"Miss Lonelyhearts" by Nathanael West (1933)

Does a 50-page novella count as a book? If it does, my god, this one is bleak. Russian literature is (hilariously) stereotyped as bleak but within the first three pages of this one we're already exposed to depression, helplessness, Christ, sickness, abortion, suicide, mental disability, and rape—I don't recall Chekhov ever overloading his first act gun in quite the same way. The novella is also a weird, jittery comedy (how West achieves this is nothing short of a miracle.) This is the premise: A New York newspaper advice columnist receives daily pleas for help from desperately lost people with very serious problems; the combination of being exposed to the worst of humanity along with the fact that "Miss Lonelyhearts" (a stepping-stone gig taken by an ambitious, and very flawed, 26-year-old reporter) is viewed as a sort of unerring savior by the entire city completely batters his ill-equipped, genuinely empathetic/genuinely violent psyche. Hilarity ensues. (There's actually a lot of similarity to a pitch-black Joe Orton farce; maybe West was an inspiration.) Four stars.