If there was a patron saint of defensive pessimism it should be David Rakoff, although as a secular gay Jewish man selection for beatification would be a long shot.
In his last collection of essays he writes about the internet bubble, visiting Disney's House of Tomorrow, his failed movie career, the forbidden thrill of eating pork, the depressing experience of editing a fiction contest for first time novelists, and his cancer treatment. His sarcastic self-depreciating and sometimes self-pitying humor can get a little tiresome at times, but his entirely reasonable brutal review of the Broadway show Rent could be used to teach essay writing classes.