Portnoy's Complaint is the funniest book I've ever read, and possibly the filthiest. My biggest regret is that I didn't read it earlier in life, but who was going to recommend this Jewish tale of masturbatory escapades to an Irish Catholic kid?
The central character, Alexander Portnoy, reviews his wretched Jewish life to his therapist - his masturbatory teen years, his love/hate relationship with his mother with all it's Oedipal complications, his disdain for his whining father, and his myriad of graphic affairs with "shiksas." Roth's use of language while describing Portnoy's sexual escapades makes the scenes hilarious. The scene where Portnoy is trying to pleasure himself while his mother knocks on the bathroom door and tells him not to flush the toilet because she wants to see his number two (she believes he is eating too many french fries after school) is downright brilliant. And, when I told a friend I was reading this novel, he replied, "have you read about the liver?" with a laugh. This novel is surely not for everyone, but if you enjoy dirty, humorous depictions of the human condition, read Portnoy's Complaint by Philip Roth.