The tow truck driver hits a lawn jockey after reaching his house. Knocking over lawn jockey's later became a running joke in Home Alone and Home Alone 2: Lost in New York also directed by Chris Columbus.
One of the movie's producers is Debra Hill, who teamed up with John Carpenter to make Halloween (1978), a horror movie about a stalker who murders babysitters. Listen carefully when Sara and Chris watch television. The music you can hear is John Carpenter's chilling Halloween (1978) theme, an in-joke.
The two rival gangs on the El Train challenge each other to a fight when the train crosses "Devereux" street, an in-joke towards director Chris Columbus' wife Monica Devereux and father in law Clarke Devereux who both appear in the movie.
An early draft of the script has the part of Dawson, the garage owner, played by an extremely unfeminine woman and the scene emphasizes the humor of Sara and Brad's confusion over Dawson's gender. This part ultimately went to Vincent D'Onofrio and the scene as it appears in the film plays with Sara's fascination with the comic book hero Thor and has her confusing Dawson with her comic book hero (to Sara he's cleverly disguised as an everyday garage mechanic).
Right before shooting a scene in which the group runs through a dirty, trash-filled alley, the Toronto Sanitation department came by and cleaned it up, so the crew had to dig through local dumpsters for more trash.
Steven Spielberg considered being the executive producer of this film and have the film released under the Amblin banner, to help his friend Chris Columbus get the directing job. However Columbus had the directing job secured.
Both Maia Brewton and Elisabeth Shue starred in Back to the Future movies. In the original Back to the Future, Brewton played Sally Baines, Lorraine's younger sister. Shue played Jennifer, Marty's girlfriend, in Back to the Future II and III.
Sara's love of Marvel comics mirrors director Chris Columbus's who wanted to be a comic book artist for Marvel at one point but decided against it because it's an isolating existence and he preferred to work with people.
When the kids are at the chop shop, Bleak refers to them as the Brady Bunch. In the following scene, when Brenda is still at the bus station, on one of the portable TVs, the theme music from The Brady Bunch (1969) can be heard.
This film was Chris Columbus's first time working with major lighting, cameras and cinematographers. His first day on the set was extremely intimidating and frightening. But after a couple of hours, he eased into it, felt very secure and comfortable and realized this is where he wanted to be.
In the film, Chris Parker is a 17-year-old high school student, and four years younger than Dan Lynch, who is a 21-year-old college student. When the film was released, Elisabeth Shue was 23 years old, and one year older than George Newbern, who was 22 years old.
The project started in the 1960s, with Jane Fonda in mind for the lead role. It was abandoned in the 1970s, then Chris Columbus restarted it in the 1980s. Jane Fonda was too old for the role by then, so it went to Bridget Fonda, who withdrew from the project before auditions began.
According to a recent documentary about Jon Mikl Thor he was originally cast in the part of Dawson. As Thor's gimmick was playing Thor the god (similar to the Marvel comic), the casting would have fit well with the movie's plot points. Thor even was involved with the pre production of the movie and participated in costume fittings. Thor was fired and the part was recast as Vincent D'Onofrio with little explanation given to Thor's agent, though it could have involved D'Onofrio's recent success in the movie Full Metal Jacket (1987).
When the kids are driving through the alleyway with the car thief, the exterior setting was the same setting used in The Fly (1986), which starred Jeff Goldblum and Geena Davis, and which was also filmed in Toronto. The setting was used for the exterior shots of Seth Brundle's apartment/laboratory.
An early draft of the script has no mention of Sara's fascination with Thor. What is included instead is a scene at Soldier Field with The Chicago Bears Players stars Jim McMahon, Walter Payton, William Perry, and Mike Singletary, who invite the team members to come to the Anderson House to watch The Mummy's Curse (1944). When they finally leave, Daryl smuggles out several of the team's jockstraps as souvenirs. The jockstraps later are used to make up the shortage of cash needed to get the station wagon out of (Miss) Dawson's garage. None of the Chicago Bears appear in the film, and the girl at the frat party mentions them briefly.
Filming began on 5 January 1987 in Toronto. After six weeks there, the production moved to Chicago, IL, and later shot some special effects sequences in Los Angeles. To make certain locations double for Chicago, production designer Todd Hallowell added garbage to the streets of Toronto; however, since Toronto's garbage collecting system was so efficient, certain crew members were made to guard the trash from being removed by city workers. Hallowell also headed up the reconstruction of Chicago's Associates Center in Toronto, recreating two of the building's forty stories and replicating the Chicago skyline with a "20 X 40" Translight backdrop. For the scene in which Sara dangles from the side of the Associates Center, a harness and pulley system was used to simulate the "illusion of Maia Brewton being suspended 40 stories up in the air" when the actress was no more than twelve feet from the ground. Other scenes filmed in Toronto included the fraternity party and bus station sequences. In Chicago, locations included: the L Train, where the Chicago Transit Authority shut down a track for several nights; Fitzgerald's nightclub; Lower Wacker Drive; the Chicago Expressway; and a lookout spot with a panoramic view of the city called "Wolfepoint Landing."
In 2016 the name of the "Diamond Building" seen in the movie was changed to the Crain Communications Building. Before that it was called the Smurfit-Stone Building, the Stone Container Building and the Associates Center. (Chicago IL)
When Chris is talking with Brad and Sara in their living room, scenes from the movie Halloween can be seen on their television. As you have previously read, Debrah Hill is the producer of this film and Halloween as well.
In the end of both the 1987 original and 2016 remake films, the babysitter's new love interest returns to see her, but for different reasons. In the 2016 remake, he returns to ask her out on a date and she accepts. In the 1987 original film, he returns because he needs a babysitter; at first she declines, but when she finds out that the babysitter was for him, she accepts.