Yes -this has come up before - a teacher at Stanton College Prep School in Florida had some of the same issues as you did, and we asked him how it all worked out. His answer was so great that I'm just going to reprint it in its entirety: There are any number of reasons that we wanted to produce Urinetown" - the excitement of mounting a new piece that hadn't previously been produced by anyone else in our town, the vocal and dramatic challenges that the show would pose to our students, the simple sick, twisted fun of it all ... We were particularly interested in the show from an academic standpoint, because "Urinetown"'s indebtedness to the works of Kurt Weill and Bertolt Brecht (not to mention Kander and Ebb, Leonard Bernstein, and Marc Blitzstein) opened up terrific avenues for classroom lessons on Epic Theater. Our advanced classes benefited enormously from this chance to see theatrical theory put into practice. Of course, the title is a little off-putting. Our principal was apprehensive about the show at first, but after discussing it with us, she let us proceed, ultimately telling us after viewing a dress rehearsal that now she didn't understand why she had ever worried about it. Our district superintendent, a former band director, congratulated us for doing such a good job with such a risky piece, and told us that he was proud of the way that we had represented the school system. While simply doing the show was a phenomenal experience - one of the best we've ever had in my twenty-one years at this school - it was even more exciting that we were invited to present our show as a mainstage production at the 2006 Florida State Thespian Festival, where we completely packed a 1,400-seat theater for two performances. The day after we went on, our kids wore urine-yellow T-shirts identifying them as "Urinetown" cast and crew, and they were barraged with compliments from total strangers all day long. I loved every minute of working on this show, and I think that my co-director, colleagues and students would agree that it was the most fun that we have ever had working hard! Jeff More on this production in a great article here. Hope this helps, and if you have more specific concerns, please feel free to address them here - we'd love to help!