Transgressive fiction is a genre of literature which focuses on characters who feel confined by the norms and expectations of society and who break free of those confines in unusual or illicit ways
Without spending too much time elaborating on theories w/r/t transgressive fiction, the above quote is from Wikipedia. Succinct, it offers a broad enough outline to convey the gist of this often ill-defined subset of fiction.
This isn’t a definitive list. It’s also not intended as authoritative. Instead, it’s a list of some transgressive books that have inspired me as a writer—and a person—over the years. Although I should clarify that I don’t love every book on this list. In fact, I find some of them repugnant, their authors appalling, but they’ve still affected me in one way or the other.
If you haven’t read much transgressive fiction, you should do yourself a favor a take a detour into world funny and strange, terrifying, awe-inspiring, and disturbing.
Although this list deals primarily with fiction, I’ve decided to include a few important works of non-fiction and poetry.
How to Talk Dirty and Influence People by Lenny Bruce
(Playboy Publishing, 1965)
Perhaps the most important comedian of the twentieth century, Lenny Bruce introduced satire and social commentary to mainstream comedy. His career started as any other in the 1950s: telling jokes wherever he could—bars, strip clubs, fledgling nightclubs. His career started with a whimper as he told jokes typical of the time. But when he found his voice, he forever changed the face of comedy—and became a target for federal and local law enforcement and puritanical groups intent on preserving the bland discourse of totalitarian 50s America. (more…)