Mid-20th Century Great American Novels About White Men and Their Dicks, Ranked In Order of How Much of an Asshole I Became After Reading Them

7. Kurt Vonnegut, Breakfast of Champions (1973)


Why I read it:

When I was in college I spent a summer working at the library information desk.  I read Kurt Vonnegut’s entire oeuvre in two weeks, for which I earned about $700.

What it’s about:

It’s not really about dicks!  But there is definitely a motif of explaining all the male characters’ penis size.  The book asks you to think about whether that really matters or whether we’re all just self-replicating meat machines and existence is inherently meaningless.

How much of an asshole I was after reading it:

You know, I was actually probably a better person.  Kurt Vonnegut is all about being kind to other people.

6. John Updike, Rabbit, Run (1960)


Why I read it:

After reading Portnoy’s Complaint (see below), I was on the hunt for Great American Novels About White Men and Their Dicks.  Rabbit, Run is one of those (famously!).

What it’s about:

A guy named Harry “Rabbit” Angstrom and his dick.  Unlike most of the protagonists of the books on this list, Rabbit is not a coastal intellectual.  He’s a pissant Pennsylvania kitchen gadget salesman with questionable views on consent. He basically just shits on other people’s lives because he knows he peaked in high school when he was a basketball star.  I’m sure he’s supposed to represent the American white male of the mid-20th century.  


How much of an asshole I was after reading it:

I was a bit grouchy because I thought Rabbit was an asshole and I didn’t like spending time with him.  There is a chapter where he has sex with a woman, and the most interesting part of it is that the woman thinks she’s a good cook, so she boils some hot dogs with carrots for him.  Then he coerces her into unprotected sex, begs her not to have an abortion, and refuses to support her or the kid. That’s not the worst thing he does in the book. I have no doubt there are millions of people like Rabbit out in the world, especially across the interior of America, and many of them voted for Donald Trump.  I am sure they do lead lives of quiet desperation, and I do not want to read about them.

5. John Cheever, Falconer (1977)

Why I read it:

I think all I knew about it was that there was some gay prison sex in it.  I might have learned that from Seinfeld.  I found it for a quarter at a flea market when I was looking for stuff to read, and it seemed like at least the sentences would be well written.

I think I might have owned this edition, I remember the font on the cover.

I think I might have owned this edition, I remember the font on the cover.

What it’s about:

Ye gods, I have no idea.  There’s a college professor who goes to prison, something about drugs or a murder, it doesn’t seem to matter.  There’s some very light innuendo about prison rape and then a consensual gay relationship of sorts, but my recollection is that it was not sexy at all and I just didn’t connect with it whatsoever.

How much of an asshole I was after reading it:

I was pretty indifferent to it.

4. Joseph Heller, Something Happened (1974)


Why I read it:

Another flea market find.  In Milan, of all places. I had kind of liked Catch-22--not nearly as much as I had tried to like Catch-22, which I now absolutely loathe--so I figured for fifty cents it was worth a shot.

What it’s about:

A guy who returns from WW2, gets a pretty good office job, and ruminates about his past...and his dick.


How much of an asshole I was after reading it:

Mostly I was just depressed and, somehow, also inspired by it. But I think I was a bit of an asshole for several years telling people that Something Happened was one of the greatest novels ever written and way, way better than Catch-22. As I get older I’m less impressed by deeply unhappy works of art, and I think by pushing this book on people (although I’m sure I didn’t convince anyone to read it) I only revealed the thinness of my taste.

3. Ayn Rand, The Fountainhead (1943)

Why I read it:

In 10th grade a few of my classmates were passing around a copy.  The other guitarist in my band--I was super serious about my band, and it was indeed my band--kept shouting “you’re Peter Keating” at me, and I figured that was probably an insult and I should figure out what it meant.

What it’s about:

There is a guy, Howard Roark, who is an architect and a rugged modern individualist (in the vein of every Ayn Rand hero, as I now know) who won’t ever compromise his art in the name of socialist conformity.  He has a doppelganger, Peter Keating, who does what’s popular and gets famous but secretly wants to be like Howard Roark. Howard Roark doesn’t think or talk about his dick a lot, but at one point he does rape a woman to solve her problems!

How much of an asshole I was after reading it:

A raging asshole for a few weeks, but I never joined the Republican Party.  I briefly kicked the guitarist out of the band, and then we made up. I became obsessed with truth and purity and individualism, until I realized that The Fountainhead was complete horseshit.  But it took a solid 10 years for me to grasp that I was deeply, deeply Peter Keating, as was everyone else, and that it was ok.


