May 23, 2018 at 10:00 AM EDT
Vintage (3)

The late, great author Philip Roth was not only innovative, he was prolific. He won all of America’s four major literary awards (the Pulitzer, the PEN/Faulkner, the National Book Critics Circle, the National Book Award) and published dozens of works. He is regarded as one of the country’s most important writers, so readers would do well to pick up any of his titles.

Of course, each author has a select few novels that push their way into the cultural conversation more than others. And given that Roth published what would be his final novel back in 2010, there’s a good chance that many people are less intimately familiar with his books than they’d like to admit. No need to expose your dirty little secret to the world, though: A read through any of his three most critical titles will not only aid in educating yourself on one of the foremost authors of our time, it will provide plenty of fodder for insightful discussions about the impacts Roth made on the world.

The big debut: Goodbye, Columbus

Technically this collection is a novella, but who’s counting? Roth published his first stories in The New Yorker, but it was the 1959 publication of this title that took the literary world by storm (he won the National Book Award). Goodbye, Columbus is a collection of six stories musing on American Jewish life at the half-century mark. The titular novella gained the most attention, following Neil Klugman as he works for the public library, lives with his aunt and uncle in a working-class neighborhood of Newark, and meets a monied, sophisticated girl from Radcliffe College.

That, of course, would be Brenda Patimkin, the subject of many a think piece. Brenda’s family lives in Short Hills, with all of the pastels and country clubbing that comes along with it, and Neil begins to muse on the subjects of class and assimilation as he delves deeper into the summer romance.

Like many of his books, Roth received both praise and criticism for Goodbye, Columbus — the latter coming mostly from the Jewish community, rabbis, and even the Anti-Defamation League. Musing on it later in a New Yorker piece, the magazine’s editor David Remnick wrote: “His sin was simple: he’d had the audacity to write about a Jewish kid as being flawed. He had violated the tribal code on Jewish self-exposure.”

The Great American Novel: American Pastoral

Although it may not be his most famous book, this is what won him the Pulitzer prize. (Which, if we’ll remind you, is for works by American writers, about American life). In case this hasn’t become obvious yet, this book is quintessentially American, but in the manner of questioning pretty much everything.

American Pastoral, published in 1997, follows a successful Jewish businessman in New Jersey (sensing a theme here?), whose more conventional middle class live gets completely overturned by the social and political upheaval that was Lyndon B. Johnson’s presidency. His daughter, Mary, sets off a bomb in protest of the Vietnam War, subsequently murdering an innocent bystander. The family is forced into hiding and, as one can imagine, never recovers.

What makes the book so fascinating is that it’s told by a different narrator (Nathan Zuckerman, a frequent alter-ego of Roth’s) as he attends his high school reunion in the 1990s. He pieces together what happens to the family through discussions with classmates, newspaper clippings, and his own impressions.

The controversial one: Portnoy’s Complaint

This explicit novel is not exactly safe for work, but it is the title that sent Roth into the next level of literary stardom. The 1969 book is, essentially, a sexual autobiography. The main character was raised in a strict Jewish household, grows up to be a lawyer, and discovers that he’s been totally repressed in every way. Unfortunately (or fortunately, depending on your point of view), he decides to reverse that repression by all kinds of sexual conquests and then recounting them for us, the reader.

Portnoy’s Complaint is most certainly an acquired taste — beyond the very detailed sexual matters, it’s written in the form of a monologue, which mans that it’s a bit of a stylistically mixed bag. But it’s worth a perusal, as it’s the book that truly made Philip Roth famous, and it sent shockwaves into the book world, the results of which are still being felt today.