Anastasi moved to New York City in 1962 and promptly began making the work he is perhaps most well-known for and continues to create — his _Subway Drawings_, in which he blindly lets the movements of the subway car dictate the marks made on the page. These works are at the cornerstone of understanding Anastasi's approach to art making, as they are chance-driven, unbound to traditional aesthetic intent and depend solely upon the present moment. By 1970, Anastasi was actively showing in prominent galleries in New York, including solo shows, but was not finding the financial success of some of his contemporaries; he has always been considered, reverentially, as "an artist's artist." Following Kierkegaard's principle that "the love of repetition is in fact the only happy one," Anastasi continued to create works in this narrow, yet infinitely expansive mode, saying that "in repetition, things slow up. They get better, more beautiful, with the prospect of what is coming." This maxim of the rewards of repetition can be applied to Anastasi's body of work as a whole, as well as individual works, which deepen as you devote more time and attention to them. In the decades that followed, he continued to make subway drawings, as well as _Pocket Drawings,_ sound works, "unsighted" drawings, and site-specific works with a Duchamp-minded investigation into aesthetic prejudice and the presence of the artist in the work. Famously, Anastasi played a daily game of chess with his close friend John Cage for many years. Cage once said of Anastasi's work: "It's not psychological; it's physical." Anastasi was awarded the John Cage Award from the Foundation for Contemporary Arts in 2010 and is represented in major collections such as The Museum of Modern Art, New York, the National Gallery of Art, Washington D.C. and the Art Institute of Chicago. Referring to an adage often leveled at Duchamp – "either he's a genius or a crazy man" – Anastasi says its the "ambivalent feeling between the two that keeps \[him\] going as an artist...maybe it's insecurity or some sort of anxiety." Despite increasing and long-overdue scholarly and market interest in his work, Anastasi, citing yet another philosopher, identifies with Kant's declaration that "nearly through the whole of my work I have felt doubtful what to do." Anastasi continues to live and make work in New York.