Like many others in the comments, I loved Infinite Jest, for many reasons, but just to go into one in particular, I feel like David Foster Wallace’s viciously smart, sardonic, ironic, and often deeply depressing sense of humor is at its peak in IJ. There are so many things from the book that stick out to me as being memorably funny: the woman with an artificial heart who dies because a purse snatcher takes it, chasing the snatcher for several blocks while yelling, “Stop her, she’s stolen my heart!” while onlookers laugh and think it’s just some sort of couple’s tryst; the party for someone’s dissertation defense where a bunch of pretentious academics are all doing this kind of anti dance consisting of moving as little as possible so as to look like you’re not dancing, but with a kind of jerking rhythm; the description of the 90s TV special about a guy with paranoid schizophrenia afraid that the government wants to inject radioactive fluid into his brain and that he’s being chased by giant machines that will eventually catch him and consume him, who for science is injected with a radioactive solution for a PET scan and then stuck into the giant whirling scanner, a look of horror on his face as he sees his worst fears coming to life; the Canadian government minister who dies because he has a cold and cannot communicate with the person robbing his house that he cannot breathe through his nose; the teen tennis player who wears all black and is called The Darkness, meanwhile the other teen tennis player who tries to get people to call him The Viking but no one does; the whole thing with the wheelchair assassins and “to hear the squeak”; the absurdity of Helen Steeply and the even more ridiculous absurdity of Orin falling for him/her; Avril losing her shit and running around the yard with the mold her son ate held aloft, screaming for help; and so on.

Plus this all often leading into scenes that are just relentlessly tragic. Joelle freebasing way too much cocaine in the bathroom at that same party; Poor Tony winding up having a seizure and swallowing his tongue on the T; the viscerally accurate depiction throughout the book of addiction and depression; Joelle’s entire life story; Himself’s slide into madness and suicide while basically no one tried to help; the short bit of Himself talking to his alcoholic father when he was younger; and so on.

In a way it reminds me of the show Bojack Horseman, with the mix of high brow and low brow humor, unflinchingly dark narrative, and deeply flawed characters.

All of which is to say: it’s not always an easy book, but it’s definitely worth at least two reads, one to get the story and another to appreciate all of the interleaving of the various stories throughout the book.