The 90's were a much bolder time for Disney, back when they were less occupied with remaking their 'golden age' flicks into live action and more interested in expanding and exploring various properties in organic ways. While the ill-fated Atlantis series (a franchise that came before its time) was perhaps the end of this era of deeper dives, the early days of Disney's televised escapades were surprisingly refreshing in retrospect of where they are twenty plus years later.
For all intents and purposes, Disney was taking its pre-established 'OC's' and casting them in literal 'AU' style running series, around the very time the premise of fanfiction was beginning to flourish (in part thanks to another Disney property, Gargoyles). DuckTales, Chip N' Dale: Rescue Rangers, Darkwing Duck, and TaleSpin were all taking established Disney characters and re-fitting them into new settings and worlds with context and history not unlike a literal alternate universe fanfic - this was on top of similarly fanfic-esque shows like The Little Mermaid and Aladdin. But there is one property which got this treatment on such a scale that it warranted a full-on, premiere theatrical release in the form of A Goofy Movie.
Framed as a sort of conclusion to a 60+ episode run of TV series Goof Troop, A Goofy Movie was the culmination of taking a long-running original Disney icon, slapping him into a domestic suburban alternate universe, and making him a single father. The series that ran before it doesn't even need to be watched to appreciate the film, which functions as a standalone story in its own right and is to date one of Disney's most intriguing movies. Nothing Disney has released in movie theaters since has approached such an earnest concept as literal alternate universe fanfic territory, and A Goofy Movie in many ways delivers on what many who grew up in the 90's might wish to see today: beloved characters presented as grounded, struggling people just trying to lead happy lives.
What's even more special here is that last part: a film about everyday struggles. The other sibling series mentioned above all showed the characters still living larger lives than a dorky single dad just trying to raise his son. Scrooge McDuck was a treasure hunter, Chip N' Dale were, well, Rescue Rangers, Darkwing Duck was a superhero, and even Baloo is a bush pilot in TaleSpin. Not to speak of the magic-laced settings of Ariel or Aladdin, this was all more exotic and adventurous than taking family photos in a corner of a shopping mall. .
Just the opening scene of A Goofy Movie sets the stage in an almost Marvel Cinematic Universe style, decades before such a thing came to pass. It leans a bit on the expectation that the audience knows who Goofy is already, yet its setup and premise is mundane in a way the Marvel movies wouldn't dare. The son of Goofy -- to us as iconic and fantastical as most any other cartoon characters -- has a nightmare in which his body transforms with exaggerated effect to highlight a subconscious shame he experiences in being his father's son. It's surprisingly dark in a very real and relatable sense, with the bonus being that Goofy is, to the audience, a figure whose mannerisms and appearance are historic to the medium of cartoons, yet in this world he's just a dorky single dad. There's layers of meaning here that even the MCU can barely scrape at given its ever-pressing need to push bombastic action and bigger and bigger stakes.
Disney has in some ways been learning from the strange yet bold-for-its-time example A Goofy Movie set - the DuckTales reboot and some of Mickey's more modern escapades touch on family themes that the audience can relate to. Even things like Looney Tunes and the Muppets have been trying to adapt their characters to more modernized, 'everyday person' styles, but A Goofy Movie still stands as a surprisingly watchable film after all this time and a wonderful, quirky experiment in how 'literal AU fanfic' creativity can give new life to a static character.
A Goofy Movie can be streamed on Disney+.