In this modern parable of middle-American values, a nine-year-old boy leaves behind the family farm for a few very instructive days in New York. A disagreement with his father sends Brill (Richard Bray) hitching to New York City to seek his fortune. After arriving in Manhattan, he falls in with a young gang of shoe-shine boys and paper carriers who are "managed" by Rick (Jaime Charlamagne), a teenage punk who "protects" them in exchange for half their earnings. With the help of his new friend Paco (Roberto Marsach), a Puerto Rican boy about his own age, Brill gets a job selling papers. The next day Brill wins most of Rick's money in a crap game and he takes Paco out for a night on the town. When Rick's gang beats up Brill for winning the money, Suzy (Lee Grant), a prostitute, takes him home to care for him. The next morning, Suzy buys Brill new clothes and takes him on a tour of the city. He sees Suzy picked up by the police and decides to return home, purchasing a bicycle for the trip. Rick's gang spots him and gives chase, but Paco intercepts them, allowing Brill to escape. On the highway home, a truck wrecks the bike, and Brill stays the night at an elderly African-American couple's house. Upon returning home the next day, he presents his father with the remainder of his "fortune."
Pie in the Sky was Allen Baron's second attempt at directing and screenwriting. His 1961 Blast of Silence received good reviews, but never gained popularity in the United States. Pie in the Sky is a better film, painting a realistic yet heartwarming picture of a young boy's adventures. Richard Bray gives a commendable performance as the wayward youth, despite his non-professional status as an actor. The film was criticized for choppy narration in 1964, giving a "too European" feel, although modern audiences would likely be more accepting. Donald Malkame's cinematography is one of the film's strongest points. It is clear, crisp, and shot entirely on location -- including 42nd Avenue through hidden camera, and the exciting bicycle chase through upper Manhattan. ~ Lucinda Ramsey, Rovi