Author Jack Black and his one book.


Jack Black was a burglar, rambler, jailbird and writer whose lone published memoir, You Can’t Win (1926), was an important early influence on William S. Burroughs and, through him, the other Beat writers. With a film adaptation of the book, starring Michael Pitt, expected later this year, now is a good time to rediscover this classic road narrative. Anthony Mostrom tells the story of Jack Black through his own words and those of Burroughs.

 “I first read You Can’t Win in 1926, in an edition bound in red cardboard,” William S. Burroughs writes in the introduction to a paperback reissue of Jack Black’s classic story. Burroughs never made a secret of the profound influence upon his youthful mind, back in suburban mid-1920s St. Louis, of one book above all others, the true confessions of a wandering West Coast safecracker, petty thief and hobo from the pre-WWI era named John “Jack” Black.

 “At last the night came that I had decided was to be my last in the town,” Black wrote in his book. “I had done everything possible in the way of precaution and protection. The stormy night favored me and the box gave up its contents after a few sturdy blows from a short-handled sledgehammer… The train arrived on time, and when it pulled out I got aboard without a ticket. That was part of my plan…”

 You Can’t Win opens with its author describing his own alienating, off-putting, asymmetrical face, which never opened any doors for him: “I do not scowl, I do not sneer, yet there is something in my face that causes a man or woman to hesitate before asking to be directed to…church. I can’t remember a time that any woman, young or old, ever stopped me on the street and asked… Once in a great while a drunk will roll over to where I am standing and ask how he can get to ‘Tw’ninth n’ Mission.”

 “Before my 20th birthday,” he wrote, “I was in the dock of a criminal court, on trial for burglary…I had become a snapper-up of small things, a tapper of tills, a sneak thief, a prowler of cheap lodging houses, and at last a promising burglar in a small way. At 30 I was a respected member of the ‘yegg’ (safecracker) brotherhood…silent, secretive, wary…forever traveling, always a night worker…”

As Black concludes here: “A bleak background!”

Jack Black

It’s well known among seasoned fans of Beat literature that Black’s account of his days as a footloose, “rail-rodding” criminal up and down the coast of both the USA and Canada struck a major chord in the bookish, 12-year-old Burroughs’ mind, one that was already excited by guns (young Burroughs loved hunting with his dad), travel, and of course gangsters…the Chicago of Al Capone being not that far away from St. Louis.

What Burroughs especially took to heart was the author’s description of the “Johnson family,” a sort of idealized brotherhood within the old-time American underworld, whose ‘code’ Burroughs liked to recite often, many years after reading Black’s book: “A Johnson pays his debts and keeps his word,” Burroughs recalled, from what he always referred to as ‘the good red book.’

“He minds his own business, but will give help when help is needed and asked for. He does not hold out on his confederates.” This last point no doubt resonated in Burroughs’ mind later in life, when he toyed with petty crime in wartime New York City, dealing heroin and morphine with the likes of his then-confederate, a Times Square street hustler and thief named Herbert Huncke.

Already as a boy, Burroughs found the salty, all-male world that rose up from the pages of Jack Black’s book, with its implied deadly rivalry between what Burroughs liked to call “the Johnsons vs. the Shits” (a word you’ll notice that’s very close to “snitch”) appealing to his precocious sense of American nostalgia and ragged righteousness tinged with criminality.

“The old hop-smoking, rod-riding underworld had a name for it: a member of the Johnson Family,” Burroughs wrote, in an essay called My Own Business. “They are found in all walks of life: the cop who slipped me a joint in a New Orleans jail, for instance. Or when I was pushing junk in New York back in 1948, the hotel clerk who stopped me in the lobby: ‘I don’t know how to tell you this, but there is something wrong about the people who come to your room, so I just wanted to warn you…be careful and tell those people to watch what they say over the phone’…”

“Yes,” Burroughs went on, “this world would be a pretty easy and pleasant place to live in if everybody could just mind his own business…but as a wise old black faggot said to me years ago, ‘some people are shits, darling.’ I was never able to forget it.”

