If you aren't into the webcomic xkcd because it's too nerdy, here are some entries I think have relatively broad appeal. You don't need to be a programmer or a mathematician to find these amusing:
Lego: That's deep. My only quibble is that the lego house (like grandpa) still exists in our hearts, minds, and imaginations.
Movie Narrative Charts is wonderful (it's better when big). I like the LOTR and Star Wars diagrams, but really like 12 Angry Men as well.
Scary: This sort of thing gets me all the time. Boy Kid was born a month and a half before 9/11/01, so he is the same age as the post-9/11 era. We have project managers at work who are too young for me to have taught them: I stopped teaching before they entered high school. Holy crap!