If this isn't real-world math, I don't know what is.
http://www.slate.com/articles/arts/culturebox/2013/11/where_s_waldo_a_new_strategy_for_locating_the_missing_man_in_martin_hanford.html
I like what you can do with this around probability and area. It also makes me think about what kids hear/understand when they use and read the word "random." Do they think that Waldo is placed randomly? Why or why not? What would the pages look like if he were to be placed randomly?
I also like that it takes something that looks like it has little order, and uses math to help you see something you wouldn't otherwise be able to notice.