Fran Lebowitz and Martin Scorsese declare their love for New York and each other in Pretend It’s A City

Photo: Netflix

Martin Scorsese laughs with his whole body, consumed by an ebullience that manifests in slapped knees and one moment where it seems like he might actually fall off his chair in delight. His glee is the soundtrack to Pretend It’s A City, a reunion with his close friend Fran Lebowitz after their 2010 HBO Documentary Films collaboration Public Speaking. The new docuseries is punctuated by Scorsese’s giggles and guffaws; more than once, closed captions pop up as “Martin laughing” and “Martin continues laughing.” So much of the joy in watching comes from the pure quality of Scorsese’s reactions to Lebowitz, a figure who’s remained singularly herself for the past five decades and whose animated mannerisms, precise opinions, and rambling stories are given center stage here—for better and worse.

Pretend It’s A City is a very niche project, shaped by Lebowitz’s nostalgia toward New York City “back then” and her acidic analysis of contemporary life, and it’s difficult to tell to whom this would appeal outside of Lebowitz and Scorsese fans. For who else would be so tickled by Lebowitz and Scorsese swapping stories about Cary Grant and the 1963 film The Leopard, or trading tips about how best to avoid walking through Times Square, or discussing their experiences on the set of The Wolf Of Wall Street? Not everything has to be for everyone, but even given that warning, Pretend It’s A City is equally disinterested in attracting unfamiliar viewers as it is tempering Lebowitz, who offers bluntly unequivocal thoughts on topics like gay rights, the #MeToo movement, sports, and climate change. When an audience member at one of her speaking engagements asks what she thinks of our time of “suffocating political correctness,” Lebowitz’s deadpan reply of “I’m breathing fine” is effectively succinct. And yes, it makes Scorsese laugh quite a bit.

The seven half-hour installments of Pretend It’s A City provide viewers with an opportunity to live vicariously through Lebowitz’s determined stride around New York, Scorsese’s browsing of library books, and their lengthy conversations over coffee at The Players club. Several episodes are named after NYC departments or institutions, including “Cultural Affairs” and “Library Services,” and they variously explore Lebowitz’s exasperations, praise, or memories related to each theme. The figure of the New York City curmudgeon has existed in pop culture for a long time, and Lebowitz bears that mantle with her signature bold glasses, middle-parted hair, and bespoke men’s suit jackets and overcoat. After being kicked out of high school, Lebowitz moved from New Jersey to the city, where she worked various odd jobs—house cleaner, cab driver—as she also began a writing career. First as a film critic and then as a columnist, Lebowitz wrote for Andy Warhol’s Interview magazine for 11 years, and then found success with two books of essays: 1978’s Metropolitan Life and 1981’s Social Studies. That fame landed her on various talk shows for decades to come, and although Lebowitz’s decades-long writer’s block has become a common subject of her own self-deprecation, she has maintained a career as a public speaker and public figure.

In speaking with Alec Baldwin, she shares how her mother told her, “Don’t be funny around boys”—advice she promptly ignored. She pleases David Letterman with her description of smoking as “It’s my hobby, if not my profession,” and then gets major laughs from the studio audience by saying her days are filled with “smoking and plotting revenge.” She argues with Spike Lee about whether athletes can be artists, with her vehement disregard of professional sports making Lee more and more irritated before she casually mentions having attended the Fight of the Century between Muhammad Ali and Joe Frazier in 1971. She charms Olivia Wilde with her thoughts on social media, which is that she doesn’t use it—Lebowitz doesn’t own a cell phone or a computer—but that she can’t question the emotional validity of friendships and relationships formed online. And in a particularly enlightening clip from a 2008 New York Public Library event, she speaks with close friend Toni Morrison about Morrison’s use of “we” in her writing versus Lebowitz’s use of “you”; her sarcasm about wanting to push away readers while Morrison aspired to embrace them has the legendary author choking on her water. (The docuseries is dedicated to the late Morrison.)

Scorsese pulls these interviews and conversations from years past and complements them with movie clips, musical performances, images of magazine covers and articles, and more intimate, present-day conversations between himself and Lebowitz to communicate the consistency of the latter’s reflective criticism, biting wit, and no-nonsense brusqueness. There is comfort in seeing how consistent she’s remained, and infectious excitement in watching the exuberance she pours into lengthy stories that jump from one detail to another. Lebowitz starts a story that begins with her memory of being a cab driver, then jumps to the Belmore Cafeteria (featured in Scorsese’s film Taxi Driver), where cab and bus drivers would get food at all hours of the night, then transitions to a discussion of why she became a driver rather than a waitress, then includes praise for how impressively waiters and waitresses in the city can recite the details of specials and menus, then muses about what dinner parties used to be like, before finally ending with “This is what it’s like to take a bus.”

This uninterrupted, stream of consciousness is about half of Lebowitz’s approach, while the other half is throwing out pithy observations one after another, waiting a split second to see what lands and what doesn’t, and then tweaking her one-liners as a result. Phones are too ubiquitous: “The only person looking where she’s going is me.” The subway is horrible: “New Yorkers have forgotten how to walk.” Apartments are too expensive: “I’ve joined my fellow Americans in being in psychotic debt for no reason at all.” Whether Lebowitz is sitting across from Scorsese at The Players club or standing in the middle of Robert Moses’ miniature Panorama Of The City Of New York in the Queens Museum, she’s always on.

Admittedly, Scorsese is an exceptionally warm audience for this, and he rarely asks Lebowitz any follow-ups or clarifying questions about her opinions. That prompting might have helped focus Lebowitz’s sometimes contradictory thoughts on the #MeToo movement, or her seemingly dismissive attitude toward inclusivity in art (“A book isn’t supposed to be a mirror. It’s supposed to be a door”). Such questioning might not have worked coming from Scorsese, who moves between a refreshing looseness with Lebowitz (when browsing genealogy books in the library in an attempt to find a record of his Italian family’s arrival in New York City, his dismissive “Norwegians, bah” is one of the series’ funniest moments) and a snappy return to directing after the two have been gabbing for a while (“Allora, andiomo, run it!” he instructs).

Perhaps teasing out Lebowitz’s opinions isn’t really what Pretend It’s A City is about; more accurately, this is a love letter to a certain version of New York City and to the film, art, and novels that helped shape Lebowitz’s and Scorsese’s generation. Pretend It’s A City is more of a confirmation and assurance of how viewers already think and what they already like than the gently challenging and curious nature of that other recent series about New York City, How To With John Wilson. Where Wilson was willing to wander around the city and find unexpected moments of strangeness and beauty in his endless filming, Lebowitz has her opinions already set in place, and you either agree with them or you don’t. She couldn’t care less. “Oh, Fran,” Scorsese says at one point, and that bemused vibe colors the entirety of the lovingly admiring, if slightly unchallenging, Pretend It’s A City.