Philip Roth, who died Tuesday at 85, was one of the preeminent American literary figures of the 20th and 21st centuries.

Winner of the Pulitzer Prize, the National Book Award and other honors, Roth delved (often with sharp humor) into politics, sex, and Jewish identity and anti-Semitism in his fiction.

Here are five of his best-known and most important books:

  1. “The Plot Against America” (2004)

This prescient alternative historical novel suddenly became part of the conversation during and after the 2016 presidential election. Roth imagines a world in which aviator Charles Lindbergh, an isolationist known for his “America first” anti-war slogan, is elected president and appeases Nazi Germany. A terrific read whatever your politics.

Topping this list of five essential Philip Roth novels: "The Plot Against America."

Topping this list of five essential Philip Roth novels: “The Plot Against America.”

  1. “American Pastoral” (1997)

Roth won the Pulitzer for this novel about homegrown terrorism. The protagonist is Swede Levov, a New Jersey high school athlete who grows up to inherit his father’s glove factory. His American idyll is shattered when his beloved teenage daughter turns radical. Ewan McGregor played Swede in the 2016 film adaptation, with Dakota Fanning as his daughter.

  1. “The Ghost Writer” (1979)

This is the novel in which Roth introduces his alter ego Nathan Zuckerman, who returns in “Zuckerman Unbound” and other works. In “The Ghost Writer,” it’s the 1950s, and Zuckerman is a naïve, budding writer who gets a wakeup call when he meets his literary idol.

  1. “Goodbye, Columbus” (1959)

Roth’s first book got him noticed and then some. Roth, who got a master’s in English from the University of Chicago and taught there in the 1950s, said another professor there, Richard Stern, liked the stories he’d tell about growing up in New Jersey and encouraged him to ” ‘write that, for God’s sake. Write that story.’ It hadn’t occurred to me.” That led to this book about independent-minded Neil Klugman and daddy’s girl Brenda Patimkin, a prototypical “Jewish American princess,” who become lovers. Happy ending not guaranteed.

  1. “Portnoy’s Complaint” (1969)

Made headlines during its time for its frank depiction of masturbation and frustrated sexuality. It’s the work that for many years most defined Roth. The humorous novel is told by “a lust-ridden, mother-addicted young Jewish bachelor” confessing to his analyst.

The humorous novel that for years defined Philip Roth.

The humorous novel that for years defined Philip Roth.