I guess the funniest thing that happened to me was (I forget where I was ) but I was in my werewolf form and I encountered a man named brill and he said to me "ought to put on some clothes, bound to upset some people" lol

Probably when my Argonian rogue was planting poisons on a Bandit Marauder in Fort Hraggstad Prison. He got rumbled, and having no chance in a straight up fight decided to make a run for it. He got to the top of the stairs where there's a door which you can open and close, so he decided to close it to buy some time for his escape, but the Marauder was too quick. At the same time as he closed the door, the Marauder's kill-cam activated spinning my rogue around. The door then slammed shut - trapping my Argonian's head between door and door frame. All I could see for the last few seconds before respawning was a Nightingale cape and an Argonian tail dangling from a shut door, quivering in its death throes.

Climbed out of Giants Grove and walked to the edge of the map. Black screened, but could still use the menu.

I considered it the equivalent of walking into The Void.

I was crouched a ways away from a dragon who had his back to me so I just started firing arrows. So he flies around and stuff but the funny part was was that he landed literally feet away from my character....looking at me...

Best part was I was 'hidden' so it stared at me but didn't do anything because he certainly couldn't see a white Khajiit with Ebony Mail on crouching in front of it in the snow....
Only time he would see me was when I moved a tad, even then...

I punched Arngeir in the face, & he Ice form'd me off the throat of the world, my character begun to spin ridiculously fast, then I started to...fly (kinda) Then, I suddenly teleported to the ground & died.

A good one for me, I was running from a Dragon on a horse in the Markarth mountains and the dragon's fire killed my horse near a waterfall. It was that one Where there are two big ones near each other and my body got rag dolled off both water falls and luckily I lived through both falls by barely landing in water both times. Thought I was going to splat on the ground both times. Especially the first lol.

At least you weren't on fire anymore.

You know how Ysolda always wants to buy The Bannered Mare from Hulda? Well, I started a bar fight over there by Frenzying some of the guests in the inn, and one of them killed Hulda. Right that moment, Ysolda came running into the building, and took her place behind the counter, after which she took on the role of Hulda. Hulda's body was still laying there, fresh after being killed, and Ysolda waltzes into the place and doesn't hesitate from taking over. Brilliant.

I learned that you could kill people using assorted objects and a few tricks.
My bard character currently kills Thalmor with Drums and various instruments simply due to Telekinesis, Unrelenting Force and Firebolt. Oh the fun, but so difficult to get right.

Though that came back to bite me since Aela managed to get stuck in a wagon that glitched, flew, then killed me....

Very true

I was wandering the snowy wilderness southeast of Winterhold, looking for bandits to kill, and treasure to be had. Minding my own business, for the most part. Suddenly, without warning, I was nearly squashed flat, as a dead horse's corpse came crashing to earth about 3 feet in front of me!!! No rider, no indication of where it had come from. My best guess is that a giant managed to orbit the unfortunate horse someplace else nearby, and I just happened to be where it landed. But I like to thing that he managed to get hold of a Scroll of Icarian Flight...

Also, I was wandering from Solitude southwest for my character's first trip to Markarth. I crossed a river, and happened to run through a pack of mudcrabs. Being rather in a hurry, I decided not to bother with these lowly mudcrabs, and chose to evade and run from them instead of killing... They are quite easy to evade, and are slow pursuers. However, it is generally a good idea to check what you are running TOWARDS. Fleeing from these mighty mudcrabs, I run headlong into a pack of wolves, and simultaneously attract the attention of a nearby sabercat!!! This pack on my heals is now quite dangerous, and much more agile, and I am hard put to keep my hide out of their slavering jaws! I jump off a small cliff in an attempt gain a bigger lead on my pursuers, right into the middle of a pitched battle between a spriggan, black bear, and a necromancer. With these new additions to the frenzied pack on my heels, I continue to flee, attempting to climb a small mountain in hopes that enemy density would be less there. Instead, I manage to attract the loving attention of a Frost Dragon who happened to be hunting the area for a meal. His hunt ended at the same time as my epic flight... Having naturally forgotten to save, my game reloaded me at the gate out of Solitude, where I promptly purchased a nice, safe carriage ride to Markarth!

I got sick and tired of Brynelf trying to recruit me, so I pulled out my fire swords (Tiberius has been boning up one One-Hand... never hurts to be versatile) and becan slicing at him. Then EVERYONE decided they wanted a piece of Brynelf and began attacking him with whatever they had (kind of funny that Balimund, despite being a master smith, carries only a cheesy-looking dagger). Brand-Shei, Modesi, the guards, that meat-seller, probably about a dozen of them. Of course, Brynelf was indestructible, so he was giving more than he was getting, even chopped down an Imperial guard. I finally realized this wasn't going to work and innocent people (many of them characters I liked) were going to die. So Tiberius stepped back and used Voice of the Emperor. Immediately, the brawl stopped and people just went back to their normal business, like nothing had ever happened. Just another ordinary day in Skyrim.

