Authors Behind Bars

This list of literary jailbirds may surprise you.

Authors Behind Bars

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If you think of all authors as bookish, bespectacled professorial types, think again. Turns out quite a few literary legends have spent some time in the slammer.

And it wasn’t for unpaid speeding tickets. Folks like Dorothy Day, Chester Himes, and Nelson Algren were cuffed for crimes that include picketing the White House, armed robbery, and the good old-fashioned five-finger discount.

And those are just the ones who got caught. William S. Burroughs shot his wife and evaded Mexican authorities, Allen Ginsberg pled insanity on a drug charge and went to a mental hospital, and we have it on good authority that John Green jaywalked once.

Here’s the lineup.


Oscar Wilde

Wilde was jailed for “gross indecency” after admitting to being homosexual. Just another dick move by the British government. (Don’t even get me started on the Boer War.) At least he got to write De Profundis during his incarceration.


Chester Himes

The literary and mystery author Chester Himes had a rough go of it. He played a prank in college, got kicked out, resorted to armed robbery, and got caught. But he used his time in the brig to embark on his literary career, eventually winning multiple awards and the literary sponsorship of Langston Hughes.


Miguel de Cervantes

Before he wrote Don Quixote, Miguel de Cervantes was a tax collector. And apparently not a very good one. He got sent to the big house for irregularities in his accounting.


Howard Fast

Spartacus and April Morning author Howard Fast had the deep misfortune of being a socialist and experimenting with communism during the McCarthy era. After refusing to rat out his buddies before the notorious House Un-American Activities committee, Fast got three months in prison for “contempt of congress.”


Fyodor Dostoyevsky

Russian Author Fyodor Dostoyevksy was also burned for his political beliefs. He and his literary group were liberal Utopians, which led to them being rounded up by the Tsar and sentenced to execution by firing squad. His sentence was commuted at the last second to 10 years hard labour in Siberia. Crime and Punishment indeed.


Jack London

In his youth, the author of The Call of the Wild was arrested for vagrancy—an old term for homelessness—and sentenced to 30 days in a Pennsylvania penitentiary. Only after other misadventures, scurvy, and a time hunting gold in the Klondike did London finally find literary success.


Joan Henry

Joan Henry, novelist, playwright, and screenwriter extraordinaire, passed a fraudulent check given to her by a friend. Eight months in jail later and she had transformed from a romance writer to a writer of serious literary fiction and memoir with The Weak and the Wicked, based on her experiences in prison.


Daniel Defoe

The author of Robinson Crusoe got his start writing fiery pamphlets in support of social justice, King William III, and free protestantism. When the Anglican Queen Anne took over, Defoe got stuck in a pillory (the thing where the police put you in a wooden headlock and encourage people to throw vegetables at you) and then jail, which is pretty rotten luck.


O. Henry

William Sydney Porter, better known by his pen name and eponymous literary prize O. Henry, was either a terrible clerk or embezzled from his Austin bank employer. Either way, he was sentenced to five years at the Ohio penitentiary, where he began writing under the famed pseudonym. After getting off early for good behavior, O. Henry went on to write more than 380 stories.


Nelson Algren

Algren didn’t begin his writing career auspiciously; he was caught stealing a typewriter and spent three months in prison. Thankfully, he got released early so he could win an O. Henry award and write the classic The Man with the Golden Arm.


Dorothy Day

Day was a Catholic social activist as well as an author, spent 30 days in jail for picketing the White House. With multiple biographical films and a nomination for sainthood under her belt, we think it’s best not to hold her criminal record against her.


Henry David Thoreau

Thoreau was so disturbed at the idea of paying taxes to fund the Spanish American War—which he considered immoral—that he stopped paying them altogether. He was arrested and put in jail until a relative paid for him against his will. The experience led to the tract Civil Disobedience, which inspired Ghandi and Martin Luther King Jr. in their work of nonviolent protest.


John Cleland

Back when the British were still imprisoning people for terrible reasons, Cleland was sent to debtors prison for over a year. While in prison, he wrote the infamous novel Fanny Hill: Memoirs of a Woman of Pleasure. Six months after his release, he was arrested again for writing such a shocking novel (“woman of pleasure” is a fancy way of saying prostitute). Perhaps due to his previous experience, Cleland immediately renounced the book.


Seth Morgan

Morgan became addicted to heroin and resorted to robbery to support his habit. He got caught, but used his time in prison and time as an addict as inspiration for the novel Homeboy. Though he continued to battle addiction, he retired from criminal pursuits.


Bertrand Russell

The British philosopher and author managed to be jailed several times, including once 87 years old for attending an anti-nuclear protest. Far from being afraid of jail, Russell at times sought it out, hoping to raise awareness for his pacifist beliefs.


Sir Walter Raleigh

Raleigh, ever the Elizabethan jack of all trades, was a poet, writer, noble, and spy. But he also married one of Queen Elizabeth I’s ladies in waiting without her permission. When the secret marriage was discovered they were both packed off to the tower of London. The damage wasn’t too bad however, as he went on to become an explorer and member of parliament—before being executed at 65 by King James for no good reason.


Ken Kesey

Kesey was so desperate to get out of jail time for his marijuana charge that he faked his suicide and fled to Mexico for eight months. But the One Flew over the Cuckoo’s Nest scribe and Oregon native eventually came back to the the states to serve his five-month sentence. If he’d only waited 50 years, marijuana would have been legal.


Edward Bunker

Edward Bunker fell early into a life of bank robbery, drug dealing, extortion, armed robbery, and forgery. After 18 years in and out of prison, Bunker finally found a more lucrative pursuit: writing. He went on to write several books and appear in multiple movies, publishing a semi-autobiographical novel of a boy’s descent into crime Little Boy Blue.



This sassy playwright and advocate for free speech once got thrown in the Bastille for 11 months for writing a harsh satirical poem on the French nobility. Who knew poetry was so dangerous?



Harlan Ellison

Though the notoriously cantankerous Hugo and Nebula award-winning writer/editor Harlan Ellison didn’t go to prison, he did spend a night in jail after a nosy neighbor called the cops about his weapons collection. He was so fired up about the incident that wrote an article about it in the Village Voice.

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