The Red Jaguars, the unlikely duo of Pinkie Pie and Isa, had the most amazing luck during the Legends of the Hidden Temple event, passing every trial with flying colors, and ultimately winning the grand prize. On their last life in the temple, with two seconds to spare, no less!
A behind-the-scenes example: On Halloween one of the mods hosted a livestream of two Mystery Science Theater 3000 episodes with a group of players. Simultaneously CMOA as the players started coming up with their own riffs and even sang along with pieces of the theme song in the chat, AND Crowning Moment of Heartwarming that the mod thought of it and that the game has such a close group that they could spend such quality time together. A few players even postponed seeing the season finale of Atop the Fourth Wall for it!
The Eye of Argon riff was done in one night, four hours, with essentially no editing once it was all typed up, and it's been deemed by a few as one of the best riffs the game has had.
Rarity was a Crowning Pony of Awesome during the evil doubles event, busting into threads like a Big Damn Hero and kneecapping shades left and right. You do NOT mess with her friends.
Pinkie Pie defeated her shade by shooting a cake at it with the party cannon. While yelling "I AMA MAN!" no less.