The Queen (1968)

Queen is a ribald hour-long documentary about a Miss All-American Beauty contest held in New York in 1967. So what, you say? Well, it happens that all the contestants are male transvestites -- and some of them are real knockouts. Alternately hilarious and depressing, Queen was considered the cutting edge of obscene outrageousness when originally distributed by Grove Press (the publishers of several above-the-counter alternative magazines of the 1960s). Nowadays it's practically kid stuff, thanks to the surfeit of TV tabloids and Fox Network sitcoms.