As a student, the concept of doing a show that I enjoy enough and would actually pay to go see is about as likely as owning a pet unicorn, which would be awesome. Which is why I do the job not to be entertained, but to work with great people, as seems to be the consensus here, as well as dream of a day in the distant future when the shows I do will be consistently something to be proud of.
That said, I have to admit I'm often proud of the low budget activism shows i've done (especially prevelent in the university setting, I would think), because everyone else involved is so passionate about the message, it's hard not to care a bit. I've done a number of these "statement making" shows for free or as favors in addition to my regular workload because I think experimental, community, political, cultural, etc etc theatre is really important from a society point of view and what have you. Plus, it's nice to get shaken up out of that stage manager's apathy once in a while. Though I have to admit.. if I weren't managing it, I probably wouldn't go myself. And I'd rather do A Streetcar Named Desire anyday.
But to andswer the question itself, no, I've never done any theatre that made me squirm per se, but I have done a fair amount of "compelling/ controversial theatre" as well, and I've particularly enjoyed watching the "white heads" in the audience squirm from the booth.