Recalling a favorite passage from You Can’t Win in the Introduction he wrote for a 1988 reprint of the book, Burroughs relished certain gory details:

“This young gay cat starts badmouthing Salt Chunk Mary…and old George, a rail-riding safecracker with two fingers missing from crimping blasting caps, says to him: ‘You were a good bum, but you’re dog meat now,’ and shot him four times across the fire at a hobo jungle, and I could feel the slugs hit him. He fell down with his hair in the fire.”

Young Bill Burroughs was already gay and alienated, already fooling around with drugs and other mind-altering potions; he was countercultural avant le lettre. His eventual dislike of modern settled America, which he once described as “not so much a nightmare as a non-dream,” a place where the only choice was to become a deviant or die of boredom (and we know which way that went for Burroughs) would later crystallize into full-blown paranoia, for example when he condemned women, as a species, who were no doubt plotting to smother all men under a blanket of matriarchy, as the “sex enemy.” Yes, William Burroughs the pre-WWII homosexual and gun-loving, smack-injecting pornographer, was a bit of a misanthrope.

Burroughs seemed always to be fighting against his privileged background as if it were a suit that didn’t fit, while “scanning the horizons for new frontiers of depravity” for art’s sake, whereas Black started out on the low road and sunk even lower.

Jack Black meanwhile, as revealed in You Can’t Win, was clearly an unusual personality himself. Aside from being a master survivalist (albeit a beaten-down one), he was bright and well-read (it’s said that he read the entire Encyclopedia Britannica during one of his longer stretches in prison) as well as crafty, self-aware, magnanimous, and from beginning to end, incorrigibly dishonest…though candid about that in a joking kind of a way, which is something you often find in the memoirs of intelligent criminals.

Reading certain passages of You Can’t Win can give you an instant taste of the windswept, far northwest exoticness of Black’s early-century adventures in crime and close-call escapes: usually by train, either by railroad compartment (that is to say, civilian style) or by boxcar (that is to say, “riding the rods” hobo style). The book is filled with strange bits of information that a suburban boy in the Midwest like Billy Burroughs could never have learned anywhere else:

“Harvest workers were called blanket stiffs or gay cats, and the process of pistoling them away from their money was known as catting them up. Bands of yeggs worked with the brakemen, who let them who let them into the cars, where they stuck up the cats, took their money, and forced them to jump out the side doors between stations.

 “When Spring came, my Chinese ‘tillicum,’ which is Chinook for friend, and I were the only felony prisoners in the ‘skookum house,’ or jail. At the provincial jail I found a drunken Scotchman in charge. He was assisted by two half-breed Indian boys serving six months each. Both of them watched me faithfully and fed me regularly when the jailer was drunk. There was not a fixture in the cell but a bucket. I had plenty of blankets and slept on the floor. Not a smoke, nor a paper, book nor magazine was allowed in the jail. When I asked the Scotchman for something to read, he got me a Bible which I read…with much interest but no profit.

 “All day, every day, I read my Bible and prayed that the conductor might fall under his train before the day of my trial.”

 There were of course extreme similarities and contrasts between Jack Black (1871-1932) and William Burroughs (1914-1997), in their lives and their writing. Both were left unmoved by traditional religion. Burroughs seemed always to be fighting against his privileged background as if it were a suit that didn’t fit, while “scanning the horizons for new frontiers of depravity” for art’s sake, whereas Black started out on the low road and sunk even lower. The only way Jack Black knew how to get by, until he began writing later in life, was stealing. As an incorrigible with no education worth the name, he couldn’t help himself. Both harbored secret literary ambitions well into middle age before acting on them.

