The Delights of New York, Fran Lebowitz, and Martin Scorsese’s Laugh

The documentary series “Pretend It’s a City,” now streaming on Netflix, feels like a balm in a wildly shifting world.
Fran Lebowitz
The one thing in New York that doesn’t really change is Fran Lebowitz.Illustration by Joana Avillez

Is there anything more delightful than watching Martin Scorsese enjoy someone? One of the best things about his new documentary series, “Pretend It’s a City,” is getting to see the filmmaker react to his subject, the author and humorist Fran Lebowitz, who is also his good friend. Ten years ago, Scorsese made “Public Speaking,” his first documentary about Lebowitz, which was an ode to a vanishing breed of New York celebrity, as well as a portrait of the city itself. Sitting in a booth at the Waverly Inn, Lebowitz expounded on her various hobbyhorses, including her rejection of technology, her love of talking, and her addiction to smoking. (“The clerk said, ‘Oh, you know, Marlboro Lights, they’re on sale.’ And I thought, Really? Why? . . . They could be a million dollars, I don’t care.”) Now Scorsese and Lebowitz have made a kind of sequel, which comes, in the manner of the hour, as a streaming Netflix series rather than a feature-length film.

Its seven episodes, each of which is centered on a different theme (money, wellness, books), are refreshingly loose, the conversations between Scorsese and Lebowitz often meandering. The show’s only through line is Lebowitz herself, whose slapdash history of New York City is mostly just an occasion to riff. Scorsese’s role is largely limited to explosions of laughter, often heard off camera, and fretful interjections. (His reflexive “Oh, Fran, no!,” as she tells a story about thinking that the falling chandelier at a performance of “The Phantom of the Opera” was real, is a study in empathetic responsiveness.) Though the director is often recognized for his bravura, his modesty—his ability to foreground his interlocutor—is perhaps one of his greatest skills as a filmmaker.

Scorsese loves characters, and his style is to let them reveal themselves through gesture and, especially, through speech. This has been apparent in the vivid voice-over monologues of Robert De Niro’s Travis Bickle, in “Taxi Driver”; Ray Liotta’s Henry Hill, in “Goodfellas”; and Leonardo DiCaprio’s Jordan Belfort, in “The Wolf of Wall Street.” Scorsese’s documentaries, too, often hinge on the portrayal of voluble figures. In my favorite, “American Boy,” from 1978, he interviews his friend Steven Prince, a wild-eyed former road manager and drug addict, marginally known for his minor role as a gun salesman in “Taxi Driver.” Scorsese sometimes interjects, on one occasion requesting that Prince take another stab at telling a story for the camera. (“When you told it to me on the plane, there was a little more sincerity to it,” he says.) Even so, he gives Prince room to weave tales about his colorful life; it’s film as a tour-de-force performance of personality.

Lebowitz needs plenty of room. This will come as no surprise to anyone who is even vaguely familiar with her work, which, in the past four decades, has largely consisted of being Fran Lebowitz: a strong-willed, grumpy, verbose, brilliant woman, who is eager to give her invariably cutting take on anything and everything. The daughter of Jewish parents, Lebowitz grew up in New Jersey and was expelled from her high school for being a bad influence on her peers. (One example: “We had a Halloween party and I came as Fidel Castro,” she has said.) Around 1970, she moved to New York City, where she wrote a column for Andy Warhol’s Interview magazine, and published two acclaimed essay collections—“Metropolitan Life,” in 1978, and “Social Studies,” in 1981—which were full of spot-on observations about contemporary living. I’ve always loved her description of a phone call with a Hollywood agent, who, she noted, sounded “audibly tan.”

Apart from writing one children’s book and the occasional magazine article, Lebowitz has suffered, in recent years, from what she calls a “writer’s blockade.” This has prompted her shift from an actively publishing author to a legendary public wit, who earns her living through speaking engagements. This is excellent work if you can get it, and, as far as I can tell, hardly anyone but Lebowitz has. Former Presidents have pivoted to making money on the lecture circuit, but they had to be President first.

“Making distinctions is my profession, and judging is my profession,” Lebowitz tells Scorsese in the second episode, and, throughout the series, she does so extemporaneously, and with a spectacular self-assuredness in her own tastes. “The kind of snobberies I have,” she says, “has to do with: ‘Do you agree with me about this?’ ” She is a fan of the definitive maxim. (On health: “Your bad habits can kill you . . . but your good habits won’t save you.” On wealth: “There’s only two kinds of people in the world—the kind of people who think there’s such a thing as enough money, and the kind of people who have money.”) She also loves the minor wisecrack; speaking about a child she knew whose parents allowed him to have ice cream for breakfast, she says, “That house to me was like the Marquis de Sade.”

As I sat down to watch, I recalled that, when “Public Speaking” came out, I went to see it at Film Forum, a fifteen-minute stroll from the Waverly Inn. Now Film Forum had been shut for nearly a year, and I was viewing “Pretend It’s a City” from my couch in Brooklyn, feeling far away in more ways than one. “Pretend It’s a City” shows New York as it was when people still left their couches. Most of Lebowitz’s conversations with Scorsese were recorded in late 2019, and are presented alongside clips of public events in which she speaks onstage with other notable interviewers—Spike Lee, Alec Baldwin, Olivia Wilde—and interstitial footage in which she walks the streets of a pre-pandemic Manhattan, in her uniform of cuffed jeans, cowboy boots, and a well-tailored jacket. Her shoulders are squared defensively, and the perma-sulk on her face suggests a preëmptive annoyance with her fellow-man.

Occasionally, as he did in “Public Speaking,” Scorsese inserts archival snippets of musical performances—Marvin Gaye rehearsing “I Want You,” the New York Dolls tearing through “Jet Boy,” as a way of invoking a bygone city. But these touches, while lovely, aren’t enough to make the show particularly compelling visually. That isn’t the point; rather, the point is to hear Lebowitz talk. Her opinions about New York are legion, and a lot of them are what you might expect: tourists who stop in the middle of the street are exasperating; the city is a trial to live in (“Everything in New York is like the ‘Ring’ cycle!”); people are always on their phones and not looking where they’re going; the subway is barely operative and smells bad; the city changes all the time, and, as soon as you finally get used to something, it’s gone.

The one thing in New York that doesn’t really change, it seems, is Lebowitz. The endurance of her infuriating, stubborn, and hilarious self feels like a balm in a wildly shifting world. There is something delicious, too, in hearing her complain—and be unabashedly petty—during a time in which to do so is a faux pas. She almost seems to be kicking New York when it’s already down, and it is exactly what a love letter to the city should look like.

Lebowitz’s New York—well-fed, culturally élite Manhattan—is a particular type of New York, to be sure, and one gets a sense that both she and Scorsese can enjoy recalling (and romanticizing) the city’s grittier, impoverished past thanks to the safety of the perch they’ve long occupied. It is interesting to watch “Pretend It’s a City” alongside the recent documentary series “How To with John Wilson,” on HBO. Wilson, who, at thirty-four, is nearly forty years Lebowitz’s junior, gives viewers an exploratory, lo-fi, collage-style depiction of the city, which includes bare scaffolding in Harlem and his cat’s litter box in his Queens apartment. The footage, despite—or maybe because of—its mundanity, is affecting. Still, there is something to be said for larger-than-life landmarks. “The great thing about Grand Central Station, the reason it’s so beautiful, is because one person built it,” Lebowitz says in the fourth episode. “A building that size now would never be built by a single person. There would not be a single sensibility.” Besides her own, of course. ♦