- Creator Killer: The film's problematic shoot and subsequent critical and commercial failure put an end to the directing career of John Hughes, who focused solely on writing and producing for the rest of his life afterwards. And even in those fields he never had another film that was a hit critically, albeit many of them were big box-office successes until Home Alone 3 torpedoed his career entirely.
- Hostility on the Set: According to Kelly Lynch, James Belushi and John Hughes did not get along, and argued constantly. Production was shut down for a while, because Belushi refused to come out of his trailer to the set.
- What Could Have Been:
- Alec Baldwin was originally cast as Bill Dancer, but was unavailable due to his commitment to a Broadway production of A Streetcar Named Desire. John Travolta and Bruce Willis were also considered. Travolta was busy shooting Look Whos Talking Too, and Willis' agent wanted too much money, which was more than the film's budget could afford. Bill Murray turned down the role because he was busy with What About Bob?. Also considered were Jeff Bridges, Richard Dreyfuss, Mel Gibson, Jeff Goldblum, John Goodman, Steve Guttenberg, Michael Keaton, Ray Liotta, Kurt Russell, Tom Selleck and Sylvester Stallone.
- Kevin Spacey was originally cast as Walker McCormick, but had to drop out due to scheduling conflicts. According to Janet Hirshenson and Jane Jenkins' book about their adventures in casting, George Clooney was looked at for the part. William Atherton turned it down because he was tired of being typecast as "the schmuck guy", while George Segal felt it was too similar to his role in Look Who's Talking.
- Christina Ricci was John Hughes' first choice for Curly Sue after Hughes had seen her in Mermaids. But Ricci was unavailable as she was busy shooting The Addams Family.
- Linda Hamilton was considered for the role of Grey, but she was unavailable, as she was shooting Terminator 2: Judgment Day at the same time. Kirstie Alley, Jamie Lee Curtis, Geena Davis, Laura Dern, Goldie Hawn, Andie MacDowell, Olivia Newton-John, Kathleen Turner and Sigourney Weaver were also considered for the role.
- Hughes had originally asked John Williams to compose the music for this film after their collaboration on Home Alone, but Williams was busy working on Hook.
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