My husband's a professor. He teaches a fairly dry subject at the introductory level (read: huge classes, 200+ people). He's made a practice of sneaking in pop-cultural references just to keep things interesting. It started with Spongebob -- Sozlet would watch it while she was getting ready for school and he was getting ready for work, and he'd start using references to that in examples, quizzes, etc.
We're all kind of tired of Spongebob though (we've seen the old ones 3,000 times each and the new ones suck) and it seems generally over, pop-culture-wise. He's looking for new material -- stuff that these 20-yr-olds would recognize without being dangerous.
For example, when I suggested Obama stuff ("Yes we can," whatever) he said that a) it's too hard to make fun of him and b) he has to stay non-political/ non-partisan.
Last year I gave him LOLcats and he's used that. (Especially in written stuff like exams.)
I just suggested Project Runway ("You may leave the runway," [he brings people up on 'stage' for various participation thingies] "Make it work").
He wanted something a little more macho and I suggested World of Warcraft. I know nothing about it but I see references a lot and seems macho.
Just a selection to give you some ideas.
We're not going for stand-up comedy material here -- I think an element of why this works is that the kids appreciate that their 40-yr-old professor is trying to be hip, even if he looks even nerdier while doing so.