First one is my favorite : Matrix runs on windows. Listen carefully for some meaningful (real-world universal truth) lines like : "progress bar is moving but remaining time is going up". Its time to upgrade to Ubuntu.
Second one is music remix based on XP error sounds.
Third one is really creative geeky rap video from some "Sniper Twins".
Fourth one is from movie Office Space : Movie based on life of frustrated IT-Software Engineer, really describes life of some my friends : working on weekends, reporting to more than one boss. Somebody come up with that one, good, its old movie though 1996.