In the glamorous world of New York City, Rebecca Bloomwood is a fun-loving girl who is really good at shopping – a little too good, perhaps. She dreams of working for her favorite fashion magazine, but can't quite get her foot in the door – until ironically, she snags a job as an advice columnist for a financial magazine published by the same company.

Three tales of love, ambition, and neurosis unfold in the city that never sleeps. In "Life Lessons" (Martin Scorsese), a tormented painter channels heartbreak into his art. In "Life Without Zoë" (Francis Ford Coppola), a precocious 12-year-old navigates privilege and loneliness in a Manhattan hotel. And in "Oedipus Wrecks" (Woody Allen), a man’s domineering mother literally becomes a looming presence over New York.

In August of 1949, Life Magazine ran a banner headline that begged the question: "Jackson Pollock: Is he the greatest living painter in the United States?" The film is a look back into the life of an extraordinary man, a man who has fittingly been called "an artist dedicated to concealment, a celebrity who nobody knew." As he struggled with self-doubt, engaging in a lonely tug-of-war between needing to express himself and wanting to shut the world out, Pollock began a downward spiral.

William Hundert is a passionate and principled Classics professor who finds his tightly-controlled world shaken and inexorably altered when a new student, Sedgewick Bell, walks into his classroom. What begins as a fierce battle of wills gives way to a close student-teacher relationship, but results in a life lesson for Hundert that will still haunt him a quarter of a century later.

After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a psychiatrist—she's a dreadful actress. David puts up with the leading man who is a compulsive eater, the grand dame who wants her part jazzed up, and Olive's interfering hitman/bodyguard—but, eventually he must decide whether art or life is more important.