I have had a few but some of the ai is great.
I had just picked up anneke as a follower and i saw a mammoth or three in the distance. I decided to sneak up on them and see how her archery was. She snuck right behind me but as we got close she says
"I have a bad feeling about this"
Ha! Smart girl!

Oh yeah, one of my favorites! Accidentally ran into a Forsworn camp prior to knowing wtf a Forsworn was. It was an accident, because I was chasing a dragon UP a mountain. No one paid me any mind at first because... [censored]!!! a Dragon!!! But as I made my way through their ginormous camp, more and more began attacking me. I had two Briarhearts on me and a few archers before I knew it. I started killing indiscriminately, hacking, circling, power attacking. I killed everyone!!! Then, I'm doing a circle, making sure everyone around me is dead, when the whole screen shakes. I circle faster. The screen shakes. I look down. A goat. Their [censored] goat is ramming me. All I can think is, "Hey dude, they were probably going to eat you. I did you a FAVOR!" Then I killed him for being an ass.

So, I charge up the last of the stairs, creep across a ledge to get to the dragon, where he is fighting a cave bear, GET to the (epic?) battle of bear and dragon, sword raised, ready to kill the dragon I'd spent 10 minutes pursuing, JUST in time to watch the bear swat my dragon one last time...KILLING my dragon. The bear charged me and I killed it with one or two swings of my sword. I was so let down... I lol'd at the whole thing though.

Man, this had me laughing so hard at work that I have tears in the corners of my eyes. I had a similar experience with a pie and was like, "What the...? Why does no one else notice the haunted pie on the table?"

yeah similar thing happened to me... dragon dropped dead from the sky with no loot (no bones and scales)

Once, while using the Speechcraft exploit at the Black-Briar Meadery in Riften, Ungrien was going on and on about how Maven Black-Briar is a terrible employer... all while Maven had walked up behind the poor fellow and stared over his shoulder at me. She stayed there through about 5 or 6 of his responses about her awfulness before moving on.

I suspect Ungrien won't be getting a Christmas bonus.

I accidentally hit a guard during a fight with a dragon and the guard tried to arrest me. During the fight with the dragon.

I play dead is dead streaming and once I ran away from three salmer after killing two others. I went through a loading door thinking they wouldn't follow. Well they did. Scared the crap outta me. It was in the markarth dwemer ruin. I ran backward while I was trying to think of what to do. One of them alone takes about 25 arrows on master difficulty so I paralyze shot one in the knee to give me a few seconds to think. They were gaining quick and I had no where to run so I froze time, looked over the edge, and dove for a deep spot of water. Most insane moment in my skyrim life. Everyone in the channel about crapped a brick!!!

Fun with Giants;

While exploring I made my way over a little rocky hill when I noticed a giant and his mammoth. While I contemplated sniping the giant from my advantageous perch, a group of four bandits came rushing in toward the giant. My mind did a '/popcorn' moment as I watched the mammoth intercept the ragtag group and easily stamped out two of the hapless fools. While I'm laughing my [censored] off, the two remaining bandits decide it's best to retreat from a certain doom. One of the best random encounters that had nothing to do with me.

Another giant encounter involving my girlfriends character;

We watched two giants beat the holy tar out of a couple of Forsworn or bandits. One giant took a swing which created a big cloud of dust. The other giant nailed his target dead on which sent the poor soul flying towards the heavens. We watched as this corpse flew higher and higher passing through clouds. I don't believe it ever came back down. I do think it is circling the planet however.

Oh and one of the best lines I've heard to my girlfriends Khajit toon: "You look like my sisters cat....I killed that too!"

Not so much funny as weird tonight...

I left Riften and passed my horse standing next to the cart guy's horse. I said hi to him (I never use him; he just stalks me) and went to the honey place to poke around (just checking barrels and wasting time--no real point).

Then I heard a guy yell, "Hey!" I saw nothing but figured I should go see what's up, as that's not a normal line from an NPC, really. When I walked back (a short distance, you'll note), my horse was standing to the other side of the city doors. "How on earth did you get over here?" I wondered. Then a splotchy horse walked past me, followed by the cart guy, who got back on his cart. A little while later, I found a dead necromancer by the bushes in front of my horse.

I'm still trying to figure out what happened. That area's supposed to be a "safe zone," apart from dragons (i.e., you never run into aggros close to cities, in my experience). As far as I can guess, anyway, this necromancer turned up, and two of the non-carted horses (mine included) beat him down, presumably with the cart driver trying to feebly assist.

It might be a good moment to note that I've never had a normal experience outside Riften yet.