Both were hopheads (smokers of opium). Burroughs wrote obsessively about sex, but even if Jack Black wanted to, that wouldn’t fly in the 1920s: he originally wrote the book as a series of newspaper articles anyway. Burroughs was able to live comfortably (though always, shall we say, low-grade comfortably) on many continents, thanks to the generous allowance his parents mailed to him year after year, as he traveled from Morocco to Paris to London to New York to…Lawrence, Kansas. Jack Black in the end wasn’t making it once the first flush of success faded, and he drowned himself in the East River during the lowest depths of the Depression, in 1932.

You Can’t Win was championed by such major literary figures as H.L. Mencken and the poet Carl Sandburg, which helped to make Black’s book a bestseller when it was published in 1926. Mencken’s highbrow magazine The American Mercury, which championed the writings of Nietzsche, Theodore Dreiser and historian Oswald Spengler, also praised Jack Black, the con who never went to school: “Not since the days of Jack London has such a story come out of the bold, bad Frisco of the early part of the century.” Clarence Darrow, the famous attorney who saved child killers Leopold and Loeb from the death penalty, called You Can’t Win “fascinating from beginning to end…Jack Black has written a remarkable book.”

What young William Burroughs didn’t know, but Jack Black surely did know, was that Mencken and other high-profile literary lions, such as Jack London himself (an early hobo writer) had already promoted a number of Californian convict authors, elevating them to the forefront of the American literary scene of the 1920s. Beyond making careers, some of these books had a real impact on society, resulting in the so-called Prison Reform movement of that era.

“Not since the days of Jack London has such a story come out of the bold, bad Frisco of the early part of the century.”

Probably the most influential of all of these “con authors” was a mysterious figure named Ed Morrell, who wrote a book in 1924 called The 25th Man, a book whose searing descriptions of the incredibly hellish tortures he went through in the dungeons of Folsom and San Quentin, punishments meted out with a bullwhip and other, more sinister devices for even minor infractions, resulted in a public uproar to abolish torture in American prisons. Jack London even used Morrell’s example of survival under such extreme conditions as the inspiration for his novel, The Star Rover. But Morrell’s own book was much grittier. From a chapter titled Torture, A Fine Art at Folsom:

 “’Good God,’ I thought. ‘Fifty hours hanging by the wrists in the derrick!’ The torture chambers in Folsom were located in what was called the ‘back alley.’ My arms were extended backward and then a pair of handcuffs were snapped upon my wrists. One of the convicts began pulling the rope which was attached to the handcuffs, drawing me slowly upward…but he was brushed aside by the dungeon warder who grasped it…and with the full weight of his body gave it a savage jerk.

 “The weight of my body caused the steel of the handcuffs to cut deeply into my wrists, as I swung limply at the end of the block and tackle. My head was tilted downward to the level of my waist…my first sensation was one of reeling drunkenness, caused by the blood rushing to my head…

 “There was a cold splash of water. It revived me, and I half-consciously made out the form of one of the convicts playing a hose upon me. I had been hanging two hours and ten minutes…”   

Ed Morrell in San Quentin State Prison, 1896.

 Americans on the “outside” in those days were genuinely shocked to learn that such conditions prevailed in their country’s prisons, though it’s actually pretty easy to believe such things were going on back in those bad old days of lynchings, the resurgent Klan, harsh physical punishment meted out as a matter of routine in insane asylums and even school classrooms, and other casual cruelties of that era.

There was, of course, a prurient and sensationalistic appeal to these books. Morrell’s book came out just two years before You Can’t Win, and it could be said that Jack Black benefited from the sufferings of his ex-con elder: by the time his book came out, the American public had developed a definite taste for juicy prison memoirs, the more gory and grotesque the better. Twelve-year-old Billy Burroughs was one of them.

(In a strange pop-cultural twist, Jack Black would record in his book the severe beating he’d once endured in Western Canada, carried out by a prison guard named Burr; crime historians have since determined that this man turns out to have been the grandfather of Perry Mason actor Raymond Burr.)

