to a table, and quickly back to their desks. New Yorkers are used to jostling, only here they do it in a radiant space that appears to be in a constant state of liquefaction. By comparison, Gehry’s first freestanding building in the city, the IAC headquarters on West 19th Street, looks fussy and vague.