For the past fifty years, Painting Group founders Aaron Shikler and David Levine have been meeting in New York City to create art and establish a sense of solidarity among the city's artists. Each week, the artists of the Painting Group come together to paint portraits. On this particular day, however, their subject is not just a random model but pioneering Supreme Court Justice Sandra Day O'Connor. As the artists begin painting their portraits, O'Connor shares anecdotes about the Supreme Court that are sometimes funny, but always fascinating. Shikler is no stranger to such famous subjects either; in addition to having painted a post mortem portrait for President John F. Kennedy for the White House, he has also painted portraits of First Ladies Jacqueline Kennedy and Nancy Reagan. Likewise, his talented partner Levine is well known for illustrations and caricatures that have appeared in The New York Review of Books among other publications. While some of the artists opt to paint a more traditional portrait of O'Connor, others take artistic license to create portraits that are a bit less conventional.