Meanwhile, it’s a safe bet that William Burroughs, who would one day spend time inside a Mexican jail for killing his wife, probably never had a chance to read Morrell’s The 25th Man, a book that could scare anyone off from even the remotest possibility of being incarcerated. But young Billy sure would have enjoyed it.

Billy Burroughs on left, with his brother Mort and their father, ca. 1922.

“As a young child, I wanted to be a writer…I thought that they led very glamorous lives, living in Tangiers and smoking hashish and sniffing cocaine in Mayfair…”

As an adult, Burroughs shot his wife through the head while drunkenly trying to repeat a long-practiced “William Tell” act which they’d both indulged in many times before, on their clandestine marijuana farm in Texas just following WWII (see Rob Johnson’s book the Lost Years of William S. Burroughs, Beats in South Texas: walking through the fields, Joan Vollmer Burroughs would put a grapefruit on top of her head, and Bill would shoot at it). It was at a drunken party in an apartment above a bar in Mexico City, in September of 1951, when Burroughs drawled, “well it’s about time for our William Tell act,” and pulled a handgun out of a traveling bag. Joan put a cocktail glass on top of her head and giggled.

Following a decade of heroin addiction and wandering around the world, William Burroughs, the childhood imbiber of Jack Black and experimental writers like Celine and Andre Gide, grew up to write passages such as this in his classic hallucinatory novel composed of disconnected prose fragments, Naked Lunch:

 “I can feel the heat closing in, feel them out there making their moves, setting up their devil dolls stool pigeons, crooning over my spoon and dropper I throw away at Washington Square Station, vault a turnstile and two flights down the iron stairs, catch an uptown A train… 

 “Look down at my filthy trousers, haven’t been changed in months…the days glide by strung on a syringe with a long thread of blood… Dead fish eyes flicker over a ravaged vein…

 “Time jump like a broken typewriter, the boys are old men, young hips quivering and twitching in boy-spasms go slack and flabby, draped over an outhouse seat, a park bench, a stone wall in Spanish sunlight, a sagging furnished room bed…

 “The Old Man will rush out of a little black hut cursing, with a pitchfork and the boy run laughing across the Missouri field – He find a beautiful pink arrowhead and snatch it up as he runs with a flowing swoop of young bone and muscle (his bones blend into the fields, he lies dead by the wooden fence a shotgun by his side…) The catfish billows out behind him…he come to the fence and throw the catfish over into blood-streaked grass…the fish lies squirming and squawking – vaults the fence.

 “…the Old Man scream curses after him…his teeth fly from his mouth and whistle over the boy’s head, he strain forward, his neck-cords tight as steel hoops, black blood spurt in one solid piece over the fence and he fall a fleshless mummy by the fever grass. Thorns grow through his ribs, the windows break in his hut, dusty glass-slivers in black putty, rats run over the floor…”

 Naked Lunch was published in 1959 (originally as The Naked Lunch). This was before his novels Nova Express and The Ticket That Exploded, both composed partially through use of Burroughs’ “cut-up” technique of scissored chunks of writing which he took from any number of sources: newspapers, novels, poetry, his own writings etc., all recombined to “cut / shift / tangle word lines,” Burroughs’ own version of the nineteenth-century poet Arthur Rimbaud’s goal of attaining “a systematic derangement of the senses” through writing. Rimbaud, Burroughs and Jack Black all smoked opium.

Some otherwise ultra-hip writers of the late 1950s, like the British novelist and philosopher Colin Wilson, were revolted by Naked Lunch: “To speak of murder is by no means irrelevant in the context of Burroughs. Sadistic sexual killers often lay out the victim’s body in a display that is designed to create shock. The Naked Lunch is as close as it is possible to come, on the page, to displaying a mutilated corpse.” But other writers like Norman Mailer, sci-fi author J.G. Ballard and even Time magazine were lavish in their praise for this “booty brought back from a nightmare.” Stanley Kubrick went on record as a fervent Burroughs admirer.

