I loved Infinite Jest, so naturally I loved Winesburg, Ohio. Sherwood Anderson is clearly David Foster Wallace’s doppelganger, displaced eighty years in the past, and two states away, but possessing a very similar melancholy sense of humanity, and even a kindred narrative style. The more I reflect on these two novels, the more parallels I find. One’s about drugs, entertainment, and sexual deviance in fast-paced urban Boston of the near future. The other’s about isolation, disappointment and sexual repression in the leisurely and pastoral Winesburg, Ohio of circa 1915. Their window dressings may differ, but their hearts are both pervaded with a deep sense of loneliness and disconnection. Unconvinced? Let me see if I can persuade you. While both novels tend to bounce around between multiple story threads, some of which connect up in unexpected ways, each has a frontrunner candidate for the title of protagonist. Hal Incandenza and George Willard are both intelligent young men, raised by distant mothers and successful yet frustrated fathers. Each stands on the doorstep of adulthood, raked with uncertainty about how to go forward, and scarred by upbringings which have left them poorly-equipped emotionally to form healthy adult relationships. Both books contain naïve young women betrayed by their lovers. Alice Hindman lies on her bed, staring nightly at the wall, waiting in despair for years, abandoned and forgotten by Ned Currie, who really only ever wanted to bed her and move on. Joelle Van Dyne struggles alone with addiction and the bittersweet memories of Orin Incandenza, who bedded her, disfigured her, and has definitely moved on. Infinite Jest has Don Gately- the perpetually despondent rehab counselor, whose past secrets (drug addiction and manslaughter) impede him from forming close interpersonal bonds. Winesburg, Ohio has Wing Biddlebaum, a perpetually introverted and fidgety recluse, whose past secrets (untrue accusations that he molested students as a teacher) impede him from forming close interpersonal bonds.Are these parallels too much of a stretch? Too reductive? Maybe these two novels aren’t as similar as all that.. but they do have common themes, and more than anything else, they both leave me with a sense that Nature and History have ganged up to play a cruel joke on many of us: making us on one hand genetically and socially conditioned to congregate in packs, but on the other hand shaping our society to be so rigidly hierarchical, so full of oppressive demands and expectations, and governed by such complex unspoken nuances of manner and custom that the whole process of socializing and getting along in large groups hardly feels achievable to many, and hardly seems worthwhile to many others. Most of us ultimately find a livable balance between inputs and outputs: a tolerable equilibrium between the mental and physical energy we must expend, and the social and material life that they buy for us. We don’t quite live out our wildest dreams, but we get enough of what we need to soldier on. Frequently this involves either accepting that we can’t "have it all", or redefining our idea of what "having it all" means.That’s great for those who make it, but society and economics are hard, and not everybody ends up with the "happy-enough" ending. Some people give up on the standard prizes… the proverbial 2.3 kids and the house in the suburbs with the white picket fence. They follow some other dream, God bless ‘em, and some find their own happiness. Hermits, starving artists, nuns, and other eccentrics essentially say "fuck it". They haven’t found conventional happiness, and they’re done trying. I’m not sure whether this represents victory or defeat. Regardless, this book isn’t about those people; this book is about the people who can’t seem to attain the orthodox version of happiness, but don’t have a better dream to replace it with. It’s people who can’t quite master the rules of social success, but can’t or won't reject mainstream civilization and its prizes either.They keep following society’s rules, knowing on some level that the game is rigged against them, but following nonetheless, because they lack either the courage or imagination to take another path. Consider Ray Pearson: miserably married for decades to the girl he got pregnant, in a fleeting moment of passion. Consider Elmer Cowly: painfully awkward and overly-self conscious, who leaves his family and a secure job to head off into the night, dreaming of a distant city, where he might "… get work in some shop and become friends with the other workmen and would be indistinguishable. Then he could talk and laugh. He would no longer be queer and would make friends. Life would begin to have warmth and meaning for him as it had others." God damn; is that the saddest thing you’ve ever heard? It’s not so different from the kids at the Enfield Tennis Academy in Infinite Jest, is it? Those kids leave their families to attend the prestigious academy, placing all their hopes for deferred happiness in the dream of a career in professional tennis,"…this game the players are all at E.T.A. to learn, this infinite system of decisions and angles and lines Mario’s brothers worked so brutishly hard to master: junior athletics is but one facet of the real gem: life’s endless war against the self you cannot live without." Fuck. Kill me now, if that’s what it’s all about.This isn’t a philosophy book, but it’s written by an observant and philosophical author. I don’t directly identify with any of the characters; I’m generally satisfied with my life, even if the review suggests otherwise. So why did these assorted vignettes about sad, disenfranchised characters touch me so? Probably because I think our social systems deserve to have their warts pointed out. They’ve evolved as a successful way to maintain order over time, which has some benefits for the community at large, but is frequently cruel and stifling to the individual, who may pay a high price for overrated things like acceptance and a sense of belonging. Sherwood Anderson seems to be telling the great abstract System that it’s not as fucking awesome as it thinks it is; and even though I’ve bought into it (or sold out to it) in many ways, there’s a part of me which still holds out against it, and which thinks the System deserves this tongue lashing, and probably a lot worse. -Thanks, David!