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Conquer half of European Russia as Finland during the winter war. From Murmansk to Riga to Moscow and Stalingrad. Using 25 divisions. HoI4. Possibly more sad than funny. The Soviets still had an insane numerical superiority in the end, yet capitulated. They didn't even use their vastly superior air force, so I always had full air superiority. This was around release.

HOI2 using WIF, quite a few years ago: Lose 200 divisions as the Soviet Union, due to being encircled by two Finnish divisions. Reason? The purge reduces the organisation of Soviet divisions around 1939 to something like 1 or 2, while the AI gets all sorts of cheats and bonuses to their capabilities, resulting in ridiculous multiple thousand division sized armies among Germany and the USSR when played by AI.

Other funny things: Try to attack a small member of the HRE in EU3 as Poland, using the Magna Mundi mod. Heaven starts raining upon me, everything bad imaginable happens, I get destroyed and cut down to size and the emperor attacks me with 200k men that spawned from nowhere. Got framed.

CK2: Discovered a plot where my mother wants to murder my brother. Ended the plot. My mother then proceeds to murder me. Playing as my next heir I murder her but get murdered by my new character's mother. The murder spree within the family continues until my entire dynasty died.
 
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Started as a new player in Ireland ,created a black ruler , installed Way of Life DLC when it first came out and chose Seduction focus ..

Realized if I wanted to keep playing as a black Character in Ireland I'd have to do some VERY bad things ..

Preceeded to have as many children as possible via wives and mistresses, when a wife would get too old to have children onto the next one ...

Meanwhile my character seduced every woman on the island possible as efficiently as could be managed ,no time for war or crusades or a trip to the Holy lands ...just banging. ....

After the first generation of children came of age it was then time for incest on a MASSIVE scale (because illegitimate children from "other" women didn't show as being your own kids " )

After a few generations of this ,managed to turn 25% of Ireland black .
 
Started as a new player in Ireland ,created a black ruler , installed Way of Life DLC when it first came out and chose Seduction focus ..

Realized if I wanted to keep playing as a black Character in Ireland I'd have to do some VERY bad things ..

Preceeded to have as many children as possible via wives and mistresses, when a wife would get too old to have children onto the next one ...

Meanwhile my character seduced every woman on the island possible as efficiently as could be managed ,no time for war or crusades or a trip to the Holy lands ...just banging. ....

After the first generation of children came of age it was then time for incest on a MASSIVE scale (because illegitimate children from "other" women didn't show as being your own kids " )

After a few generations of this ,managed to turn 25% of Ireland black .
Should have played in Scotland.

250px-Demoman.png
 
Personally, I have a giggle when I fight some tough-brass German General like von Manstein with a level 8 Lakshmi Saghsl.

Funniest thing I have experienced though was playing as the 10 year old princess of Persia in CKII, child after king dies (ultimogenitur), and surviving with literally everyone hating my guts. 2 assassins, 1 i think i personally killed, a pedophilic uncle event, became an adult, killed all the a-holes, and beat Death at a game of chess, all while having "You got the touch" playing in the background. Nothing more badass could have happened.


Maybe killing the Aztec king while playing as Genghis Khan is more badass.
 
Started as a new player in Ireland ,created a black ruler , installed Way of Life DLC when it first came out and chose Seduction focus ..

Realized if I wanted to keep playing as a black Character in Ireland I'd have to do some VERY bad things ..

Preceeded to have as many children as possible via wives and mistresses, when a wife would get too old to have children onto the next one ...

Meanwhile my character seduced every woman on the island possible as efficiently as could be managed ,no time for war or crusades or a trip to the Holy lands ...just banging. ....

After the first generation of children came of age it was then time for incest on a MASSIVE scale (because illegitimate children from "other" women didn't show as being your own kids " )

After a few generations of this ,managed to turn 25% of Ireland black .

this is awesome. if only you could've turned ireland into black horses.
 
Attempting to play HOI4 with a couple buds in a weird way: every player controls one general and his army, all playing the same country, while someone heads the politics/diplomacy/focus tree.

The ultimate result was a lot of discussion and arguing over who we should focus on, but it all went reasonably well because we were too cowardly and played Germany + the HOI4 AI isn't quite known for their legendary stratagems...

The highlight probably was when the player in control of the border with the french completely forgot about the existence of the Maginot line and killed our entire manpower trying to cross it, resulting in disaster as the Soviets sensed weakness and invaded. Disaster was averted by literally parachuting a guy into Paris forcing an early surrender from the French and then sending everything on the soviets' way.
 
My game starting in ck2 Charlemagne start as Venice. Was doing the usual run of expanding local control, crushing the other houses and making myself lord of the Adriatic. I had made myself the "Kingdom of Venice" title (you start as a duke in Charlemagne), and was feeling pretty good about things.

Then the year 900 hits, and the Crusades start. I look over to realize that while I wasn't paying attention Paris had fallen to the Umayyads (or whatever house ruled their kingdom by then). I proceeded to use mercenaries to win the 1st Crusade and became king of Aquitaine. Then the next Crusade is declared on Jerusalem. And another on Andalusia. So now I am the doge of Venice, ruler of the Adriatic, the Holy Land, half of Spain and most of France.

Naturally I make myself a new empire title - Empire of Venice.
 
Played as a Zoroastrian Persian character in Karen.

A few Generations the son was banging the mother.

Freud would be proud.
 
that moment when the Oedipus complex moves too damn fast!

He just REALLY loved his mother!


What's wrong with that?!


Everything!
 
Played as a Zoroastrian Persian character in Karen.

A few Generations the son was banging the mother.

Freud would be proud.
Well, everything being legal sucks the fun out of it. I seduced a sister as a catholic ruler once, naturally marriage wasn't an option, but wait, this is CK+ and it has "elope" plot - when your lover escapes her court and joins yours as a wife. So here I go, conspiring with my vassals, so she could escape my court with me. Few months of careful planning later - courtier escape message pops up. "That wench!" immediately my character thinks, getting -100 opinion on her, but few days later she finally shows backs, saying her escape was a success and we can finally be together, "+50 eloped together" my character thought, my vassals were happy about successful plot as well.
And everyone lived happily ever after. Except my character, who still couldn't forgive his new wife for her escape. And, well, kids... poor things.
 
I made my horse the Court Physician. Then I made my horse Bishop of the Isle of Man. Then I made my horse an Antipope. Then I deposed the real pope and made my horse the only pope in the world. Then I made my horse immortal, leaving the papacy under the control of a horse for all time.
 
Vicky 2, trapped 100k Turks at Gallipoli as Greece around 1910. and won the war thx to it, basically reforming Byzantium :D
And let's not even start on the hilarity of province ownership in EU2/FTG. I have seen Persia own a province in Scotland once. Also, when Timurids pop it is border-gore galore
 
In CKII as the Emperor of Frisia I won a Crusade for Italy against the Jewish HRE. For some reason it became part of France after that. The French Empire didn't even send troops to Italy...