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.

Henry wears two different colored shoes - one black Nike and one white.

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.

The sight on Henry's crossbow is a hood ornament from a Buick Riviera.

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.

The movie is partly inspired by The Bad Seed.

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.

Two actors in this film appear in Stephen King adapted films. Daniel Hugh Kelly appeared in Cujo (1983). David Morse appeared in The Langoliers (1995) and The Green Mile (1999).

Both Macaulay Culkin and Elijah Wood were trained by stunt coordinator Jack Gill and rehearsed for six weeks prior to shooting of the climactic scene so that they could be comfortable and act while hanging from a cliff 180 feet above water. When Henry (Culkin) was dropped by his mother (Wendy Crewson), a shot of Culkin himself and not a stunt double falling away from the camera on the actual cliff was required. After discussions with Culkin and his parents, he agreed to do a 30-foot fall on a cable on the actual cliff, 180 feet above the freezing lake, but he wanted one thing in return for this act of bravery: a BB gun. Culkin performed the cable fall perfectly and was given his BB gun.

The fight on the cliff between Macaulay Culkin and Elijah Wood at the end of the film was filmed on a cliff called Palisade Head in Silver Bay, Minnesota overlooking Lake Superior. In the story, it was supposed to be The Atlantic Ocean but a suitable rock face overlook could not be found, and after numerous weekend scouts all over the country, Silver Bay, Minnesota was chosen. For the angles looking down at the water, numerous power boats were used to churn up the water right before cameras were rolled to simulate the ocean waves. The cliff was 180 feet above the water, but the top ten feet of the cliff was manufactured. It was created on top of the actual cliff out of wood and plaster and coated with a rubber material so that the actors could roll around on it and fight as needed. The stunt riggers were hidden inside the fake cliff, controlling safety cables connected to the actors when they were hanging off the side of the cliff and then Culkin's character is dropped.

Henry doesn't kill anyone on-screen.

This is the second Macaulay Culkin film in which his character dies, somewhat high for a child star.

This is the only film where Macaulay Culkin plays a villain.