- Acclaimed Flop: The film did make back its budget, but it wasn't as successful as Disney thought it would be and the company decided not to take a chance on the proposed three sequels. Despite this, it's generally regarded as one of Disney's best live-action offerings of the 2000s.
- Actor Allusion:
- After they resisted it the entire film, the Principal's last line is, "I'm not Wonder Woman, you know." She's played by Lynda Carter. It is also a Casting Gag, since Carter's character in Sky High is the principal of the titular school, and her character in Wonder Woman is a superhero.
- Bruce Campbell's character has a thing for the word "boom". It was rather disappointing to learn that he didn't have a boomstick.
- This isn't the first time Kurt Russell played a character with super strength in a Disney film.
- Awesome, Dear Boy: The reason why Mike Mitchell signed on direct the film is that he had the chance to work with the actors who played four of his favourite science-fiction cult heroes, namely Lynda Carter (Wonder Woman), Kurt Russell (Snake Plissken), Bruce Campbell (Ash Williams) and Cloris Leachman (Frau Blucher *Horse whinney*).
- Deleted Scene: The movie originally opened with the Commander and Jetstream fighting Royal Pain, long before Wills birth. Footage from this fight made it into a flashback, and missing trailer scenes, before Disney put the whole clip on the DVD.
- Fake American: It's somewhat notable that All American Boy is played by Canadian born Dave Foley.
- Follow the Leader: Zoom: Academy for Superheroes was rushed into theaters shortly after Sky High came out, and the epic failure of the ripoff is probably why more films of this subgenre are not being made. Ironically, Sky High is sort-of a ripoff of the old DCOM Up Up and Away itself.
- I Want You to Meet an Old Friend of Mine: The school's Nurse Spex is played by Cloris Leachman, who played Queen Hippolyta to Lynda Carter's Wonder Woman.
- Playing Gertrude: Minor example. The youngest of the adult cast was Jim Rash at 33, playing Mr. Grayson, and while not super-young in the grand scheme of things, it is too young to believably be the father of seventeen-year-old Gwen (played by nineteen-year-old Mary Elizabeth Winstead).
- Real-Life Relative:
- Retroactive Recognition: Many will recognize Danielle Panabaker as the actress who plays Caitlin Snow / Killer Frost on The Flash (2014).
- Sequel Gap: After 11 years, it was announced that Disney was finally going to produce a sequel. It's still in preproduction, so it's unknown if it'll be animated, a "next generation"-type scenario, or a lot of recasting (at least with the teen characters), but it is getting made.
- Those Two Actors:
- You know who else was in The Tick? Patrick Warburton, who provides Sue's Royal Pain voice.
- Dave Foley and Kevin McDonald from The Kids in the Hall.
- Mary Elizabeth Winstead and Kurt Russell were also in Deathproof. Furthermore, Russell was also the main protagonist in the 1982 movie The Thing (1982) and Winstead his Distaff Counterpart in the 2011 prequel.
- What Could Have Been: Word of God from a production crew member on the Internet Movie Database forums says that there were originally going to be four movies, one for each of Will's years at Sky High, with the scope of the plot getting grander in each one, culminating in a villain powerful enough to threaten the entire universe in the final film. As well, Baron Battle would've made a physical appearance, and Warren and Layla would become the Official Couple. Now that the movie is getting a sequel, it's unknown if any of this will become a reality.
Trivia / Sky High (2005)