I have a number of werewolf mods on my file since i don't have the funds to get Dawnguard and its perk tree. Three of those mods are Scent of the Wolf (so wolves don't attack the player), Godly Werewolf (since I rarely even use the transformation), and one other mod that spawns wild werewolves (I forget the name).
I was exploring around the Riften area when I ran into a wild werewolf and had the fun idea to try the Wabbajack on it. I quicksaved the game before, and used it to turn the werewolf into a rabbit. I had a quick laugh and reloaded the save just to encounter a lag spike before seeing my character flying through the air. Turns out the werewolf stayed hostile after loading the save and my Godly mod worked against me. I almost got stuck in an infinite loop of death and my last save was hours before. I eventually was able to console command the noclip and took care of the werewolf. The Wabbajack now lies buried in Whiterun

And once, I came out of a cave. No big deal right? WRONG! Everything was blue and I couldn't see anything, except for a large black shape that was Shadowmere. So, I got on Shadowmere and it looked like we were falling so I got off him and it turns out we were falling. I had to load the game because I had no idea what had just occured.

Alduin World Eater

And once, I came out of a cave. No big deal right? WRONG! Everything was blue and I couldn't see anything, except for a large black shape that was Shadowmere. So, I got on Shadowmere and it looked like we were falling so I got off him and it turns out we were falling. I had to load the game because I had no idea what had just occured.

Revenge for killing Lidya

I suppose so. I never liked Lydia though. I really like Kharjo, though. 

But he died when my dad was around and I didn't want him to know that I have a crush on a Skyrim character. 

I had the werewolf mod overhaul, and so I made it to where I would transform every full moon. Well, I was doing Season Unending, and the full moon had already passed. Or so I thought. I guess full moons last for more than one night? I don't know, but I transformed in front of everybody! I got a thousand gold in every hold and the blades and Greybeards remained hostile.

I had to load an earlier version and wait out the transformation. It was hilarious!

Styorngolkiir

Let's be honest. As great as The Elder Scrolls is (I personally played only one, but I've seen game footage of another) you sometimes can't help but to laugh.  This thread is ment to be for any Elder Scrolls game, as long as it will make us all laugh out loud! 

Their have been a lot of funny moments. I have some hilarious screenshots that I took on PC, so I'll just show you them:

http://s1333.photobucket.com/user/MegalicaTheArtist/media/2014-03-22_00127_zpsnrkg3rib.jpg.html

http://s1333.photobucket.com/user/MegalicaTheArtist/media/2014-03-23_00006_zpsgf9zvmpy.jpg.html

http://s1333.photobucket.com/user/MegalicaTheArtist/media/2014-03-23_00023_zpsn8a9yvie.jpg.html

http://s1333.photobucket.com/user/MegalicaTheArtist/media/2014-03-23_00026_zpsslxcowwj.jpg.html

The funniest one:

http://s1333.photobucket.com/user/MegalicaTheArtist/media/2014-03-23_00047_zpsrazjs3yp.jpg.html

And finally:

http://s1333.photobucket.com/user/MegalicaTheArtist/media/2014-03-23_00083_zpsdkvwxyyq.jpg.html

So, so many quests all over the damn place. I try to be good and stick to one quest but while going about it, I get shoved into 3 others, literally.

So I'm doing the quest "In My Time of Need" I choose to help Saadia, go through the dungeon and all that. Get to the Red Guard leader (They are all the same and voiced by the same actor...) and he convinces me to help catch her instead. Need to head to whiterun and lure her to the stables. I remember she stays at the bannered mare. Go inside and I can't recall how I get to talking to this guy "Sam" but he challenges me to a drinking game and I decide seems easy enough and if I beat him then I get some staff.

2 drinks for him and 3-4 for me and I end up passing out and waking up in a Maraketh temple having apparently fondled one of the naked statues. So I get kicked out of there. Went towards the gates of the city to leave and stuff goes down in the marketplace, woman got killed and this guy just goes crazy trying to kill everyone, I step behind him and perform a killmove in slomo stabbing him in the back and the scuffle ends. Then get approached by some other guy and told to meet him at the temple of talos, I'm curious so I do and he goes on to tell me about the forsworn stuff and to help him find info on the murdered woman and the man who did it.
Accept the new quest, walk out and down the path, past some doors and get stopped by another man asking me if I've seen anyone go in and out of the house he's standing next to, I say no and then offer him my help. He tells me I can follow him inside and watch his back.

So I follow him in, the house is dark and foggy.. dank? Sure I'll go with that. Weird sounds are heard and he keeps running off hoping to catch someone in the act, we get to a door and it's locked and requires a key, crap starts flying everywhere and he hauls ass back to the front door. This loud voice tells us we have to fight and one of us has to die in order to leave, obviously I'm the better fighter so I win, all the while stuff is still flying around the house. Once he dies everything stops and I'm told to go to the celler and in  the wall is a hole to a cave, basically in there is an alter to Molag Bal, the creator of vampires and in Morrowind know as the "King of Rape" so I'm preparing my anus here. In short he tells me he just wants me to first free and then trap a guy that has been hurting his ego, because he's been desecrating his altar, I expected a bit more from the king of rape to be honest.

ALL that from just trying to complete one quest in Whiterun, FML.

Obligatory humorous unrelated picture
 

I have plenty other stories

I've had plenty of funny moments in Skyrim, a couple stemming from the odd behaviour of Jenassa. There I was, sneaking through a Draugr-infested tomb, with no enemies detected... when suddenly, 'I'll see you burn!' I hear her roar. My character, her loyal husband, spins around, weapons drawn, ready to defend her against the enemy... which turns out to be a spear trap. Which she triggered. And which is now on the receiving end of several of her fiery combat phrases - which she continues to spout at it until (my Dragonborn having been distracted by his wife's odd behaviour) a Draugr Deathlord ambushes them both and gives her something... less inanimate to yell at.

Then there was the time I encountered an Orc (he was just called 'Orc,' so I assume it was a random encounter) in the Bannered Mare who, without warning, picked a fight with my character. Now, I'm something of an RPer, so when I go into inns, I often put my character into normal clothes, which on this occasion I had done. Unarmoured, and afraid to fight the guy because this character is a destruction mage and with my terrible aim I would almost certainly hit an innocent civilian - I run helplessly around the inn hoping someone will come to my rescue until my companion, Onmund, zaps the guy with chain lightning... which kills him, but, being chain lightning, strikes an innocent civilian too. 

'You have committed crimes against Skyrim and her people!' the guards shout, as they pour in through the door of the inn.

I pay off my bounty and dismiss Onmund for a while.

I once turned into a werewolf I became this weird human werewolf thing with a greatsword. It's fucking creepy. 

I found this hysterical for some reason: I enchanted a claymore with a sigil in Oblivion: Iron claymore with a Descendant sigil. I only enchanted it to help me in the arena. Guess what happened on the first fight? I OHK'd the dude.

(OHK means one hit kill)

 Then after that, I decided to hone my magic, and flamed my competition. When I hit them with the claymore after burning them, they flew up 3 feet into the air!

In Riften a youtuber known as the Scatsbury (he is better than most youtubers, he just barely uploads) was cornered by a guard in some peasant's house, who began a mantra of "You're not supposed to be in here. You're not supposed to be in here. You're not supposed to be in here. You're not supposed to be in here. You're not supposed to be in here. You're not supposed to be in here. You're not --" *death gurgle*. This moment went down in Scatsbury history.