Recently, I was practicing reading with my six-year-old when we got into a discussion of whether you can start a sentence with the word “and.” I was reminded of a line from Philip Roth, who died this week at eighty-five, from the 1998 novel I Married a Communist. The narrator is remembering his childhood love of Norman Corwin’s radio dramas, a staple of Popular Front culture. He recalls that they were his first sense of what storytelling should be, ending with the aside: “And taught me, contrary to what my teachers insisted, that I could begin a sentence with ‘and.’” My son took a while to get it, then exploded with joy. “Because that sentence starts with ‘and!’” It was delightful: his first Roth joke. Breaking a fake grammatical rule might seem pretty mild on the scale of Roth’s subversions, but it seemed appropriate. Throughout his five-decade career, Roth held to the insistence that the more a person or a culture insisted on a rule, the more nonsensical it likely was.

Roth’s early works attracted attention for their focus on the particularities of his world as a youth: the Popular Front, baseball, the war, and the fine distinctions among those Jewish immigrants of various levels of assimilation and middle-class aspirations. In the thirtieth anniversary edition of his first book, the short-story collection, Goodbye Columbus, he remembered:

In the beginning it amazed him [Roth] that any literate audience could seriously be interested in his story of tribal secrets, in what he knew, as a child of his neighborhood, about the rites and taboos of his clan — about their aversions, their aspirations, their fears of deviance and defection, their embarrassments and ideas of success.