Jesse Bradford was originally slated to play Henry. Macaulay Culkin's father wanted his son to star, saying he would pull Macaulay out of Home Alone 2: Lost in New York (1992) if he wasn't cast in this movie. Fox agreed due to Macaulay's bankability.
Richard and Connie are played by Macaulay Culkin's real-life brother, Rory Culkin, and sister, Quinn Culkin.
The original director, Michael Lehmann, was replaced due to clashes with Macaulay Culkin's father.
The film was not released theatrically in the UK because of the James Bulger case. It was released on video in 1995, with an 18 certificate. The scene in which Henry deliberately drops a mannequin over an overpass was edited because the BBFC feared that children would try to imitate the stunt. The 2002 DVD was passed uncut with an 18 certificate.
In 1988, Michael Klesic was cast as Henry Evans. The film was soon after put on hold due to a lack of funding. A few years later, the original child actors had grown too old for their roles, and Jesse Bradford was cast as Henry. The project was shelved again and again, and the actors outgrew their characters. The project was re-cast again, and finally shot and released in 1993.
The cigarette that Mark and Henry smoke was an empty tube filled with dried parsley and lettuce leaves.
One Halloween, some pranksters near Detroit imitated the scene in which Henry and Mark throw a dummy off of an overpass. A pregnant woman swerved on the road to avoid hitting what she thought was a person, and died.
Mary Steenburgen was originally cast as Susan, but dropped out when the movie was delayed.
The name Henry actually means "ruler of the home". This is very fitting for the film's antagonist, as Henry is very controlling and manipulative of his family.
Despite the fact that Macaulay Culkin taunts and threatens Elijah Wood for much of the movie, he and Elijah Wood became very close friends during production and remain such to the present day.