Typewriters and Mug Shots: The Top 10 Literary Outlaws


It’s hard being a member of the creative class sometimes. Writers throughout history have been known to run afoul of the law, with charges ranging from disorderly conduct to murder. With the advent of the mug shot in the late 1800s, a latent image emerged of these various offenses, realized through this new, curious medium. In On Photography, Susan Sontag wrote, “The camera has the power to catch so-called normal people in such a way as to make them look abnormal.” But what if you’re unusual to begin with — what does the camera capture then? The following is a list of the top 10 authors to have walked the line.

1. Ezra Pound

In 1945, Pound was arrested by the US Armed Forces while living in Rome after he broadcast anti-American sentiments on Italian radio. The poet was taken to an army disciplinary training center near Pisa and eventually returned to the US, where he avoided a trial and was committed to a federal mental hospital in DC instead.

2. James Frey

The release of A Million Little Pieces in 2003 catapulted Frey to literary stardom. With Oprah’s seal of approval on the cover, the book sold ten million copies in two months. The fall was just as quick, however, with accusations of plagiarism catching up to the best-selling author on January 8, 2006, when The Smoking Gun ran an article denouncing Frey for embellishing — even outright fabricating — most of his criminal past. TSG writes, “The closest Frey has ever come to a jail cell was the few unshackled hours he once spent in a small Ohio police headquarters waiting for a buddy to post $733 cash bond.”

3. Kaye Gibbons

This North Carolina native was another Oprah favorite; in 1998, her book, Ellen Foster , was selected to be in Oprah’s Book Club. Ten years later, however, Gibbons was caught impersonating a physician in order to obtain an easy supply of painkillers, which she said she needed to complete her upcoming novel, The Secret Devotions of Mary Magdalene.

4. Dalton Trumbo

In 1947, the author of the anti-war novel Johnny Got His Gun was called to testify before the House Un-American Activities Committee. Trumbo refused to rat out his left-leaning friends in Hollywood, invoking the First Amendment. For his insubordination, he was found guilty of contempt and sentenced to ten months in prison, only to be blacklisted when he was released.

5. Isaac Babel

The NKVD arrested the venerable author of Red Cavalry in 1939 and falsely accused him of belonging to an anti-Soviet Trotskyite organization, as well as for spying for France and Austria. He was shot in Lubyanka prison in 1940, at the age of forty-six, becoming yet another victim of Stalin’s police state.

6. Malcolm X

Malcolm Little was sentenced to ten years in prison in 1946 on burglary charges. He began writing to Elijah Muhammad during this period, and his mentor advised him to give up petty crime. After serving six years, the former honors student was paroled, and eventually found his way to his pen pal on Chicago’s South Side.

7. Norman Mailer

After his arrest for stabbing his second wife, Adele Morales, with a pen knife in 1960, Norman Mailer told the judge, ”It is important to me not to be sent automatically to some mental institution, because for the rest of my life my work will be considered as the work of a man with a disordered mind. My pride is that as a sane man I can explore areas of experience that other men are afraid of.” Nevertheless, he was sent to Bellevue Hospital for a little over two weeks, after Adele decided not to press charges.

8. William S. Burroughs

What is it about brash male novelists and their second wives? Burroughs shot and killed his common-law wife, Joan Vollmer, in 1951 after a night of heavy drinking. The author attempted to shoot a highball glass off of Joan’s head…and missed. Read 97 Things You Didn’t Know About William S. Burroughs for more details.

9. Emma Goldman

This writer and rabble-rouser was arrested multiple times in New York and elsewhere in the early 1900s for making “incendiary statements” during her public speeches; for instance, “We will soon say to the Government: ‘Give us what belongs to us in peace, and if you don’t give it to us in peace we will take it by force.” Baby, you’re an anarchist!

10. Oscar Wilde

In 1894,the Marquis of Queensberry delivered his calling card to a porter at the Albemarle Club, a members-only bohemian writers’ haunt in London; it read: “To Oscar Wilde, posing as a somdomite [sic].” Incensed, Wilde approached a solicitor in order to press libel charges against the Marquis. When the case made it to court, Wilde realized he was the one on trial, and during his cross-examination he was repeatedly asked about the licentious subject matter in his novels. The author gamely replied, “There is no such thing as an immoral work; books are well-written, or badly written.”

Wilde never thought he would be tried at Old Bailey, but the verdict was decidedly “guilty,” and he served two years in prison.