For this special extended episode of About Art, Heidi Zuckerman sits down with Roberta Smith for an expansive conversation about looking, judgment, beauty, pleasure, criticism, marriage, retirement, and what it means to spend a lifetime paying attention to art. For more than 50 years, Roberta Smith has been one of the defining voices in American art criticism. She joined The New York Times in 1986 and became its first woman chief art critic before retiring in 2024. Her path began with the Whitney Independent Study Program, working with Donald Judd, and discovering a vocation that would place her in conversation with generations of artists and audiences. Roberta describes this conversation as her “exit interview,” and she and Heidi take their time. They discuss how to know what you think when you stand before a work of art, why looking requires rigor, and how encountering unfamiliar work can overturn even deeply held convictions. Roberta reflects on outsider art, Philip Guston, Lee Krasner and Jackson Pollock, the changing art world, and the responsibility of critics, curators, and dealers. They also explore the language of criticism, the power of writing for a public audience, the importance of passion in curating, and why beauty, taste, and pleasure deserve to be taken seriously. Roberta speaks candidly about gender, her marriage to fellow critic Jerry Saltz, the loss of a professional identity after retirement, and the possibility of finding a new relationship to the work she loves. At the heart of the conversation is Roberta's conviction that looking is an active, transformative experience—and that we must remain willing to be surprised, challenged, and changed by art. “Pleasure is its own form of knowledge.”