Funny / The Life and Times of a Winning Pony

• Cloud Kicker's first meeting with Luna: "If Nightmare Moon came up to you, took off her robe, popped a huge wingie, and smiled at you then you'd be just a bit freaked out too."
• Pretty much the latter half of Chapter Three. 5 fillies come over, including the Crusaders, Blossomforth is drunk, and then hilarity ensues.
• And, one from Chapter 11... Cloud Kicker has fallen back in love with Fluttershy...the reveal of this is hilarious.
• In Chapter 15, we hear Derpy and Blossomforth wake up to find themselves spooning each other.
• In Chapter 16, Cloud Kicker and Rainbow Dash's confrontation with Changeling!Nimbus Gust:
  Changeling!Nimbus Gust: I suppose I should thank you, though. I admit, some of my plans did not develop entirely to my satisfaction, and the fact that you found my papers earlier than planned was unfortunate. However, I’m sure my queen will overlook such minor affairs when I present her with the corpse of one of the Element Bearers.
  Rainbow Dash: Over my dead body!
  (Beat)
  Changeling!Nimbus Gust: That would be the idea in presenting your corpse, yes.
• Cloud and Blossom relentlessly teasing Sparkler about her massive crush on Cloud's cousin Star, especially the two of them sharing a bed (they haven't done the deed, though... yet), and thoroughly enjoying the teen's reactions.
• In Chapter 22, Sparkler makes a Pinkie Promise that she has no romantic interest in Star Kicker and never will. "Less than two hours later, I caught Star and Sparkler making out behind the equipment building. So much for Pinkie Promises."
  • And not long afterwards, Pinkie somehow finds out.
• "The Pony Who Doesn't Fit Into Their Little Box" has several moments of levity despite the grim situation.
  • After her negotiations with Chrysalis, Cloudkicker summarizes the situation for the rest of the troops:
  Cloud Kicker: We’ve got a temporary truce with the bugs until the Bug Bitch-Queen, in her own words, gets tired of gloating over her victory. So we’ve got anywhere from five minutes to five years.
  • And of course, the Mood Whiplash ending. Specifically the changeling invasion's abrupt end.
• In Chapter 16 of "The Lunar Rebellion", when a misunderstanding makes Nimbus think Radiant Day is cheating on her, and he desperately tries to clear things up:
  "Milady Shadow, Nimbus Kicker, it is a pleasure. Allow me to introduce my sister, White Knight. She is my sister. And also my squire. But most importantly of all, my sister.”

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