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.
The classic and Legend worlds are parallel to each otherWhen 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 SpyroThink 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.
TLOS is actually just a nightmare that Classic Spyro had one nightHe dreamed that he became a lousy hero, and that Hunter was huge and muscular. And that Moneybags was nowhere to be seen.
Moneybags is behind everythingHe 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.
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 Spyro 1 home worlds represent a caste systemThink 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.
Skylanders will set up a Crisis CrossoverThink 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!
There are more than three continuitiesIt'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 twelveIn 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 legendNot just any legend though, a fanfic legend, written by Ember. Cynder is her self-insert by the way.