Here are the first and final villains to appear in My Little Pony: Friendship is Magic. Nightmare Moon the first villain and Grogar the final villain. Although the Chrysalis, Tirek, and Cozy Glow were the last antagonists the Mane Six dealt with before the show ended, Grogar — even if he was Discord was in disguise — was the last new villain to be introduced.

When we were all introduced to My Little Pony: Friendship is Magic in October 10th, 2010, the very first villain of the series took the form of Nightmare Moon: When Princess Luna succumbed to her jealousy when all of the ponies paid more love and attention to Celestia and the daytime instead of her and the night, a terrible darkness — a nightmare if you will — possessed her, transforming her into the Maleficent of My Little Pony. Her envious hatred towards her sister's "perfect life" drove her to removing it, so that everypony would worship her and her night only forever. However, Celestia used the Elements of Harmony to banish her sister to the moon. A thousand moons later, Nightmare Moon returned to finish what she started, and had the night last forever. Or it would have been that way if weren't for Celestia's student, the studious Unicorn, Twilight Sparkle, and her new friends from Ponyville first using the Elements of Harmony to defeat Nightmare Moon, restore Princess Luna, and reunite the Two Sisters. Although the evil of Nightmare Moon was gone, she would appear in nightmares only.

For the next eight seasons to follow, our heroic pony pals defeated one villain after another: from Discord the spirit of chaos and Changeling Queen Chrysalis in season 2, to the dark lord King Sombra in season 3 and the power-hungry centaur, Tirek, in season 4, from the cutie mark-robbing Unicorn, Starlight Glimmer, in season 5, to the Pillars of Equestria's betrayed friend-turned-enemy Stygian in season 7, from the evil overlord from lands south of Equestria, the Storm King, in the movie, to the adorable yet psychopathic Pegasus filly, Cozy Glow, in season 8. While some like Discord, Starlight Glimmer, and Stygian changed their wicked ways and became friends of Equestria, others like Chrysalis, Sombra, Tirek, the Storm King, and Cozy Glow remained evil. And soon, we would be given one more villain before the great cartoon series ended.

Then, on April 6th, 2019, the 9th and final season of My Little Pony: Friendship is Magic began, and on that day, we were introduced to the final villain of the series — Grogar, the evil ibex who once ruled over the land that would become Equestria as "The Emperor of All He Saw." Before he made his debut in MLP:FIM, he first appeared in the first generation of My Little Pony, My Little Pony 'n Friends, as the evil ruler of Tambelon. He was also mentioned in a season 7 episode. In his debut, he united the remaining villains (Chrysalis, Tirek, Cozy Glow, and King Sombra) as part of his plan to take back his empire. The other villains, apart from Cozy, recognized Grogar for his legendary evil, when he gave life to the foulest monsters ever, and allowed them to run wild, taking what they wanted and destroy everything else. Grogar was perhaps one of the most powerful beings in the world of My Little Pony; he was able to break free of the magical bonds of Unicorn troops, which bore the strength of a thousand armies, by feeding of their fears! But his epoch of darkness was brought to an end when the Unicorn hero, Gusty the Great, took the source of his power — the Bewitching Bell — and she hid it away up in Mt. Everhoof. Although weakened, Grogar spent thousands of moons gathering power, bidding his time, waiting for the perfect opportunity to seize control of Equestria again. He observed from a distance the rises and falls of the villains, and suggested on using the Mane Six's strategy of working together to defeat them. King Sombra refused to participate and was defeated again, leaving Grogar with only Chrysalis, Tirek, and Cozy Glow. Little did they know, he was actually Discord in disguise; the reformed Draconequus pretended to be Grogar and form an alliance of villains in a misguided effort to prepare Twilight Sparkle as Equestria's new ruler. However, by October 12th, 2019, after they recovered the Bewitching Bell, Chrysalis, Tirek, and Cozy Glow double-crossed him and stole his magic, exposing his ruse. And although they would eventually be defeated in the end, Grogar's legacy still left its insidious mark. It was said the real Grogar was banished, but while we would never know where, it's likely that he was much closer than anyone could guess, and might've influenced our villains to divide Equestria briefly as his treacherous spirit is probably found in…


Both these baleful villains also have so much in common: their color scheme has shades of blue, both plotted to plunge the world into darkness, both were so ancient and were either regarded as legends or forgotten, and both were very powerful in magic. And it is even possible that Grogar might've had some connection with Nightmare Moon. Headcanon-wise, I think he was probably the one who even turned Luna into that. It could be possible.

Halloween/Nightmare Night is drawing closer, and so I thought this pic would be another addition since these two are spooky in nature and represent night, darkness, and fear pretty well. I'll see if I can do something like this featuring King Sombra. And fun fact, I actually created this from exactly last Halloween/Nightmare Night. Ain't that something? Anyway, there are some more Halloween/Nightmare Night pics to come, but don't expect too much. Everything's gotten complicated as you probably saw in one of my past status updates. Get ready for more frights.