Oscar Wilde took on the challenge of teaching us how to live artfully. From the dynamic successes and tragedies of his own life Oscar knew that everything worthy of existence is worthy of art, including its ugliness and suffering. Oscar observed much about human nature, especially his own, in an era when convention was not challenged, knowledge was taught and appearances were everything. For him, “The supreme vice is shallowness.”1 Society and psychoanalysis can still be honored and shaken by his words. The paradoxical and complex nature of Oscar's insights was as good as any coming from a thoughtful psychoanalyst. After the first two attempts to write about Oscar fell flat, it became clear that I must engage with him and try to match the unsparing commitment to explore his unconscious and interior life. In the process of creating the array of sketches of my psychoanalytic encounters with Oscar, I also found the words to describe what drew me to the field some 20 years ago—the art of psychoanalysis.