The "Dead Parrot Speech by Margaret Thatcher", based upon the famous Monty Python Sketch illustrates an interesting point about staying in touch with pop culture and using it to connect with one's audience. Simon Hoggart of The Guardian gives a wonderful account of her simply not having the foggiest idea of what this sketch was, and what a touchstone of absurd humor it would be for her listeners. Yes, it went over famously but it's curious that she was so disengaged from Monty Python's entertainment.
As a teacher of middle schoolers I get to keep up with random memes, viral videos and crazy, inappropriate material from shows such as Tosh.0. But these entertainment items are the students' context, and if I'm not in on the joke, I won't be able to effectively communicate with them. Carefully choosing a hook and then making an analogy to the objective of our lesson, or having them describe (on an exit slip/google doc/discussion board) how they think it related can go a long way. And it ups the level of critical thinking.
For example, I begin a class with the picture on the left and ask students, "Why can we relate to this? What is its meaning?" Then after making a list, we move through the related Latin activities, texts, of the lesson and finally I present the last picture, and I ask, "How did the Romans relate to this sculpture? What does it tell us about them and their views?" Getting the interesting responses and moving students from the (sometimes) shallow 21st century one-liner to a lasting, reflective moment can happen.
So Margaret Thatcher had some good advice from her speech-writers. And context is powerful stuff.