The Fountainhead, like all of Rand’s works, is basically a straw-man argument against socialism, in which she divides the world between, in the parlance of modern fascists, the Donald Trumps of the world and the beta-cucks. If your view of Donald Trump is that he is a self-made industrialist who builds beautiful buildings, and anyone who doesn’t care for him is a socialist beta-cuck, then congratulations, you have manifested a world I previously dismissed as irrelevant even as an artistic thought experiment. You got me!

2. Vladimir Nabokov, Lolita (1955)


Why I read it:

I was 12 or 13 and didn’t know how to find pornography (the internet was still kind of new, and I was naive). So I went in search of books about sex.

What it’s about:

As an educated person, I should tell you it’s about the nature of desire and the beauty of language. It is also very much about a dude who fucks kids. It’s written in first person and it is 100% about how badly this dude wants to fuck kids, and he does not apologize for it—it’s a celebration of his desire.

How much of an asshole I was after reading it:

I understand  how  they could make a movie of  Lolita . I don’t understand how it could be any good, and although I love Stanley Kubrick I’ve never had the slightest urge to watch this movie.  Lolita  is the most literary novel I’ve ever read; the whole appeal is that it’s so much about language that you accept the linguistic artifice placed over one of the most morally repugnant human acts. A movie version of  Lolita  can’t play that trick. I’m sure Peter Sellers plays a very witty pedophile.

I understand how they could make a movie of Lolita. I don’t understand how it could be any good, and although I love Stanley Kubrick I’ve never had the slightest urge to watch this movie. Lolita is the most literary novel I’ve ever read; the whole appeal is that it’s so much about language that you accept the linguistic artifice placed over one of the most morally repugnant human acts. A movie version of Lolita can’t play that trick. I’m sure Peter Sellers plays a very witty pedophile.

I don’t know--Mom, how much of an asshole was I from 1998 to 2012 or so?

:::silence:::

I think the big problem was that I was so fully able to buy what Nabokov was selling--the joke, of sorts, that the book was about this taboo subject, but it was really about something else. Like the emperor’s new clothes, “worthy” people can see that Lolita is about language, not fucking kids.  And to be fair, Lolita is probably the most beautifully written book I’ve ever read.  

Looking back, I’m struck by the level of privilege it takes for a person to write a book like that and be celebrated for it.  I mean, can you imagine a black woman writing LolitaLolita seduces you into accepting its premise, engaging on the author’s terms, only because those terms--the central term, that entitled white male penile navel-gazing is the appropriate medium of discourse for celebration of linguistic artistry--can feel so normal.  Nabokov seems to want us to think that because he has so mastered the medium of white male penile navel-gazing, he can tackle even the most taboo subjects in that medium, thus proving that skillful writing conquers any and all subject matter taboos. And to some extent that might be true, but Nabokov has also illustrated for us the nature of entitlement: the tilting of critical thought on an expressive medium such that sins viewed as unforgivable in other contexts can be forgiven and even celebrated due to the artist’s inherent worthiness.

It’s really hard to imagine anyone but a white man writing Lolita because any other perspective (even if it were the same words, written by an Other) would force so many questions and distract from the linguistic artifice. If a black woman were writing Lolita, we would not and could not read it as being about about language and desire and comedy, because we could only see it as a commentary on white maleness and entitlement and rape. (Literally, Act 3 of the book concerns a sort of battle of wits between two pedophiles over possession of a young girl. It’s literally a story about child sex trafficking that is meant to be read comically because the adversaries are very well read. There is pathos to it, but not really for the girl. By contrast, consider Precious, Based on the Novel ‘Push’ by Sapphire. The movie (I’m less familiar with the book) can be read comically, and can be read through the constraints of its medium, but I’ve never heard it argued that Precious is not about it’s top-level plot or that it fails to empathize with its abused child character. Audiences would not accept that conceit.)

Critics, and to a lesser extent readers in general, allow only white males to be read from a socially neutral perspective. This is true of Nabokov as well as his protagonists.


Lolita led me towards a long-unquestioned, unarticulated worldview of “because I’m a white man and an artist, I get to do this.” And the result was, yes, being a raging asshole to people, but also going to music school for seven years to compose super artsy shit nobody liked.

1. Philip Roth, Portnoy’s Complaint (1969)


Why I read it:

I saw it mentioned in articles and such as a very funny book.

What it’s about:

A Jew, his penis, and his mother.


How much of an asshole I was after reading it:

Immediately after reading Portnoy’s Complaint, I was probably less of an asshole than I had been weeks earlier.  And that’s because until I read it at the age of 14 or so, I’d never read a novel that spoke to me in certain very particular ways that this book did.  By particular ways, I mean the book was about another person who, like me, was:

  • Obsessed with sex;

  • Being pressured by my parents to embody certain ideals (particularly through academic success and social standing);

  • Desperate for the catharsis of transgressive comedy; and

  • Wanting to be a good person and feeling conflicted in light of the foregoing.