I wander into the bee and barb, tip my hat to mercurio (who had adventured with me previously) & he's quietly drinking an ale in the corner

Next thing i bump into a loudmouth orc and well, us orcs dont like to be pushed around. So i says to the Orc i says "listen here pal, BACK OFF!". He whips out his sword an board and im like "yo its ON!"

Mercurio gets up (in fact the whole bar gets up to defend me), charges his lazer fingers of epicness and proceeds to electrocute the entire bar including the staff. Then he sits back down to finish his ale

Mercurio, you so cray-zeh

Hearing guards say "Psst, I know who you are.... Hail Sithis."

It's not a unique thing, but the Louis Letrush glitch makes me smile.

I left town and saw my horse rise up about 6 inches in the air and found 2 Louises, one in the ground. The next time, there were 3. I (futilely) hoped it would just keep going and there'd be an army of Louises along the road... Every time I leave the gate now, I think, "I'd better go see how the Louises are doing" and go say hi to them.

Ah, and another very minor thing that amused me...I whacked an archer with my axe; she fell off the tower ledge and actually screamed "AAAIIIIIEEEE!" Beautiful.

I hate when I'm up somewhere high up and that I'm gonna jump down in the river or lake and bypass everything- No, its only two feet deep and I die on impact. First time I thought it was funny, the other times it was annoying. =_=;

I walked into the Hall of the Elements and saw the Arch Mage falling from the ceiling and almost kill himself. I guess his attempt at recreating the long lost art of Levitation failed? Lol

Just killed a fire dragon at Riverwood. The village is in ruins. The blacksmith walks up, looks at my flaming sword and says, "Careful where you wave that thing, you could set this place alight"

well every time a dragon lands in town i get in trouble for it. I know it's not because i hit somebody by accident or anything like that because i'v tested that; the last time a dragon landed in a town on my game i didn't do anything, just sat back and let the guards handle things. after they killed the dragon i got a nice fat murder fine i was like wtf lol

Hrongar: I'm not a man, I'm a weapon in human form. Just unsheathe me, and point me at the enemy

so im up in the ice sheets at top of map ice as far as i can see when i see a black dot on screen it moving fast oh crp set my magic up pull out my swords i drink a fortify potion im ready its coming closer and...... its a bunny wtf it doing out here the people in dorm had a good laugh about that

LMFAO!

this one thing was funnier then the entire OP's thread. Still funny overall though haha

Running through the woods I came across a couple of hunters chasing something. I guess they really get pumped hunting deer because one of them starts yelling "victory, or Sovngarde!".

I wabbajacked a hunter riding a horse, who found himself riding a chicken.

I was doing a DB kill and had Lydia with me. Got up on a high spot and stealth killed right next to a guard, the guard started wandering around for whoever did it then stopped looking for me. I walked down back into the town to loot the body (of course) and start to leave when Lydia and the guard start fighting. Nobody seems to care, not even the other guards so i just stand their and watch. Lydia then hits a crushing blow and knocks the guard on all fours and she tries to crawl away yelling "I give up!". Lydia then pick her up and jabs her sword through the guard's back, it was great.

With 100 in Pickpocket, one of my pleasures is to remove the clothes/cuirass of NPCs who insult me.

"What do you want cat?"
*Removes guard's cuirass

So from time to time I'll run into NPCs or guards walking in their underpants. And I'm still trying to see how it's physically possible to remove a man's cuirass and greaves while keeping the boots and the helmet on place...without him noticing. For the rest of the game.

sure but you gotta admit, that was one heck of a good death for the old orc.

As for me, well I always love it when the enemies are throwing insults at me while I'm in the act of slitting their throats. I also have Louis Letrush sunk into the ground up to his waist outside whiterun, looks rather odd.

One of the funniest, was while sneaking around outside, I make my way down a cliff, into an area with a large overhang, oddly enough, there's a dragon wall at the back, weird. I make my way past some fallen rocks and learn a new word, suddenly I hear the sound of breathing. I turn around, turns out one of the rocks I stepped around was a sleeping dragon, curled up into a ball. Was rather funny.
P.S. I whipped out my dagger and managed to stealth kill him in 2 hits, he never even got off the ground.

Funniest event today: Taking Ghorbash the Iron Hand around as a companion, he's really not very good with traps. Seems every dungeon I go through, I sneak along, and behind me, thump thump go his boots, clank clank goes his armor, and 'shink' go the spikes from the wall. One of his favourites was one of those swinging spiked wall traps, first time, he stepped on the pressure plate and it smacked him in the face (I might want to point out that my last char with Lydia in tow died on this very same trap when Lydia set it off), he sank down to his knees, crawled around for a bit, then staggered back to his feet, stood up, and, while I'm shouting "No" at the screen, takes a step backwards onto the pressure plate again. He proceeded to do this 5 more times, I have no idea how he survived, health was so low it was an almost invisible sliver.