In Black and White: 10 Famed Literary Jailbirds

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The internet has been hopping this past week with the news that Lil’ Wayne is set to release Gone Till November, a memoir based on the journals he kept during his eight month stint at Rikers Island, this fall. Weezy’s transformation to memoirist got us to thinking about other famous literary jailbirds — whether they wrote in jail, wrote after coming out of jail, or were imprisoned for their writing. As you might imagine, going to prison seems to be almost a rite of passage for a canonical author — at least it used to be — so it looks like Weezy is heading down the right path. Click through to read our list of ten famed literary jailbirds.

The Marquis de Sade

The libertine of all libertines spent about 32 years in prisons and one insane asylum during his life, including ten years at the Bastille, and wrote most of his novels behind bars — possibly in large part to pass the boring, lady-less time. He was arrested several times for acts of blasphemy, indecency and alleged abuse, and only was able to publish any of his writing in his relatively brief periods of freedom. Even so, in 1801, when Napoleon Bonaparte himself called for the arrest of the anonymous author of Justine and Juliette, Sade was thrown back in jail right away, before being declared legally insane in 1803 and moved to the asylum at his family’s petition.

Jean Genet

After being dishonorably discharged from the French foreign legion, Genet returned to Paris where he was in and out of jail for theft, lewd acts, use of false papers, and vagrancy. It was in prison that he secretly wrote his very first poem, “Le condamné à mort,” and his largely autobiographical first novel, Our Lady of the Flowers. Soon after, he sought out Jean Cocteau (or for the days when these kinds of people were just milling about, waiting to be approached!) and showed him his writing — with Cocteau’s help, Our Lady of the Flowers was published. In 1949, after ten convictions, Genet was threatened with a life sentence, but Cocteau, as well as Genet’s new friends, Jean-Paul Sartre and Pablo Picasso, successfully petitioned the French President to save him. He would never be imprisoned again.

O. Henry

While working for the First National Bank of Austin, famed short story writer O. Henry (William Sidney Porter) was arrested on charges of embezzlement and eventually jailed. Because he was a licensed pharmacist, he had a relatively easy time of it — he had his own room in the hospital wing and worked as the night druggist. More importantly, he published fourteen stories while in prison, having a friend forward them from New Orleans so no one would know their author was a jailbird, and it was during this time that the pseudonym “O. Henry” began to stick.

e.e. cummings

While Cummings served in the French ambulance corps in WWI, he and a friend began writing letters home about the inefficiency and ineffectiveness of the healthcare system they were working in. The French authorities, incensed by some antiwar sentiments expressed in the letters, threw the pair in jail, a turn of events Cummings thought rather ironic, seeing as he was actively aiding the French war effort. No matter, though — he turned the experience into his first literary success, the 1922 autobiographical novel The Enormous Room.

Jack London

Before he became the writer we remember today, Jack London worked a series of odd jobs — everything from factory worker to oyster pirate — before joining up with a group of unemployed west coast drifters who called themselves “Kelly’s Army” and meant to march on the capital. That plan never materialized, but London did end up making it to New York City, where he was arrested and spent thirty days in jail on charges of vagrancy. Don’t worry — he made it home again and finished high school.

Henry David Thoreau

Though we admit that Thoreau’s short stint in the clink doesn’t exactly make him a jailbird, we still think it bears mentioning, at least for symbolic reasons. During his two-year period living at Walden Pond, Thoreau spent a single night in his local jail when he refused to pay his poll tax, a decision he made to protest the US’s war with Mexico. According to legend, Ralph Waldo Emerson visited him that night and asked him, “Why are you here?” Thoreau replied, “Why are you not here?” The night would serve as inspiration for an essay called “Resistance to Civil Government” — though the name was ultimately changed to “Civil Disobedience.”

Miguel de Cervantes

In his prologue to Don Quixote, Cervantes describes the novel as having been “begotten in a prison.” Indeed, the author found himself in debtor’s prison two or three times in his life, and so would have had ample time to think on his literary masterpiece. He clearly did not spend any of that time thinking up money-making schemes.

Oscar Wilde

At the height of Wilde’s success — post-Dorian Gray and while his masterpiece The Importance of Being Earnest was still showing in London — he rather unwisely levied charges against the Marquess of Queensberry, the father of his lover, Lord Alfred Douglas, for libel. During the trial, the Marquess proved that his accusations of sodomy (which was illegal at the time) were true, and Wilde was himself arrested and convicted of “gross indecency” with other men and spent two years serving hard time, during which he wrote the regretful De Profundis.

Fyodor Dostoevsky

Dostoyevsky was incarcerated near the beginning of his writing career, at age 27, for his membership in the liberal intellectual group the Petrashevsky Circle. He was sentenced to four years of exile and hard labor at a prison camp in Siberia, and after those years were completed, was required to serve in the Siberian Regiment. His time in jail very much changed both his outlook and his writing style — he began to strongly argue against the Nihilist and Socialist viewpoints, instead championing humility and suffering, and his writing became darker and more complex, abandoning the character-based lighthearted works he had been experimenting with.

Malcolm X

Like Dostoevsky, Malcolm X’s years in prison had a formative effect on his life. In 1946 he was charged with larceny and breaking and entering and he was sentenced to eight to ten years in prison. He met John Elton Bembry, a self educated man whom he later described as “the first man I had ever seen command total respect … with words.” Under Bembry’s tutelage, Malcolm X began to educate himself, becoming a voracious reader. Then, his family wrote to him encouraging him to join the Nation of Islam, which he eventually did, and before he left prison had dubbed himself ‘Malcolm X.’