Jack Lucas' (Jeff Bridges) apartment building – 146 W 57th Street, New York, New York. The 68-story glass skyscraper, known as the Metropolitan Tower (on the left), is located next to the Carnegie Hall Tower (on the right.)
"Video Spot" where Jack now works and lives in the upstairs apartment of his boss and lover Anne (Mercedes Ruehl) – 15 Ann Street, New York, New York.
Jack gets a wooden Pinocchio doll from a little boy – Plaza Hotel, 768 5th Avenue, New York, New York. Synonymous with class and elegance, the Plaza Hotel stands grandly before the southeast entrance to Central Park. In business for over 100 years, the hotel finds its way in film after film: North by Northwest, Barefoot in the Park, Arthur, "Crocodile" Dundee, King of New York, Metropolitan, Home Alone 2: Lost in New York, and American Hustle just to name a few.
Jack ponders about the meaning of life – General Sherman Statue, Grand Army Plaza, New York, New York. It was the last sculpture created by Augustus Saint-Gaudens. Over the years the statue's original gold-leaf cover peeled away. In 1989, through the efforts of the Central Park Conservancy, the monument was returned to its gilded glory. After some public debate, the shiny surface was toned down with pigmented wax. There was again significant loss of gold leaf in recent years, and in 2012 the Central Park Conservancy embarked on another restoration campaign.
Jack is attacked by two punks but is saved by the eccentric Parry (Robin Williams) – Main Street Park near the Manhattan Bridge, Brooklyn, New York, New York. The area now looks much less derelict than in the film. In addition to the popular Pebble Beach and nautical-themed playground, the park features an expanded lawn, a dog run, and Main Street Terrace.
The homeless camp – Manhattan Bridge, Adams Street at Plymouth, Brooklyn, New York, New York.
Jack is looking for Parry – Manhattan Bridge near Water Street, Brooklyn, New York, New York.
Jack sees Parry sitting on top of a car – Park Avenue South at E 24th Street, New York, New York. The Metropolitan Life North Building is a 30-story art deco skyscraper with the main entrance at 11-25 Madison Avenue. The building is bordered by East 24th Street, Madison Avenue, East 25th Street and Park Avenue South, and is connected by an elevated walkway to the Met Life Tower just south of it.
Jack crossing the street – E 24th Street at Park Avenue South, New York, New York.
Lydia's (Amanda Plummer) office – 330 Park Avenue South, New York, New York.
Parry and Jack watching Lydia as she buys a paperback – E 42nd Street at Park Avenue, New York, New York.
Lydia having lunch at a Chinese restaurant – 294 5th Avenue, New York, New York. The restaurant has since closed.
Parry shows Jack "the castle" where the Holy Grail is supposedly kept – Madison Avenue Facade of the Squadron A Armory, Madison Avenue at E 94th Street, New York, New York. It was designed by John R. Thomas for Cavalry Squadron A in 1894-95. In the early 1960s the building was targeted as the site of a school and subsidized housing. Although the project was subsequently abandoned, the armory building was given to the Board of Education for use as the Intermediate School 29 (now Hunter College High School and Elementary School.) Late in 1968, after significant portions of the armory had already been torn down to make way for a new building to be designed by Morris Ketchum Jr. & Associates, public protest succeeded in halting the demolition and drawing the attention of the Landmarks Preservation Commission, which designated the remaining western facade on Madison Avenue a historical landmark. Ketchum, who would later serve as a member of the Landmarks Preservation Commission (1972-79), designed a fortresslike building for Intermediate School 29 retaining the facade of the former armory as a dramatic backdrop for the school's playground.
Parry is meditating on a rock – the southeast corner of Central Park, New York, New York.
Parry and Jack help a homeless cabaret singer (Michael Jeter) – Eaglevale Arch: W77, Central Park, New York, New York. According to Gilliam, Jeter's drag outfit was inspired by Marlene Dietrich in Destry Rides Again.
Jack and Parry wait for Lydia at Grand Central Terminal – 89 E 42nd Street, New York, New York. The now famous waltzing sequence was not in the original script. Gilliam came up with this idea when he was scouting the location.
Parry teaches Jack "cloud-busting" – Sheep Meadow, Central Park, New York, New York.
Parry, Lydia, Jack and Anne going out – Gold Street near the Brooklyn Bridge, New York, New York.
Lydia’s apartment – 157 W 80th Street, New York, New York.
The Red Knight appears before Parry – W 80th Street, New York, New York.
Jack and his agent Lou (David Hyde Pierce) go for a TV show pitch – 101 Park Avenue, New York, New York.