Warhol's Gold Marilyn comes off as a lot gutsier when students know a little about Byzantine icons.
This isn't to say that students must have a full Janson's-textbook-worth of art historical knowledge to be able to appreciate irony and recontextualization in contemporary art. Kehinde Wiley's portraits of African-American youth in heroic poses, subvert Western tradition of representation in a way that's clear enough to adolescents. A teenager doesn't necessarily need to know about Salon painting to know that it's atypical for African-American youth to be represented on a field of fluer de lis.
Still, though - it's been over a decade since mainstream hip hop became the glammy, fashion-conscious, ultraconsumerist pop culture that it is now.
This image of Biggie Smalls is so glammy! That's completely out of character for hip hop...
Oh, wait.
As someone whose goal is to teach art history and studio art to high schoolers and/or middle schoolers, I try to keep an eye out for images of contemporary art that straddle the "high and low" divide, that use imagery so well-known to adolescents that the irony of their appropriation would be clear to everyone without needing to go back and explain what artwork the contemporary artist was riffing off of.
I've recently found a great example, which was posted online about a month and a half ago:
It's safe to assume that, at the very least, students have seen the Emanuel Leutze painting Washington Crossing the Delaware (1851) in a social studies textbook. They've probably seen it parodied in old Bugs Bunny cartoons. It's an ubiquitous piece of American culture.
And now it's been appropriated by the art collective When Art Imitates Life:
Yes, that IS the Wu-Tang Clan crossing the Delaware River, with ninja manning the oars.
This image is ridiculous. And it's awesome. It would be instantly recognized as the parody/appropriation/recontextualization/self-aggrandizement that it is, and could be used as a really great starting point for a discussion of other ironic appropriation of older forms (like Warhol and Wiley), or a discussion about how heroes are presented, or even about who gets to be called a hero.
My only concern is whether adolescent students consider Wu-Tang to be at all relevant anymore. These kids today, with their hippin' and their hoppin', they don't understand the classics like "Protect Yo' Neck."