Warning: the slideshow below contains images deemed obscene in the fifties.

Fifty-seven years ago today, the Supreme Court rendered its decision in Roth v. United States, the preeminent obscenity case of the time. That Roth isn’t Philip—not that he’s any slouch when it comes to indecency—but Samuel, a widely reviled publisher perhaps most remembered today for bootlegging portions of Ulysses. As Michael Bronsky described him in a piece for the Boston Phoenix,

Roth became so notorious as both literary pirate and smuthound (the word in use at the time) that he was attacked in The Nation and The New Yorker as a literary fake and social nuisance. Vanity Fair included him, along with the up-and-coming Adolf Hitler, in its 1932 photo essay titled “We Nominate for Oblivion.”

In the course of his long and thoroughly ribald career, Roth often found himself dragged to court—this particular case saw him violating a federal statute that banned the transmission of “obscene, lewd, lascivious, or filthy” materials using the postal service. Roth had been doing just that: his magazine American Aphrodite (“A Quarterly for the Fancy-Free,” the covers of later editions said) was the finest in literary smut. (And trust us: The Paris Review knows a thing or two about literary smut.)

Impressively—and perhaps profligately—American Aphrodite was a clothbound publication; take a look at the covers above to get a sense of its tenor. The titles of the work Roth published are by turns gently titillating (“The Willing Maid a Day Too Young,” “A Lover Without Knowing It,” “Take It Off! Take It Off!”), ridiculously frank (“Gallery of Big Women in the Nude,” “Japanese Ladies Taking Their Bath”), or simply bizarre (“The Two-Thousand Pound Raspberry,” “Shake Your Goat-Leg,” and a four-part series called “The Women of Plentipunda”). Bronsky writes,

American Aphrodite usually featured things like mild erotic line drawings, some piece of long-out-of-print British literature (the “scandalous” seventeenth-century plays of Aphra Behn appear in many issues), a “bawdy” new translation from Chaucer, and something truly shocking, like nude photos of ten-year-old girls taken in Victorian brothels.

And in his 2013 book, Without Copyrights: Piracy, Publishing, and the Public Domain, Robert Spoo explains that the magazine

contained a typical Rothian stew of slightly dated literature and winking erotica, though some of the material, such as Aubrey Beardsley’s unfinished novel Venus and Tannhäuser, contained stronger sexual content. Woodcuts and drawings of thinly clad or nude women adorned the quarterly’s pages, along with frank poems, such as one inquiring of God whether it is wrong to desire “Two women in one affection, / Two vulvas, four breasts” … Roth’s editorials chided “Madame Post Office” and other official powers for repressing “our rights as American citizens engaged in interpreting the cultural and emotional motives of our time.”

For better or worse, that repression continued with Roth v. United States, in which a six-person majority submitted that obscene material wasn’t protected by the First Amendment, and that said material could be defined as that whose “dominant theme taken as a whole appeals to the prurient interest [to the] average person, applying contemporary community standards.” The court maintained that Congress could ban any material fitting this definition; it upheld Roth’s conviction, and he went to prison. The verdict held until 1973, when it was superseded by Miller v. California, which also involved sending smut through the mail—another story for another day.