How Don Draper Would Sell Philip Roth’s ‘Portnoy’s Complaint’


A while ago I made an educated guess that this season of Mad Men would feature one or two books that came out in 1969. The Godfather, Kurt Vonnegut, and Margaret Atwood could all still show up in this two-part final season of our favorite show about horrible men in nice suits. Yet those other titles would just be an extra-nice surprise, as last night’s episode featured Don on his couch, reading the book I most expected to see: Portnoy’s Complaint by Philip Roth.

This season of Mad Men is all about change and invention. Most of those new things, however, seem to manifest in pretty bad ways; Don is frozen by doubt and addiction, Roger’s daughter is off with a bunch of hippies, and we haven’t yet seen Bob Benson and his amazing shorts. But it is 1969, the year that is often cited as the one when the cultural landscape dramatically shifted in America, and Roth’s novel was a big part of that.

The thing about Portnoy’s Complaint is that, unlike some books we’ve seen Don reading, like Dante’s Inferno, there isn’t an obvious meaning to Don’s choice of reading, unless you want to get into the mommy/sex issues that both Don and Roth’s most famous character have. It’s difficult to find an allegory in Don opening up Portnoy’s, but a book about a descent into hell, that’s something we can understand.

Still, I got to thinking: what if Sterling Cooper & Partners were contacted by the people at Random House in 1969, and were asked to help market this book? Obviously it isn’t an airline company, Chevy, or some old American brand that needs a fresh new spin, but it’s amusing to imagine what Don would come up with if the partners assigned him the Portnoy’s Complaint account. Below, an attempt to do just that.

On synopsis:

This isn’t a book. This is a complaint. It’s a man, a Jewish man, one of the Chosen People, doing what comes naturally to him. He sits on Dr. Spielvogel’s couch, and he doesn’t talk things out — he weaves a tapestry. People hurt him: his mother, she drives him crazy, drives him to other women that aren’t her; women, to Portnoy, are the root of all pleasure and all pain. He complains about that, that’s what he does, because that’s who he is.

On the cover:

It’s yellow. Yellow is gutless. At first glance, the consumer is taken in by the color; they want to know what’s in between that yellow. But then they look at the title, written in a variant of Caslon Bold. What is Portnoy complaining about? Is it a diet book? A self-help book? Then they open it, flip around a few pages; “I tear off my pants, furiously,” they read. They look around to see if anybody is watching them read. Nobody is, so they continue: “I grab that battered battering ram to freedom, my adolescent cock, even as my mother begins to call from the outside door.” Is this smut? Is this high art? No — it’s yellow.

Ideas for the author bio:

Abraham, Moses, Isaac — you know them from your Sunday school. They were Jews. Did you know Jesus was a Jew? Great men, holy men. Philip Roth is also a Jew. Although he isn’t from Galilee, and he’s no carpenter; he’s from New Jersey. Can you see New Jersey from your window? Of course you can. New Jersey is American. Philip Roth is an American Jew.


“You wanted an excuse to never eat liver again; Portnoy’s Complaint is that excuse.”

“Women. Am I right? That’s Portnoy’s Complaint.”

Portnoy’s Complaint: as American as Jesus.”