This essay will appear in somewhat different form in Fight of the Century, edited by Michael Chabon and Ayelet Waldman, to be published by Simon and Schuster in 2020 to coincide with the centennial anniversary of the American Civil Liberties Union.

It was a setup: a stratagem worthy of wily Ulysses himself.

The conspirators were Bennett Cerf, publisher and cofounder of Random House, and Morris Ernst, general counsel of the ACLU. The target was United States anti-obscenity law. The bait was a single copy of an English-language novel, printed in Dijon by Frenchmen who could not understand a word of it, bound in bright blue boards, and sold mail-order by the celebrated Paris bookshop Shakespeare and Company. When Cerf and Ernst first began to conspire in 1931, the novel, James Joyce’s Ulysses, was the most notorious book in the world.

“It is,” the editor of the London Sunday Express had written nine years earlier, sounding like H.P. Lovecraft describing Necronomicon:

the most infamously obscene book in ancient or modern literature….All the secret sewers of vice are canalized in its flood of unimaginable thoughts, images and pornographic words. And its unclean lunacies are larded with appalling and revolting blasphemies directed against the Christian religion and against the name of Christ—blasphemies hitherto associated with the most degraded orgies of Satanism and the Black Mass.

Regarded as a masterpiece by contemporary writers such as T.S. Eliot and Ernest Hemingway, celebrated for being as difficult to read as to obtain, Ulysses had been shocking the sensibilities of critics, censors, and readers from the moment it began to see print between 1918 and 1920, when four chapters were abortively serialized in the pages of a New York quarterly called The Little Review. Even sophisticated readers often found themselves recoiling in Lovecraftian dread from contact with its pages. “I can’t get over the feeling,” wrote Katherine Mansfield, “of wet linoleum and unemptied pails and far worse horrors in the house of [Joyce’s] mind.” Encyclopedic in its use of detail and allusion, orchestral in its multiplicity of voices and rhetorical strategies, virtuosic in its technique, Ulysses was a thoroughly modernist production, exhibiting—sometimes within a single chapter or a single paragraph—the vandalistic glee of Futurism, the decentered subjectivity of Cubism, the absurdist blasphemies and pranks of Dadaism, and Surrealism’s penchant for finding the mythic in the ordinary and the primitive in the low dives and nighttowns of the City.

It was not the book’s flamboyant modernism, however, that shocked and repulsed Mansfield and other early readers, among them Virginia Woolf, George Bernard Shaw, W.B. Yeats, and, of all people, D.H. Lawrence, who called its celebrated final chapter,…

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Copyright © 2019 by Michael Chabon