Chicago has been the inspiration for so many of the great American novels of the early twentieth century. Gritty realism, after all, was the prevailing aesthetic of that era, and no place lent itself better to gritty realism than the Megalopolis of the Prairie. Here are a few personal favorites that I feel best convey the essence of the city around the time at which City of Scoundrels takes place.
1. Sister Carrie (1900) by Theodore Dreiser: This is truly one of the monuments of modern American literature. Dreiser’s prose can be awkward and pedestrian at times, but no other American author better captured the sweep of modern urban life and the inexorable social forces behind it. This novel about a naive young woman’s rise (and her wealthy lover’s equally dramatic fall) offers a picture of Chicago as a place where the line between brilliant success and abject failure can be very thin indeed.
2. The Titan (1914) also by Theodore Dreiser: The second book in a trilogy (but one that certainly can be read alone), this novel is loosely based on the life of Charles Yerkes, the powerful and corrupt financier who nearly gained control of Chicago’s entire mass transit system in the 1880s and ’90s. It’s a masterful exploration of the financial skulduggery that shaped the city’s development as it grew from a regional capital into one of the world’s great metropolises. (And, at the risk of making this list too Dreiser-heavy, readers might also try his less-known second novel, Jennie Gerhardt (1911), which may actually be his most approachable book.)
3. With the Procession (1895) by Henry Blake Fuller: Fuller, born and raised in Chicago, deserves to be more widely read than he is today. He’s best remembered (when remembered at all) for The Cliff-Dwellers, one of the first novels about life in skyscrapers, and Bertram Cope’s Year, one of the first novels with a homosexual theme. Even so, I find this 1895 book to be his most compelling work, at least from the perspective of Second City history. It’s the story of a successful and good-hearted Chicago businessman undone by his profligate children, whose vain social ambitions all but destroy the family fortune.
What We're Reading This WeekGet recommendations for the greatest books around straight to your inbox every week.
4. The Jungle (1906) by Upton Sinclair: Perhaps the quintessential muckraking novel, this polemical (but surprisingly readable) screed is a book that you were probably forced to read in high school. ￼￼But it’s worth a second look. Sinclair’s depiction of the sordid conditions in Chicago’s meatpacking industries shocked the country when the book was first published in 1906. President Theodore Roosevelt, who hated Sinclair’s socialist politics, nonetheless could not deny the accuracy of his reporting. After a federal investigation confirmed the author’s findings, Roosevelt signed the Meat Inspection Act and the Pure Food and Drug Act of 1906—proving that sometimes literature can change the world. (The book also provides a tell- ing look at the life of Chicago’s working-class immigrants at the turn of the century.)
5. The Pit (1903) by Frank Norris: Chicago’s world-renowned Board of Trade might seem an un-likely setting for a novel, but Norris’s The Pit brings the high-stakes maneuvering of the grain-futures market to vibrant life. Of course, there’s a romantic subplot, as the pretty wife of one of the market’s heaviest hitters becomes involved with a dreamy-eyed artist (he can whisper po- etry in her ear, while her much older husband can speak of nothing but three-month wheat contracts). But the real juice in the novel flows from the grinding wheels of speculative capital- ism, when the husband makes a reckless attempt to corner the world wheat market – with predictably disastrous results.
6. Native Son (1940) by Richard Wright: A mas- terpiece of literary naturalism, Wright’s novel, loosely based on an actual incident, tells the story of a poor young black man who accidentally kills the daughter of his wealthy white employer. The depiction of life in Chicago’s 1930s African American ghettos is sobering, and the plot moves with a momentum that is as believable as it is relentless. A powerful look at the world left behind by the 1919 race riot.
7. So Big (1924) by Edna Ferber: A much sunnier book than the others on this list, this Pulitzer Prize–winning novel does a wonderful job of exploring the relationship between the city of Chicago and the agricultural hinterlands that sus- tain it. Against long odds, a fiercely independent Dutch-immigrant woman makes a life for herself in the rich farmlands south of the city, succeeding both financially and spiritually—until her misguided son gets tangled up in the luxurious but superficial life of Chicago’s moneyed elite. Contains some of the best physical descriptions of Chicago in our literature.
8. Studs Lonigan: A Trilogy (1932–35) by James T. Farrell: Writing with the clinical perception of an anthropologist and the sympathetic insight of a first-rate novelist, Farrell traces the downward trajectory of a tough Irish kid growing up on Chicago’s South Side. Never straying far from the narrow perspective of its troubled and psychologically limited protagonist, this series of three novels can seem claustrophobic at times, but there is no better record of what it was like to be a working-class Irish Chicagoan in the first decades of the twentieth century. For readers of City of Scoundrels, the chapters relating Lonigan’s experience during the 1919 race riot (he belonged to one of the rampaging Irish gangs that were causing much of the trouble) will be especially interesting.
There are so many other good – and some less good but still enlightening – Chicago novels set in roughly this time period that I can’t end without briefly mentioning a few more: The superb U.S.A. trilogy of John Dos Passos (especially the novel 1919) ranges all over the country and throughout Europe, but some of its best plotlines weave through Chicago; Erik Dorn, by the brilliant Chicagoan Ben Hecht, is a deeply flawed and callow novel, but it’s definitely worth reading (though his play about Chicago journalists, The Front Page – written with Charles MacArthur – is a lot more fun); Meyer Levin’s The Old Bunch is in many ways like a middle-class Jewish version of Studs Lonigan; Levin’s Compulsion, a fictional retelling of the notorious Leopold and Loeb murder case, is also worthwhile; and although I personally find Sherwood Anderson unreadable, others admire his early Chicago novel Windy McPherson’s Son.
Meanwhile, to switch genres for a moment, any student of Chicago history really must read Carl Sandburg’s Chicago Poems, which are often creaky and over-earnest, but never less than evocative.
And for perspectives on the Chicago of more recent times, there’s Trumbull Park by Frank London Brown, Knock On Any Door by Willard Motley, The House on Mango Street by Sandra Cisneros, and, of course, the novels of Nelson Algren and Saul Bellow.