San Francisco has always embraced the weird, the outrageous, and the rebellious. From the raucous times of the Barbary Coast, to the howling poetry of the Beats, to the free love of the hippies, letting your freak flag fly is not just a slogan in the City by the Bay, but a way of life.
All of that uninhibited freedom, though, has at times fostered a sense of lawlessness in San Francisco. For every sailor who awoke in a brothel in the Barbary Coast, another awoke on a ship, kidnapped by “Shanghai” Kelly; while the Beats were reciting poetry in North Beach, Sonny Barger was forming the notorious Oakland chapter of the Hells Angels; and as the hippies were frolicking in Golden Gate Park, the Zodiac Killer was tallying victims all across the Bay Area.
It’s not surprising, then, that two great crime books to come from San Francisco were written by authors with checkered pasts. You Can’t Win by Jack Black, and Shake Him Till He Rattles by Malcolm Braly, were penned by career criminals who straightened out in time to capture their respective eras in San Francisco history. Though written decades apart, the books share a voice that is particular to that of an ex-con. It is a voice that is tough yet empathetic, unflinching yet forgiving. It is neither self-pitying nor self-flagellating. It is the voice of a life lived hard.
You Can’t Win, first published in 1926, is the autobiography of Jack Black, who was at various times a burglar, a convict, a dope fiend, a “yegg,” and a member of the Johnson Gang of thieves. Black crisscrossed the country at the turn of the 20th century, learning his craft (thieving, not writing) from a cast of characters so vivid, their names alone will make you smile: The Sanctimonious Kid, Salt Chunk Mary, Sticks Sullivan, Foot-and-a-half George, and Montana Blacky, to name just a few. After many visits to San Francisco, Black eventually settled down in the city, his decision no doubt influenced by his stay in nearby San Quentin prison.
Open to any page in You Can’t Win and you will see why it was the favorite book of William S. Burroughs, who wrote the introduction for the AK Press reissue. Black’s teeming prose, his rat-a-tat-tat rhythm, and his use of street slang are obvious influences on the Beats, especially Jack Kerouac. You Can’t Win is also stuffed with delightful old time colloquialisms: professional thieves were “yeggs,” cops were “bulls,” opium was “hop,” and everyone was addressed as “kid,” no matter their age.
Black tells us at the beginning of the book that he is going to write about the things he stole during his life as a thief just as he took them, “with a smile.”