The Books That Taught Author Courtney Maum How to Be Funny Without Being Cruel

Growing up in Greenwich, Connecticut during the 1980s, I was no stranger to the venomous way wealth was portrayed in fiction and in films. Spouses who detested one another, siblings who’d stopped speaking, substance abuse issues a-go-go, nannies groomed for second wifedom, status symbol pets. Writers assigned to me in high school like Updike and Roth explored wealth and privilege with bleakness and depression—if there was any fun, it was alcoholic or philandering. Usually, it was both.

It’s not that I didn’t appreciate this upper crust fiction, it just didn’t leave room for the joy and absurdism that I saw all around me. I was 13 when I attended a holiday party where the hostess flooded the first floor of her mansion so that the attending children could ice skate through the rooms. Another party in the same gated development saw giraffes in the backyard during a fundraiser for some zoological concern.

Once I graduated high school, I started looking for writers wh...