A very amusing post on Gossip Girl at The Millions, though I question Garth Risk Hallberg's assertion that GG is less of a "cultural touchstone" for the generation currently in college than it is for the thirty-something set.
I also used Gossip Girl as a sort of pedagogic panacea this summer, when I conducted a mini-course at a summer camp for high schoolers. It worked remarkably well, although, like Garth, I have never seen an episode (and unlike Garth, I could not have named with such precision any character from the show). If attention flagged, I would throw in a reference to Gossip Girl, usually something vague and referring to its popularity.
The most amusing translation of a literary reference into a pop cultural reference that I encountered as an undergraduate was in a course I took my freshman year on the Romantic poets. Our professor re-worked the Shelley-Wordsworth generational battle (best expressed in the very direct Shelley poem "To Wordsworth") as a series of cartoon strips replacing Shelley with the rapper Nas and Wordsworth with Jay-Z. (Speaking of Jay-Z, has anyone figured out yet if the Brits call him "Jay-Zed" or not?) The professor promised us a follow-up series starring Byron as Puff Daddy, but I don't think she ever got around to that one.