How is it that between 1922 and 1934, James Joyce's Ulysses, considered the greatest English language novel of the twentieth century, could not get published in the United States without risk of prosecution and jail? How did American law get its ideas about obscenity and censorship so wrong? This Article closely analyzes the facts and the reasoning,or lack of reasoning,in R. v. Hicklin, the Queen's Bench decision of 1868 whose throwaway single sentence defining obscenity was reflexively adopted by American courts and became the greatest legal impediment to artistic freedom in the United States for nearly a century. The Article traces Hicklin's influence in the United States through the first third of the twentieth century. Using archival and other sources, it then closely examines the first court test of a part of Ulysses,in New York in 1920-21, a case that might have been won, but ended in the obscenity convictions of two women who published an obscure literary magazine. Their convictions impeded publication of the book until Morris Ernst's brilliant legal strategy gave his client, Random House, confidence that it could publish Ulysses in the United States without fear of prosecution. While the district court decision in Ernst's favor is rightly applauded for freeing Ulysses, the judge's reasoning does not resemble anything we can recognize as law. It is a decision for one book only. Even Augustus Hand's opinion for the Second Circuit affirming Ernst's victory, which cousin Learned joined and which contains the seeds of modern obscenity doctrine, required some jurisprudential sleight of hand to escape unfavorable circuit and Supreme Court precedent. The story from Hicklin to Ulysses II is both riveting in itself and as legal and cultural history. But it is also a lesson about harm done when government interferes with the intellectual and personal autonomy of individuals.