Perhaps inevitably, Jack Black the western “highwayman” would end up serving time in both San Quentin State Prison and Folsom State Prison.

Jack Black in Folsom State Prison, 1898.

Here for comparison is an old, generally accepted description of the two: quoting one historian, “the history of San Quentin has its diverting moments, but the history of Folsom is a record of almost unrelieved grimness.” Documents housed at the California State Archives reveal that a young Jack Black was serving time for “assault to commit murder” in 1904 and somehow gained an early release in 1906 (shortly after the San Francisco earthquake and fire), thanks to some solicited and highly fanciful testimonials from his friends, written to the Governor. These bits of malarkey praised the young man as a fine, upstanding citizen, “always gainfully employed…”

An April 18, 1904 newspaper story from the San Francisco Call, however, tells a different story:

 “The suspicion entertained by Detectives Bunner and Freel that Jack Black, alias Tom Callahan, ex-convict, was implicated in the recent string of holdups in the Mission was verified yesterday. Black was arrested on Eddy Street last Friday night, after a desperate fight with the capturing officers.

 “Yesterday afternoon Frank Campbell, a teamster…identified Black as one of the two men he saw who had a running revolver fight with Policemen Skelley and Walsh on the night of April 10 in the neighborhood of Twenty-Third and Dolores Streets…

 “When Black reached San Jose Avenue he wheeled and said to Campbell, ‘If you don’t quit following me I’ll shoot you.” Then he ran along San Jose Avenue to Twenty-Third Street, Campbell still in pursuit. Black…jumped upon a passing car…  

 “Another fact that confirms the suspicions against Black is the finding of a cartridge on Fair Oaks Street. Black, during his flight, ran along Fair Oaks Street, and it is believed that he dropped the cartridge while reloading his revolver. The cartridge bears the name ‘Peters’ and those found on Black when arrested bear the same name. The officers say they have never known of any cartridges of that brand.”


After a life of constant danger and decades spent in and out of prisons and jails, Jack Black’s life changed in a way that very few prisoners could ever dream of, becoming the best-selling author of a book about his crimes. This happened thanks to his champion and advocate: a long-forgotten ‘bigwig’ of old San Francisco named Fremont Older, the liberal editor of the old San Francisco Call newspaper.

Fremont Older-1919

Older had made a habit of championing some of the City’s most hopelessly lost criminals: murderers, bank robbers, back alley abortionists and pimps, urging them to write up their stories for his paper, which was part of the Hearst chain. He called these stories “the Voice from the Underworld.” Older himself was accused of being a “sentimentalist,” which in those days meant a soft-hearted liberal. He did write many a corny editorial about his belief in “the goodness of man” and that kind of stuff, but he put his beliefs into practice by supporting and encouraging hard cases like Jack-the-burglar. In Black’s case, what Older did was talk to the judge who had just committed Black to a very long ‘jolt’ in San Quentin of 25 years, and had it reduced to one year. Black was ecstatic: “One year! I can do that standing on my head!”


You Can’t Win opens with the words, “I am now librarian of the San Francisco Call…” Older had given him that job. “The course I followed from convent school to this library desk, if charted on a piece of paper, would look like (a) zigzag line…every turn I made was a sharp one, a sudden one. In years I cannot remember making one easy, graceful, rounded turn.”

Fremont Older knew he hit the jackpot when he discovered Jack Black: here was a rare find, a hardened and battered criminal with a long string of fuck-ups who had literary talent and managed to keep his sense of humor intact. Black spent many pleasant summers with Older and his wife at their rustic ranch (known as “the Gulch”) outside San Francisco. He was handyman and a kind of wise old sage there, always treated by them as an honored guest. Eventually, the Gulch became a refuge for other pardoned ex-cons.

