The Studs Lonigan trilogy, by James T. Farrell was included in Modern Library's list of the best 100 novels, which is how I ended up reading it. Like many of the books I write about, Studs Lonigan is one that you probably won't like, but will learn from. I honestly don't seek out painful books to read. They just seem to come to me.
The three books are titled Young Lonigan, The Young Manhood of Studs Lonigan, and Judgement Day, and are easily found bound together, so you don't have to search for each one. I love these pulpy covers though.
The Studs Lonigan books were written during the depression and follow the brief course of the life of one William "Studs" Lonigan, starting with his graduation from 8th grade in 1916, and ending with his early death of pneumonia in the early 1930's.
All three novels are set in the Irish-American neighborhood on the south side of Chicago. At the beginning, the story is hopeful. There's a scene in which Studs' father, Patrick Lonigan, complacently muses about his success as a parent and provider and the bright future ahead for his family. The family is lower-middle class; owners of a painting business. Paddy and his wife make it a priority to obtain a good Catholic education for their children and to raise them as directed by the Catholic church.
Studs himself is a decent kid. He likes to think of himself as a tough guy, he has a crush on a neighborhood girl, athletic talent, and adequate intelligence. So what goes wrong? According to wikipedia, Farrell intended to show the spiritual and cultural poverty that was ruining (and continues to ruin) vulnerable Americans. That first summer after eighth grade, Studs does nothing but hang around with a questionable group of boys. He admires the uncouth young men who hang out at the neighborhood pool hall. His parents, who claim to value education, give him no useful direction. (This is a particularly uncomfortable book for the parents of teenagers.)
In the second volume, he's a high school drop out and one of the regular members of the pool hall, where the young men do nothing but brag about their sexual exploits, bully the neighborhood misfits, drink, and air their prejudices. Indeed, there are so many racial and ethnic slurs in The Young Manhood of Studs Lonigan, I was nervous about reading it on my lunch break in case someone peeked over my shoulder. By the start of the third novel, Studs' health is a wreck and the Great Depression has cut off any chance he might have had to make something of himself.
A recurring theme is luck. Over and over, Studs waits for the day when his luck will change, and curses his own bad luck, but never does anything to help himself. He makes one bad decision after another (dropping out of high school, asking a girl he doesn't like to marry him, investing his savings in questionable stock). He has enough insight to regret his stupid actions after the fact, but not enough moral energy to change his ways. Paddy Lonigan's continuous lament is that he has worked hard all his life and now faces ruin and the death of his oldest son. He and those in his community consistently blame others for the decline of their way of life, and while the Depression isn't their fault, but they choose to place the blame on those of other races, religions, and ethnicities.
I read Studs Lonigan during the height of the media coverage about the violence at Donald Trump rallies and it's easy to find similarities between Trump supporters and Studs Lonigan and his friends. In both cases, they're people who have been left behind. We now live in a vicious, competitive meritocracy, where everyone seems to be fighting to be (or position their children) near the top. The affluent can obtain what is necessary to stay afloat and others can't and are lost in a world of disappointed expectations and resentment. And, as in Studs Lonigan, the blame is misdirected at specific races and religions rather than where it belongs. Although it was written over seventy years ago, the Studs Lonigan trilogy is a timely book to read now.