So you guys like roleplaying? Cool. You guys like stupid shit? That's cool too.
Not necessarily combining the two? Whatever.
The Spoony One (dude who runs the Spoony Experiment) has had this thing going for a while where he recounts his personal roleplaying experiences that were out of the ordinary. He calls it Counter Monkey, after sharing these experiences with people while working in a games shop. Since I haven't roleplayed all that much myself in my day I don't have many myself, but I find this guy's stories so amusing to listen to. They range from extraordinary to peculiar to amusing, and Spoony's natural story telling ability just makes it all better. Check it out at http://countermonkey.com/
My personal favourite is also the longest one on there (it's like a feature film), he was running a Thieves World campaign where his entire original campaign was thrown out the window because one player decided to do something really stupid.
He also has a video on a really unlucky strike of rolls in a SpyCraft game, where everything just goes to shit for his players because nobody can roll over 10.
Oh, oh, and then there's the one with Shadowrun and the squirt guns filled with psychoactive drugs that broke the game!
Go check it out, now!