In Martin Scorsese’s 2010 documentary about Fran Lebowitz, Public Speaking, Lebowitz explains that news is no longer information. “Facts are what’s important in news,” she says, “but no one is interested in facts anymore.” Eight years later, not only is she right, but facts no longer prove anything, and the truth is open to interpretation.

Fran Lebowitz is usually right. Fran Lebowitz told you so. She is an astute observer and social commentator with an ability to dissect human nature—to pinpoint particular trends and habits, like how we consume, what we value, and how we behave. This is how she maps out society’s downfall. The problem is that by the time we catch up and realize she’s right, it’s too late.

Despite that, even she couldn’t foresee Donald Trump’s victory. But she’s less preoccupied with that mistake than she is with what he’s destroying. And now Lebowitz, who is famous for delivering snap judgments in front of audiences, is getting more questions about politics than she is about her writer’s block.

That knack for observation was present early in her career, when she was writing her opinion column, “I Cover the Waterfront,” for Interview, and then in her two essay collections, Metropolitan Life and Social Studies. And in spite of her “writer’s blockade,” she has made a career out of talking and delivering her opinions on society, politics, and art. Since 1981, she has been writing her famously unfinished novel, Exterior Signs of Wealth. Ever the ironist, for nearly fifteen years Lebowitz has also been working on Progress, a critique of American life and culture. Lebowitz is still a literary humorist operating in more a classic, subtle tradition: she minds other people’s business just as much as Oscar Wilde, James Thurber, Dorothy Parker, and Dawn Powell did.

She spoke to me over the phone, from New York, the day before Toronto elected Doug Ford as premier-designate of Ontario. (Doug Ford, the brother of Rob, mayor of Toronto, 2010–2014, has been compared to Trump for his right-wing, brash, regressive views.) At one point, I had a momentary lapse of reason and brought up her recent “book tour” (by which I meant “speaking tour”). “Believe me, I wish it was a book tour,” she interjected, “because for a book tour, you need a book.”

—Sara Black McCulloch

I. “THERE IS NO REASON WHY PEOPLE SHOULD BE ALLOWED TO MAKE BILLIONS OF DOLLARS.”

THE BELIEVER: Do you think that people in power know how to get away with everything?

FRAN LEBOWITZ: The thing is, most people don’t understand capitalism. My father, in...