Jack Black

The Olders apparently were in awe of Black: his wisdom and his wit. “He is in a class by himself,” Older wrote in his memoirs, which reproduced this letter:

Dear Friend of Mine: Do you remember our meeting at the Ingleside jail, where you visited me? You did not ask me if I were guilty, or if I wanted to go to work, or if I thought I could make good. You said, “What can I do?” I told you that I was plastered over with prior convictions…I told you I was a complete criminal and glad of it. I’ve often wondered what the judge said when you approached him for me. He probably thought you were crazy. You got my sentence changed from twenty-five years to one year. When I first met you, my mind was closed against any kindly impulse. When I came back from the year in Quentin, my mind was open. I went to you, and then to your country place for six months. It is the only six months of my life that I would care to live over again. And one day when you said you had a job for me in town, I was surprised to feel that I rather liked the notion of going to work…

 Policemen, prosecutors, judges and jurors will read your story. Tell them the time to start helping the so-called criminal is when he is arrested, not when he is released. The “crime” thing is just a boil on the social body. I think it can be corrected, but they will never do it by opening it with a poisoned lance. They are all wrong, and are making it worse.


                   Jack Black,

             Reconstructed Yegg.

Burroughs with Kurt Cobain:

Like William Burroughs’ success late in life, giving readings on stage in New York punk rock clubs and recording albums with the likes of Thurston Moore, Kurt Cobain and Bill Laswell, Jack Black the San Francisco con spent his last few years giving talks on the subject of crime and prison reform, before large audiences of academics, rubbing elbows with legal geniuses like Clarence Darrow…surely a gratifying postscript to his surprise success as an author, a former stick-up man now dispensing wisdom to the American elite. While on a speaking tour in the east, Black wrote some final letters to Fremont Older back in “Frisco”:

My Dear Fremont: It’s about time that I reported. I found myself quite well known here through You Can’t Win and could be going about all the time if I weren’t so anti-everything… How I miss you and the gang on the Call…I am sure I could make a living here…Had lunch at the New Republic…they invited me to submit an article for the N.R. which I am doing now…

 You have certainly sent me along. For me to criticize N.Y.’s Chief of Police in a high-brow magazine seems dangerously near success…

 You know I’m too hard-boiled to get excited about selling a story, and none of them may ever get printed so I’ll wait till I get a check before I start boasting. I had lunch at the Harvard Club the other day (this is boasting) and got by without burning any holes in the table cover…

 I’ve been going around some “lecturing” and find myself liking it…There was a time when I made a whole lot of money by keeping my mouth shut and minding my own business and now here I am doing just the opposite.

 Yours as Ever, John Black

So what did Harvard graduate, self-made criminal, lifelong junkie and avant-garde novelist William Burroughs get out of You Can’t Win? When 19-year-old Bill Burroughs shot a hole through a wall in his dorm, did his fellow Missourian Jack Black suddenly flash through his mind? Or when the bullet hit Joan in 1951? or when he was arrested for possession of heroin in Paris in 1958? He summed up Jack, his original literary hero, this way: “Would he have been better off having spent his life at some full-time job?

I don’t think so.”

William Burroughs Harvard 1936

Where Burroughs and his boyhood idol converge is at the point where minding-one’s-own-business converges with the freedom to travel, to find satisfaction as a loner…converging with the dream of a little place of one’s own on the far outskirts of town…with the freedom to shoot a duck whenever one feels like doing it…with the desire to live dangerously, to commit a crime and get away with it, to make the easy money. It’s the western American dream as old as the hobos.

“To us lone cats,” Burroughs said, while quietly living out his last years in Lawrence, Kansas, “all supermarkets look the same.”

“Where are the hobo jungles,” Burroughs wrote, “the hop joints, the old rod-riding yeggs, where is Salt Chunk Mary? Where is the Johnson Family?” Burroughs, who referred to himself as The Old Writer in one of his late novels (The Place of Dead Roads) concluded wistfully: “As another thief, Francois Villon, said: ‘Where are the snows of yesteryear?’”