In City of Dreadful Night, four characters–Gus, in his thirties; his brother, Tony, in his thirties, Philly, in his twenties; and Anna, in her late twenties–enact the discovery of an unsuspected murder. The scene is New York City in the late 1940s and a unit set represents all locations simultaneously: a park bench DR, a coffee shop with curved counter and stools DL, a bedroom with bed and chair on a platform UC, and the street played across the downstage area. We hear the sound of pigeons in the dark and lights come up on Gus and Tony on the park bench as Anna, in the upstage shadows, sits before her mirror, and Philly leans on the counter of the coffee shop reading a newspaper. From the laconic conversation of Gus and Tony we learn that Gus wants Tony to spy on Anna. Gus thinks Anna is seeing someone and he wants Tony to find out who the man is. Tony suggests that perhaps Gus should forget about Anna but agrees to follow her. As Tony moves downstage, Anna asks him if he is following her. Anna thinks she recognizes him and suggests that he would like a piece of warm cherry pie. Tony says he might have liked one before the war but he isn’t sure now. Anna says that perhaps he can have some when he gets done following her. As Anna sits on the bench with Gus, Tony sits on a stool in the coffee shop. He asks Philly if he recognizes the picture of Anna that Gus gave him. Philly warns Tony to watch out for her, that she is trouble. He tells Tony that he has seen her with a man he thinks is a killer. Tony writes a phone number on a napkin and tells Philly to call him if the girl comes in again. Tony goes to Anna who is sitting on the bench feeding the pigeons. She tells him she saw him looking up at her window the previous night and says that Gus is paying him to follow her. Tony denies being paid anything, and, as Gus moves into Anna’s room and sits before the mirror, she remembers seeing a photograph of Gus and Tony and a pretty girl taken at Coney Island before the war. Tony says that when he sees her moving from window to window in her red slip she reminds him of a girl he used to know. Anna asks Tony who got the girl in the photograph but he says he can’t remember. Anna asks him to come up to her room, and when Tony says he’s busy she says she’ll leave her door unlocked if he wants to come up later. She goes to her room where Gus has been waiting. He asks her where she has been and gets upset with her evasive answers. She asks him where he goes at night and tells him that if what he does is none of her business then what she does is none of his. Gus leaves and joins Tony on the bench, asking him if he has found out if Anna is seeing somebody. Tony tells him that sometimes Anna walks to see the monkeys in the zoo and sometimes goes to Coney Island. We hear the sound of seagulls and lapping water as Tony joins Anna looking out at the water on Coney Island. Anna says there’s somebody else inside Tony, someone a lot more complicated. She thinks Tony wants her and wonders what Gus would do if he caught them naked in bed together. She says the gulls and the smell of the water remind her of Cape Cod and doing everything with her sister until the war came and her father left and her mother went insane and her sister went away. She walks into the upstage shadows and Tony moves to the coffee shop. Philly says the woman Tony was asking about came into the coffee shop with some guy, a guy that looked like Tony, a few nights earlier. Tony gives Philly a dime so that he can call him the next time the woman comes in. Tony leaves the coffee shop and paces back and forth across from Anna’s place, talking disjointedly to himself, seeming to be almost remembering something. As he looks up at Anna’s window, the light fades on him, ending the first act.
Act Two begins as the lights come up on the bedroom with Anna just opening the door for Tony. Philly is behind the counter in the coffee shop and Gus sits on a stool drinking coffee. Tony tells Anna he needs to talk to her and she asks him to come in. She is trying to remember a nightmare about her mother and sister, but Tony says that Gus will kill her if she is cheating on him. She taunts Tony until he slaps her and she falls backwards across the bed. She asks Tony if he wants her and wonders if he hit the girl in the picture at Coney Island. When Tony says he is trying to save her, Anna asks what Gus has on him. Tony says that his head got hurt in the war and that Gus looks out for him by helping him remember things. Anna says that Gus doesn’t want him to remember and asks about the girl in the picture. When Tony says that he thinks she died, Anna asks if he killed her, if Gus helped him get rid of the body. Tony says that she loved Gus and when Anna says that Tony killed her, he grabs her around the throat and says loudly that he didn’t kill her. When he lets her go, he sits on the bed, and Anna asks him who she looks like. He says she looks like Ida Lupino and like the girl in the picture. In a long speech, Anna explains that the girl in the photograph was her sister who ran off to live in the city, leaving Anna to take care of their sick, drunk, half-crazy mother. The sister wrote letters every week but then the letters stopped. The mother fell down the stairs and died and Anna came to the city to look for her sister who had disappeared. From the photographs her sister had sent, Anna was able to locate the coffee shop and, one day, Gus. Then Tony started following her and now she wants to know which one of them killed her sister. The lights come up on the coffee shop where Philly is telling Gus about Tony following Anna. Gus says he told Tony to follow her but is surprised when Philly tells him that Tony has been in Anna’s room. Gus leaves the coffee shop and the lights come up on Tony and Anna in her room. She wants to know who took the pictures of Gus, Tony, and her sister. Tony seems about to remember when Gus comes in, asking what’s going on. Anna tells Gus that he knew her sister and shows him the Coney Island photo. Gus thinks she has taken it from his room but she insists her sister gave her a copy of the picture. Tony remembers that the name of the girl in the picture is Faith. Gus notices the mark on Anna’s face where Tony hit her and says he will kill him if he touches her again. He accuses Anna of being with him just to find out what happened to her sister. Gus says he hasn’t seen the girl since before the war and when Anna asks about the picture in his room Gus says it is a picture of his brother, Tony. He is bothered that Anna pretended to like him even though she thought he might have killed her sister. When Anna tries to leave, Gus throws her on the bed, saying she is not going anywhere, that he needs to think. Tony asks Gus who took the pictures of the three of them and the lights fade on the bedroom and come up on the coffee shop where Philly is reading the paper. Tony enters from out of the darkness. Philly serves him black coffee and asks if he wants a piece of cherry pie. When Anna enters, Philly gives her coffee with extra sugar and lots and lots of cream. Gus comes in and says he has a job to do. He asks Philly where his camera is but Philly says he doesn’t have a camera any more and that he spent the war in prison because he did some stupid things because of mental problems. Tony remembers that Philly was the kid that used to follow them around before the war, and Gus wants to know what happened to the girl. Under pressure from Gus, Philly admits that he took the girl to Coney Island and thinks that she may have gone to see her sister. Philly says that Anna can’t be the girl’s sister because the girl told him her sister had dangerous mental problems and might have killed their mother and that was why she was going back home to Cape Cod to talk to her. Tony says he remembers getting a letter from the girl just before he went overseas, verifying what Philly says. Gus asks Anna what she has been doing since the war started and Anna admits that she had a nervous breakdown after her mother died and that she was put in a place where they gave her drugs and shock treatments. She tells the men of a bad dream she keeps having about walking on the beach with her sister and being angry with her for suggesting that she pushed their mother down the stairs. Anna says that in the dream she picks up a rock and hits her sister in the head and her sister falls face down in the water. Anna runs away but when she comes back her sister is not there. Anna says the dream keeps playing in her head over and over but that it’s just a movie. She asks Philly for some pie and Gus wants to leave. Tony says he’ll stay for a bit and tells Philly to give Anna some pie. Anna eats a piece of pie and says it’s very good. The lights fade and go out.