Portnoy’s Complaint was the first book I ever read that made me feel less alone in the world.  What’s funny to me about that is that all through school, they make you read books about kids your age, and I’m sure that the point of that is you’re supposed to relate to them because they’re kids with kid problems and they look like you or whatever.  But that’s crazy--most books about kids that are taught as literature are about orphans who, freed from the constraints of, you know, having parents, get to go on cool adventures. I certainly enjoyed reading Harry Potter and Huckleberry Finn, but even though I was having a pretty tough time emotionally when I read those books and felt like nobody understood me, those books did nothing for me on an emotional level.  Even Catcher in the Rye, which is assigned in school specifically because so many kids connect to it that way and feel less alone, did nothing for me.  (I never felt like adults were “phony,” and I just thought Holden Caulfield needed to stop whining and be nice to people.)


Reading Portnoy’s Complaint blew my mind.  Oh, other people’s parents put tons of pressure on them to succeed in school and they feel emotionally dominated?  Other people masturbate all the time, in weird places and onto random objects? You can maybe feel that way and do those things and still be a good person—or maybe not?  Brain. Exploded. Whenever anyone dreams of becoming an artist, they dream of my reaction to Portnoy’s Complaint as a teenager.  That is why people make art.  It is the optimal result.


Also there is a fair amount of sex in Portnoy’s Complaint and I jerked off to it.


The problem was that I wanted more.  I wanted every book to be the next Portnoy’s Complaint for me, and I was never satisfied.  I decided that I couldn’t just wait for art to speak to me like that, I had to go out and make my art and tell my story, and then I’d tell other people they weren’t alone, and I’d be loved and celebrated.  


I became an artist because of Portnoy’s Complaint.  And because I connected my artistry and ambition so strongly to Portnoy’s Complaint, I believed that re-hashing the themes and even the plot of Portnoy’s Complaint--the Oedipal Complex, the pressure, the penises--was an acceptable way for me to be an artist. 

(Sure, I read other books by Philip Roth and I really liked some of them, but as a teenager I did not care why all of those other books were so different from Portnoy’s Complaint or what the literary marketplace might think about other writers re-hashing Portnoy’s Complaint. Only later did I learn that Philip Roth wrote Portnoy’s Complaint, which like most of his works is semi-autobiographical, only after one of the book’s major inspirations died in a car crash and he felt free to write about her, and generally his fiction featured a number of real people he knew and people were upset with him about it throughout his life.  Also, he moved on to other subjects, because he wasn’t a hack. It also took me way too long to realize that these days white dudes who write about their dicks work in television where it is more popular and socially acceptable.)


So, at some point in my 20s, I wrote my own Portnoy’s Complaint.  I think I captured the tone and energy of Portnoy’s Complaint pretty well and I modernized it a bit.  It was certainly my own work. I just wanted to write that book, but more so, and more about me.  So I did. It was very cathartic. And before I sent it to my agent, I sent it to my family to make sure they were ok with me publishing it.  They were not. They were upset.  


That was the end of that.  After the debacle surrounding Portnoy’s 2 (not the real title), I decided to take a step back and ask myself why I had ever considered it might be ok to write that book, even if I fictionalized events and whatever.  What about myself and where I saw myself in society made it ok to be a person who would write and publish a book about myself, my dick, my mother, and just how hard it is to be an upper middle class white boy who is expected to do well in school.  Yeesh.


I mean, it was hard.  My childhood was difficult at times, as are most peoples’ childhoods.  The fact that I wasn’t sexually abused or starving doesn’t mean you can write off the feelings I felt about my relatively less dramatic problems.  And so, to this day, the only book I’ve written since Portnoy’s 2 is a stick-figure graphic novel called People Who Hurt Me, a mostly tongue-in-cheek series of vignettes about petty injustices from my childhood, including myself and some of the shitty things I did to people.  People Who Hurt Me feels a lot more true to myself than Portnoy’s 2 ever did, and was fun to write.  There is one copy of it, in a closet somewhere, and I read it about once every three years, and I laugh, and I put it back.


When I think about how much of a raging asshole I became after reading Portnoy’s Complaint, I think about the difference between those two books and the work I had to do to be the person who would write People Who Hurt Me and stuff it in a closet, instead of the guy who would write Portnoy’s 2 and try to get it published.  


I don’t blame Portnoy’s Complaint for that. It’s a great book, you should read it. Very funny.