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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Spyro the Dragon
The classic Spyro and Legend of Spyro series take place in the same universe but...
Classic Spyro's world was the one before the TLOS and was destroyed by the Destroyer. TLOS Spyro was the reincarnation of the original Spyro (differences being due to being raised by dragonflies) and succeeds where he fails. Sorry, this has been running through my head this whole time.

Alternatively, the Legend of Spyro really is a prequel to the classic series.
When Spyro recreates the world at the end of Dawn of the Dragon, it sets up the classic series realms. It could also be entirely possible that the Spyro in the classic series is really a descendant of the Lo S Spyro and Cynder.

Building on the above two WMGs, Skyland is the future after classic Spyro.
Legend of Spyro is the past, then the world is destroyed and recreated by Spyro, and over time changes into classic Spyro. Then Skylanders is the future (It DOES seem to have more advanced technology, what with one of the elements being "Tech.") The three Spyros and Sparxes and two Hunters and Cynders are reincarnations.
  • There's a page on deviantART that explains how this theory could work; [1]

The classic and Legend worlds are parallel to each other
When you think about it. They could be something like yin and yang. The classic world is very bright, cheery, and while there is evil, they're normally not as dangerious and threating as most of the sterotypical big bads out there. Meanwhile, the Lo S world is much darker and edgier, with things being realistic in scenery and the villains are much more bloodthirsty then the classic villains. It could be said that the main characters of both worlds are the same people, only their destinies being radicially different.

Going off the above WMG, there exist versions of Cynder, Ignitus, and the Chronicler in the classic universe.
Of course, since the world is majorly different from the LoS universe, their personalities are probably very different as well.

Malefor IS the original Spyro
Think about it, original Purple Dragon, gleefully taught by his masters, considered a hero, Prowlus even said Malefor and Spyro were very similar as children. Eventually, he went insane from constantly having to save the world (or possibly a villain performing a Break the Cutie on him) and turned evil, and was renamed Malefor in response to his corruption. If true, this would make his Not So Different speech very chilling indeed.
  • This also adds to the creepiness of one of the dragons freed in the first game; he mentions they "always knew", but vanishes before this can be explained.
  • This actually makes a lot of sense... and it also just ruined this troper's childhood.
    • But then why is he named Malefore and not Spyro I or something?
      • He felt he needed to change his name after his Face-Heel Turn? Though, it does beg the question of why the dragons decided to name someone else Spyro, with all the negative connotations that name would have...
    • So the sequel takes place centuries in the future with Spyro, Sparx, and Hunter being reincarnations?

TLOS is actually just a nightmare that Classic Spyro had one night
He dreamed that he became a lousy hero, and that Hunter was huge and muscular. And that Moneybags was nowhere to be seen.
  • But Hunter isn't particularly muscular in Lo S. He just has a more realistic cheetah face. Why would he be muscular? And Moneybags not bugging him would be a GOOD thing for Spyro.

Moneybags is behind everything
He bribed Ripto to lock everyone up because he knew Spyro would come, and that meant he'd get more money! Plus, he sold Bianca into slavery with the Sorceress because he had her locked up like the animals. Heck! The events of the first game were probably brought upon us by Moneybags.
  • Moneybags probably started the TLOS series too. Maybe even Skylanders.

The reason there are gems lying around everywhere is because they're really low quality.
Moneybags doesn't care, he just sees the shiny gems and wants them now! But the various residents don't care about them because not only do they not need them, the gems simply aren't worth enough — you'd have to go on a huge collecting spree to buy anything, even if there was anything to buy.
  • The earlier games say the gems were stolen from the dragons/Avalar/Forgotten Worlds by the villains.

The Spyro 1 home worlds represent a caste system
Think about it. The way the levels increase in difficulty is similar to how higher castes have stricter rules. The balloon fare is more expensive because it costs more to get to a richer neighborhood. Gnasty Gnorc's world is the last one because he put himself at the top, above all of the dragons.
  • ... except for the fact that the Artisans seem to be the most important and respected dragons generally, and Nestor, the very first dragon you free, is even implied to be some sort of ruler (or at least a senior elder). If anything, the caste system seems to run in reverse order; the highly respected Artisans on top, the Peace Keepers, responsible for law and order, next, the self-important (though not utterly unjustifiably so) Magic Crafters after that, then the slightly country-ish Beast Makers, then the airy-fairy Dream Weavers - and finally the Dragon Junkyard, which truly is the pits of the Dragon Realms. The higher transport fees may simply be because you're going to a rougher neighbourhood each time - more risk for the balloonists (even though they seem to have no problem parking in the previous neighbourhood...).

Skylanders will set up a Crisis Crossover
Think about it. The Big Bad is able to hurl people into alternate worlds. How could they overlook the opportunity to crossover the three Spyros? Particularly with the outcry from older fans at each new universe. What better way to take advantage of that than featuring all three in one game?

Spyro is a Time Lord.
I believe my troper duties are done for today.

Moneybags is omnipotent.
Think about it. He shows up in, like, four places simulataneously in Autumn Plains in the second game. And in the third game, if you don't pay him to go into the ice-skating minigame, he scoffs, "What are you saving your money for, another sequel?" Then Enter the Dragonfly comes out, and we all know THAT wasn't exactly the best game ever... Then at the Agent 9 cage, he tells Spyro, "I bet you wish you had YOUR own action figure..." in a knowing way YEARS before Skylanders!
  • Then why does he get his ass kicked by all the animal partners in Year of the Dragon after releasing them?
    • He's omniopotent yet incredibly greedy and stupid?
    • Alternatively, Moneybags is an example of Me's a Crowd and is a Seer. Other than that, he's just a greedy bear.
    • Or, you know, he could be letting them kick his butt intentionally so it seems like he's less powerful than he actually is.

There are more than three continuities
It's not just "Classic", "Legend of Spyro", and "Skylanders". There are things in games like Hero's Tail and Shadow Legacy that contradict earlier canon such as Hunter using a bow in later titles, Moneybag's and Bentley in general, the Dragon Spirit randomly being in Enter the Dragonfly, and the two different stories about how the Dragon Realms was discovered. There's also Bianca's Chickification and the general lack of Elora in post-Insomniac titles.

Spyro is not twelve
In Spyro Yearof The Dragon we're shown ages hatch every twelve years, which pins Spyro and his friends from Spyro: A Hero's Tail at at at least twelve. What if he was even older chronologically but dragons age differently from "normal" species.

The Legend Of Spyro is just that, a legend
Not just any legend though, a fanfic legend, written by Ember. Cynder is her self-insert by the way.
SPY FoxWMG/Video GamesS.T.A.L.K.E.R.

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