Thomas Webb (Callum Turner) is the son of a publisher (Pierce Brosnan) and his artistic wife, who has just graduated from college and is trying to find his place in the world. Moving from his parents’ Upper West Side apartment to the Lower East Side, he befriends his neighbour W.F. Gerald (Jeff Bridges), a shambling alcoholic writer who dispenses worldly wisdom alongside healthy shots of whiskey. Thomas’ world begins to shift when he discovers that his long-married father is having an affair with a seductive younger woman (Kate Beckinsale). Determined to break up the relationship, Thomas ends up sleeping with his father’s mistress, launching a chain of events that will change everything he thinks he knows about himself and his family.

34 West 74th Street (btw Central Park West and Columbus Avenue) Manhattan.

otsoNY Comments: Production Designer David Gropman and Location Manager Kip Myers searched all over New York to find the locations that retained the city's "edgy, ungentrified side." They insisted that each scene would be shot in its appropriate neighbourhood as stated in the film.

Thomas's Apartment, 151 Ludlow Street (btw Rivington & Stanton Streets) Manhattan.

otsoNY Comments: The title of this film is taken from a Simon & Garfunkel song, and it was actually shot on 35mm as opposed to digital.

The Box Nightclub, 189 Chrystie Street (Btw Rivington & Stanton Streets) Manhattan.

Grand Central Restaurant, 89 East 42nd Street and Park Avenue, Manhattan.

Park Avenue and East 40th Street, Manhattan.

Bryant Park, West 40th Street (btw 5th and 6th Avenues) Manhattan.

Office, 32 West 40th Street (btw 5th and 6th Avenues) Manhattan.

West 42nd Street (btw 5th and 6th Avenues) Manhattan.

Subway, West 42nd Street and 6th Avenue, Manhattan.

Cafe Select, 212 Lafayette Street (btw Kenmare & Spring Streets) Manhattan.

Washington Square Park, Greenwich Village, Manhattan.

Johanna's Apartment, 45 Mercer Street and Broome Street, Manhattan.

Mercer Street (btw Prince Street and West Houston Street) Manhattan.

La Esquina, 114 Kenmare Street and Lafayette Street, Manhattan.

otosNY Comments: Special thanks to Bob Egan for finding this location.

YG Studios, 33 West 17th Street (btw 5th & 6th Avenues) Manhattan.

otsoNY Comments: Argosy Bookstore at 116 East 59th Street doubles for the fictional bookshop The Pale Fire. The Argosy is New York City’s oldest independent bookstore, and occupies an entire six-story townhouse with various sales floors specialising in first editions, Americana, leather bindings, antique maps and prints, and autographs. The store, also noted for a wide selection of bargain books, has its own framing and shipping departments and owns a large warehouse in Brooklyn.

Bookshop, 116 East 59th Street (btw Park Avanue and Lexington Avenue) Manhattan.

otsoNY Comments: The brooklyn Museum has appeared in several films including The Rebound, The Chosen, The Hot Rock and New Year's Eve. At 560,000 square feet, the museum is New York City's third largest in physical size and holds an art collection with roughly 1.5 million works.

Brooklyn Museum, 200 Eastern Parkway and Washington Avenue, Brooklyn.

Mercer Street and Prince Street, Manhattan.

Lure Fishbar, 142 Mercer Street and Prince Street, Manhattan.

Jane Hotel, 113 Jane Street and West Street, Manhattan.

Car Park, West 18th Street (btw 5th and 6th Avenues) Manhattan.

The Brooklyn Inn, 148 Hoyt Street and Bergen Street, Brooklyn.

The Mall, Central Park, Manhattan.