My advanced art students (meaning they've had at least Art I at the high school level...long story) have just started working on landscape paintings and as an art history tie-in, they're learning about artists of the Hudson River School.
In an article they were to read about artist, Thomas Cole, for homework, they also learned about artists who work on commission and those who exhibit their work in galleries (who, of course, are often one and the same). I thought there was a pretty good discussion in the article about commissioned vs gallery work as a means of self-promotion and so one of the questions on their review sheet was to name the advantages and disadvantages of commissioned work vs gallery work.
A VERY few students could connect this: commissioned work=guaranteed money, but having to paint something that someone else has requested; gallery work=speculation (no guarantee of a sale) but the ability to paint what you want to paint. Most had absolutely no clue.
I also blew them out of the water by asking them to paraphrase a quote by Thomas Cole (told them to use a dictionary if they were unsure of the words) and then explain what he was trying to say about society at the time.
These are generally bright kids in grades 10-12. Who'd have thunk this would have tripped them up so badly? I certainly didn't see it coming!