Well, it was the first time I bought a horse...And then realized how useless the things were. Five minutes out of town, after learning how slow and clunky they are, a bear comes from stage left out of the wilderness, and one shots me horse from under me, sending and the horse flying. Horse is dead and I'm pissed about the loss of a 1000 gold investment.
A week later in-game, I fast travel back to a locale because I was feeling lazy...and lo and behold, Butt Stallion was standing there alive and well, looking at me like "Sup?"

Last week, I pickpocketed a bunch of forsworns weapons and just drop it over the edge of a cliff. But I didn't know some of them ended up on a small reachable rock right underneath. Then when I appear and fight them, this one forsworn try to run for his weapon on that rock; which requires him to jump down a little to get it.

He overshot and totally missed the rock!... . It's amazing what the AI would do when you just "nudge" them a little... Ever try dropping diamonds in the middle of a bandit camp?

Oh, gods, I have to try that. I have a character that would do crap like that just to amuse himself, too.

I think one of my best ones was, with a new character, I'm screwin' around kicking a cart full of cabbage around. Someone makes a comment along the lines of, "Don't hurt yourself," and I laugh. Less than ten seconds later, the cart catches on a rock, bounces off my forehead and nearly kills me. Me, being the sort that pushes my luck in videogames, I go kick the cart again immediately and it knocks a cabbage up from under it, the cabbage hits me in the face and shaves off that last couple HP I had left.

Here Lies Menelri
Killed By Rogue Produce
May She Be Smarter In The Next Life

one time i was passing by Whitewatch Tower near Whiterun and bandits attacked it i jumped in and helped the guards to kill the bandits once everything was over one of the guard turned towards me and said " been too long since we've had a good bandit raid " i just smiled shook my head and off i was on the next adventure

When I discovered the horse can sprint, I had a good laugh.

Mine is a Dawnguard one, and not a random moment so much as one line of dialogue that had me keeled over laughing - I'm using the spoiler tag because it involves information about a quest:

I once saw a dragon dive down towards me and fall through the ground, literately disappeared! A few seconds later the dragon it flung out of the ground up into the air, dead. Easiest Dragon Soul I've ever gotten.

After my Battlemage Derik reached a conjuration lvl where he could summon his own Dremora, he gave Sanguine Rose to Erik, thinking of course that two Dremora are better than one. After finding Erik fighting his own Dremora more than once, he took Sanguine Rose back and tried putting it in a display case and this is what happened...http://i1254.photobucket.com/albums/hh611/Trace9569/HPIM1541.jpg

Edit: had to finish my sentance...lol

I did this quest. http://www.uesp.net/wiki/Skyrim:A_Night_To_Remember

That was funny.

I saw a carriage complete with horse fall from the very sky and land intact. I said wow, they don't make wood like this nowadays.

Well today in skyrim i just completed the quest where you had to get the second werewolf totem for hircine and i just left the cave it was in and all of a sudden i heard a dragon and it started to attack my horse (damm dragon) so i fought the dragon and all of sudden bandits arrived and started attacking me, my companion aela was no help ( i think she was fighting the dragon) and when i tried to get back to fighting the dragon even though it flew some distance and i was using some of the trees as cover the dragon killed me.
Another funny thing that happened to me was after i completed the breaking dawn quest and i left the temple i got ambushed by hired thugs after i barely beat them a dragon shows up i almost killed it but when i took cover by some trees i suddenly got glitched in the ground ( i was in the ground up to my waist) and the dragon ate me.

Can't remember my funniest, probably in an older version of this topic. My funniest today.....

So I'm walking in the woods near Riften and I see a red dot. So I start to sneak towards it, the eye is completely open but I don't see anyone there. Then..... a CHICKEN runs out of a bush. Not just any chicken, a chicken with a purple glow and black smoke rising from it. A zombie chicken! Unable to attack me it just walks on by. So I head in the direction it came from, and there is a necromancer. When I kill him I notice he has built a freaky looking altar out of bones and surrounding it are chicken eggs. Then the zombie chicken comes back. Shouldn't something being kept alive by an undead spell turn to ash when the necromancer dies? So now there is this altar made of bones surrounded by chicken eggs that I guess are being laid by a zombie chicken. Maybe that is why it doesn't turn to ash, maybe it was the offspring of an undead chicken and it was born undead and doesn't need a spell to stay alive. Maybe the necromancer was trying to create a zombie chicken army to take over the world.... a horrible idea, but very amusing.

Played this game for hundreds upon hundreds of hours and never saw that before.

Wow, I've never seen nor heard of that before, that is pretty funny. I'm kinda jealous that I've not seen something like that before. :/