If you think Jacques Derrida's writing is confusing, wait 'til you get your hands on Joyce's nigh incomprehensible dreamscape, Finnegans Wake (yup, there's no apostrophe). This novel's stream-of-consciousness style builds layers upon layers upon layers of language games into every single sentence, and has a reputation for being the most difficult book ever written in English. Now that's one for the Guinness Book of Records.
So why tackle it? Well, it's hard to think of any other text that'll give you such a clear illustration of language's infinite differences and deferrals. James Joyce's Ulysses comes close (he just had to go for all the prizes), and some of Virginia Woolf's novels do too, but Finnegans Wake is really the cream of the crop.
A couple of questions to keep in mind: how do you even start to try to make sense of the text? By letting the "free-play" of the language flow over you, or by digging through dictionaries to follow Joyce's etymological tracks?
And here's a fun one for a role-play: what might Lacan say about the novel's portrayal of unconscious language activity?