Anyway, here's a rough chronology of MLP in the style of one of the stained-glass windows from FiM. I tried to keep the number of ponies in it to a minimum, because otherwise it would have been absolutely insane with them, even just sticking to the ones that were in the cartoons. For instance, G1 is based mostly off of Rescue at Midnight Castle (with Sundance thrown in because you can't have Megan without Sundance) and G3 is just the core seven plus Minty to round it out.
Some ponies were in multiple gens, of course; you could consider them ancestors, or just take it in stride. This is pretty much just a meta-history and isn't supposed to fit in with any of the canons. c:
Special thanks to Texel and his inexplicably in-depth knowledge of classical stained-glass windows. (He keeps reminding me that the downwards arch from G1 into Tales is not physically possible, so if anyone else is bothered by that, let me just say that I am aware and I'm calling artistic license on it. )
oh my goodness every time I look at this I just see more and more mistakes
So I hear you guys like speedruns?
List of ponies (left-to-right, top down)
Frame: Surprise; Ditzy Doo
G1: Medley; Firefly; Bow-Tie; Applejack; Ember; Megan (an honorary pony!); Sundance; Twilight
Tales: Bon-Bon; Patch; Bright-Eyes; Starlight; Sweetheart; Clover; Melody
G3: Minty; Cheerilee; Scootaloo; Pinkie Pie; Starsong; Sweetie Bell; Rainbow Dash; Toola-Roola
G4: Princess Celestia; Pinkie Pie; Rarity; Twilight Sparkle; Rainbow Dash; Applejack; Fluttershy; Princess Luna
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