Literature: Portnoy's Complaint

Portnoy's Complaint: A disorder in which strongly felt ethical and altruistic impulses are perpetually warring with extreme sexual longings, often of a perverse nature...

Portnoy's Complaint (1969) is an American novel by Philip Roth. The novel tells the humorous monologue of Alex Portnoy, a sex-obsessed Jewish youth who confesses his often bizarre sexual encounters to his psychotherapist. Though it was originally banned in several countries due to its explicit content, it is now often ranked among the greatest novels of the 20th century, and is one of Roth's most popular books, along with American Pastoral.
This novel provides examples of:
  • Author Avatar: Roth and Alex Portnoy share a date of birth, a hometown and an ethnic/religious background, so this trope is inescapable.
  • Country Matters: One sexually explicit chapter (hell, they all are) is titled "Cunt Crazy."
  • A Date with Rosie Palms: An entire chapter, "Whacking Off," is dedicated to Alex's experiences with masturbation. In his teenage years, he masturbated at every opportunity, and lived in fear of being caught.
  • Hormone-Addled Teenager: As a teenager, Alex was obsessed with sex and girls, but much to his frustration, he never really grew out of it.
    Day and night, at work and on the street-thirty-three years old and still he is roaming the streets with his eyes popping. A wonder he hasn't been ground to mush by a taxicab, given how he makes his way across the major arteries of Manhattan during the lunch hour. Thirty-three, and still ogling and daydreaming about every girl who crosses her legs opposite him in the subway!
  • Jewish Mother: Combined with Freudian Excuse and probably Oedipus Complex. Alex attributes his sexual disappointments to his overbearing mother.
  • Mattress Tag Gag: Near the end, Alex claims that he's always cruelly punished by the universe for minor transgressions, and imagines that if he's remove a mattress tag, he'd get the electric chair.
    "This is the police speaking. You're surrounded, Portnoy. You better come on out and pay your debt to society." "Up society's ass, Copper!" "Three to come out with those hands of yours up in the air. Mad Dog, or else we come in after you, guns blazing. One." "Blaze, you bastard cop, what do I give a shit? I tore the tag off my mattress-" "Two." "-But at least while I lived, I lived big!"
  • Matzo Fever: Alex tells how in his teenage years, he thought that he has to pretend to be Christian to attract Christian girls. Later, he realized that there's no need for it, because there are plenty of Christian women who are attracted to Jewish men just like him.
  • Only Known By Her Nickname: The Monkey, most notably.
  • Sex Is Evil and I Am Horny: Alex is obsessed with sex, and feels guilty about it.
  • Shiksa Goddess: Alex's girlfriends The Monkey, The Pumpkin and The Pilgrim are this to him.
  • The Shrink: Alex is narrating this entire book to his psychotherapist.
  • Three-Way Sex: Alex has a threesome with the Monkey and an Italian prostitute in Rome, but he finds it more strenuous than sexy.
    I can best describe the state I subsequently entered as one of unrelieved busy-ness. Boy, was I busy! I mean there was just so much to do. You go here and I'll go there- okay, now you go here and I'll go there- all right, now she goes down that way, while I head up this way, and you sort of half turn around on this...