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Roxanne dumped Max (or vice versa)
That explains Mona and her lack of appearing beyond House of Mouse. Not soon after that appearance, they broke up. It's not like high school sweethearts always stay together anyway; very few do, you move on to new people.

Peg and Pistol died in a car accident between the Goof Troop and A Goofy Movie
That's why Pete is much more of a Jerkass in the movie, especially to PJ. He's been going through a rough patch after his wife and daughter died, and is just trying to take it out on the people closest to him.
  • Replace dying with a divorce/separation and it works as well.

Pete and Peg got divorced
Peg got fed up with Pete's money-grubbing schemes and demanded a divorce, taking Pistol with her and leaving PJ with Pete. Most likely why Pete's Jerkass meter went up in this movie.
  • Though this does beg the question why she took only Pistol and left PJ with Pete; Peg is defintiely not the kind of person to leave one her kids with someone she no longer trusts.
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Pete and Peg are still married, but Peg isn’t seen due to some... Issues with Pistol
In other words: puberty was too kind to Pistol and she inherited her mother’s Impossible Hourglass Figure. Sometime before An Extremely Goofy Movie Pistol got in a relationship with sleaze who lusted for her body... Whether Pistol was willing or not, she got pregnant and the deadbeat guy fled in terror at the prospect at being a father.. As well as from a very angry Pete. After the child is born, Pistol felt the need to move out to take care of her child and not be a burden on her family. Peg and Pete then agree that she needs someone to help her, specifically Peg who moves in with her daughter to help raise the baby and as well as help Pistol mentally. Pete and PJ are worried out of their gourds over Pistol and her baby in the meantime, which makes Pete more of a Jerkass and PJ more nervous.

Stacey's popularity
I've come up with a number of explanations for why Stacey is popular despite her geeky appearance:
  • She throws awesome parties (the most likely explanation)
  • Her being friends with Roxanne elevates her coolness level (though we never get any indication that Roxanne is popular)
  • Max makes her look much cooler by comparison (the funniest explanation)

Mickey's Twice Upon a Christmas takes place in a different continuity from these movies
Those movies don't look Goof Troop canon so why would Roxanne exist and/or be with Max?
  • Possibly averted since Once Upon A Christmas seems to be a Goof Troop prequel
    • What makes this more likely isn't the lack of Roxanne—Max was clearly single in college anyway, unless he was cheating—but the lack of Sylvia. Also, Once Upon a Christmas appears to be a similar but inexact continuity to Goof Troop given that Pete appears to be single and without children (hard evidence) and that Max and Goofy already live in his neighborhood (soft evidence).
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Kimmy (Goofy's photo baby) is Roxanne's sister.
They have similar head shapes and noses (in a universe where that means a lot). Further, we only ever see Roxanne's father, and likewise, only Kimmy's mother.

Max at some point in his adulthood changes his name to George Geef
It could be that his embarrassment of his father got worse, it could be that Max got in trouble with the mob (and ended up with his ears chopped off). Either way, the fact that Max looks like the George Geef version of Goofy suggests that there may be more than a mere shout out or gag.

Max and Roxanne broke up because Roxanne's dad is a Child-Basher Basher.
He thinks the innocence of childhood should be protected at all costs. While strange boys who come to see his daughter get growls and glares, people who treat their own children badly get to meet his fists. Well, after Max's best friend's dad and girlfriend's dad met, the former gave Max a Sadistic Choice—either break up with the girl or never see his best friend again. Max reasoned 1) his best friend needs him more, and 2) they'd known each other longer, and made his decision.

Max lied.

It does not take three and a half cups of sugar to get to the moon.

  • You, eh, you counted that?

Powerline is related to Max and Goofy
Goofy said that the perfect cast had been handed down through the family for generations, and it's pretty random, so how else could Powerline have managed to do it after only having seen part of it? He's a distant cousin of Goofy's.
  • This also explains their similarly-shaped muzzles.

