The title comes from the advice Lebowitz says she’d give people coming to New York City, a place she moved to from Morristown, New Jersey in 1969. Scorsese grew up in Manhattan, of course, and for much of the film, the two hold court in a few standard locations. The primary one is the Players, a Gramercy Park social club founded in the 19th century by actor (and brother of John Wilkes Booth) Edwin Booth. Another is inside the Queens Museum’s Panorama of the City of New York, the gigantic geographical model commissioned by Robert Moses for the 1964 World’s Fair. Wearing protective shoe coverings, Lebowitz towers over this massive representation of NYC like Gulliver in Lilliput. Offscreen, Scorsese asks questions while warning her to watch out for the bridges spanning the East River.
Editor Ellen Kuras mixes these one on ones with clips from audience Q&A’s, prior Lebowitz interviews with people like David Letterman and scenes of the humorist walking down the street. Occasionally, the film cuts to a still picture or a bit of historical footage of people like former NYC Mayor Abraham Beame, whose time in office coincided with the infamous NY Daily News headline “Ford to City: Drop Dead.” It’s during this time that Lebowitz plied her trade, writing pieces for Interview Magazine including a review of her co-star’s second feature film, 1972’s “Boxcar Bertha.” “I loved to write,” she tells Scorsese, “until the first time I had to write an assignment for money.”
Toni Morrison, to whom the series is dedicated, appears in interview footage as does Spike Lee, who grills Lebowitz on her dislike of sports. Seems she loves Muhammad Ali and was at Ali-Frazier I, a fight Lee reveres. Yet despite all this, she’s still a sports agnostic. Lee presses her on this, becoming animated as he goes on about Jordan and Lebron and Kobe. While he does, the film shows Lee at that memorable Knicks game where he heckled an unstoppable Reggie Miller from courtside. “You are the only person who argues with me more than my family,” Lebowitz tells Lee. Their spirited interplay is a highlight of the series.