In an interview from 2013, while promoting his upcoming film, How I Live Now (2013), Tom Holland was asked by a reporter what kind of role he might want to try next. When Holland replied, saying a project with action and humor would be of interest to him, the reporter asked if he would ever like to play a superhero. "Maybe Spider-Man, in ten years time," answered Holland. "The reboot of the reboot, if they do that."
(at around 1h 23 mins) Kenneth Choi (Principal Morita) also played the Howling Commando Jim Morita in Captain America: The First Avenger (2011). In the Principal's office, you can see photos of the Howling Commando, which hints that they are related, and he is his grandson.
Jennifer Connelly voices the Spider-Man computer Karen. Her husband Paul Bettany had voiced the Iron Man computer J.A.R.V.I.S. She was also cast, because of her appearance in the John Hughes produced Career Opportunities (1991). "Homecoming" pays homage to Hughes' high school films, and casting Connelly was done as a tribute to his career. Connelly was also previously cast as Elizabeth "Betty" Ross in Hulk (2003).
(at around 1h 11 mins) Aaron Davis (Donald Glover) mentions he has a nephew. In the comics, Aaron Davis is the Ultimate Marvel Universe version of The Prowler, and his nephew is Miles Morales, the second Ultimate Spider-Man. Artist Sara Pichelli originally modeled Miles after Glover and President Barack Obama, and Glover voiced Miles in Ultimate Spider-Man (2012).
The cast had to watch a John Hughes movie marathon to prepare. This movie is first and foremost a coming-of-age tale, so Jon Watts turned to the master of such stories: John Hughes. "He gave us a lot of movies to watch", Tom Holland said during an interview with PopSugar UK. "God, there's so many movies, and we basically just all sat down in my house in Atlanta, all the cast, and we just watched them all in one day, and just had like a Domino's day. It was amazing, The Breakfast Club (1985), Ferris Bueller's Day Off (1986), Pretty in Pink (1986), there were loads of them."