Max broke up with Roxanne because she was obsessed with Goofy.
What she loved most about Max was his laugh. After meeting his dad at the end of the movie, she saw that Goofy could do the laugh more often, and she harbored some sort of crush on him. Max caught onto this, broke up with her, and went back to wanting to distance himself from his dad again by the time he goes to college.

Goofy's father is the original Goofy starting from 1932 and the current Goofy from this movie and Goof Troop is really a grown up Goofy Jr.
  • Perhaps that's also true with Pete. The original Pete is really his father and the current Pete from the series is Pete Junior (introduced in the short Bellboy Donald) grown up. This is evident considering the personality differences between the original Pete Junior and PJ.
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That security guard came out perfectly fine.
Despite fan concerns, his crash into the big screen didn't seem that much worse than the many other Amusing Injuries acquired in this universe. The only reason we don't see him afterwards is because the movie immediately cuts from the performance to the Goofs returning home. More likely than not, the guard stumbled out of that mess very sore and disoriented and attempted to capture Max again after the performance was over, only for Powerline to vouch for him.

Max has a depressive disorder
He deals with it internally mostly, but the only person he can ever really take it out on is Goofy, because Max knows he's the only one who will understand in whatever capacity Goofy can. That's why he's still with Roxanne after college, working as a valet at his dad's friend's club. He doesn't want to be too far away from Goofy in case something starts bothering him and he needs someone to take it out on.

Roxanne and Mona are literally the same person
Roxanne and Mona have the same voice, the same general facial features, and both even have moles near their left eyes. The only difference is that Mona has short, brown hair instead of long red hair, blue eyes instead of black, and a darker nose, all of which are easily modifiable traits. Perhaps Roxanne witnessed a crime and had to enter Witness Protection for awhile, or for some reason she wasn’t allowed to date Max (or perhaps anyone) during college, or maybe she’s a spy. Whatever the reason, Roxanne took on a new identity and appearance in order to continue her relationship with Max until whatever forced her to adopt a Secret Identity was resolved, which would explain why they go from dating in high school to Max dating a Suspiciously Similar Substitute, and then back to dating Roxanne again as if they had never stopped dating after college.

Max and Roxanne are still dating, it’s just lower key since Max dosen’t want Goofy interfering and “helping”
Especially in the sequel where Goody and Max are going to the same college. After the events of the second movie however, Max lightens up and no longer minds if Goofy tries give advice on dating or acts as a chaperone.

Roxanne is a dog/human hybrid.

Roxanne looks human in almost every way, except for her dog-like nose. She evidently takes her looks mostly from her mother as she doesn’t look very much like her father, and his appearance is clearly more doglike than Roxanne's. We never see what her mother looks like so it’s possible she could be fully human (or perhaps she herself is a dog/human hybrid).

If they had made a 3rd Goofy Movie
It would have served as a midquel to A goofy movie, and an extremely goofy movie. Principal Mazur would halved returned to do everything in his power to harm Goofy and his son Max for ending up on stage with Powerline, and possibly kill Max. But he would've fail, and either get sent to prison, or a asylum. Or he would halved been killed off.
Alternatively to the Above, if there is a Sequel to An Extremely Goofy Movie
And then, it would be a Video Game in the Wide Open Sandbox genre that is the Actionized Sequel to both films in addition to a hypothetical Goof Troop sequel series in the vein of Rockstar's titles such as Grand Theft Auto: San Andreas, Grand Theft Auto V and the Red Dead Redemption duology (RDR II in particular), THQ's Saint's Row series and more. The wedding concert could take place in Seattle.
Goofy dose know Power line, Max just didn't ask.
Why else would he allow them to crash his concert? In my mind Powerline was a few years younger than Goof in college (who he would know as George), but they were good friends until Goofy had to drop out to support his family. Goofy didn't make the connection since the guy he knew was a shy, quiet freshmen.
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