Here are some links to think that made me laugh at some point. Be warned, I have a strange sense of humour.
Sites that are updated with Funny Stuff
Maddox - The Best Page In The Universe - Maddox... he doesn't update very often anymore, but there is plenty of gold to be found here. Maddox tells it like it is... or how it isn't really but in an amusing way. Maddox can get on some peoples wrong side though, so you probably don't want to head over to his site if you are a bit sensitive... or even the tiniest bit sensative. Personally I laugh my arse off. Try this one out as a litmus test Maddox grades childrens' artwork. Personally I was crying I was laughing so hard when I first read this... but then I'm a strange guy.
Strongbad's Email - This is normally quite a good source of entertainment. Cartoon type animations in response to emails. The rest of the site is strangely nowhere near as funny... but you get that. There are also some games here. Look out for Trogdor. Trogdor the Burninator is awesome-O.
Viral Video - Has lots of short videos in the realms of "stupid-sexy-weird-funny". Viral Video also supports Real Player, Microsoft Media Player and Apple's Quicktime players. What is pretty special is how it cycles through a playlist without you having to do anything. You can be in autopilot while is keeps playing short movie clips for you. You can use existing video playlists, or create your own.