He applied the "Page 99 Test" to his most recent book, Norman Rockwell: The Underside of Innocence, and reported the following:
Page 99 occurs in the middle of an especially weird chapter, on Norman Rockwell’s portrayals of children. Here I’m discussing a painting in which Tom Sawyer is getting flogged by a schoolmaster, who has picked Tom up, slung him over his thigh, and begun whacking away at his bottom. We don’t allow flogging today, and it was always a bit depraved. Rockwell’s portrayals of children, like this one, are often edgy and strange:Read an excerpt from Norman Rockwell: The Underside of Innocence and learn more about the book at the University of Chicago Press website.
The looming schoolmaster, switch poised to strike (several broken ones already litter the floor) holds a screaming Tom aloft as he prepares to deliver another blow to the boy’s derriere. The girls look on in sorrow while the boys watch the whipping with unconcealed glee. A blood-red kerchief which emerges from the schoolmaster’s backside (and matches the dress of the girl at bottom right) embodies in its color the violence of the moment, and makes it look, oddly, almost as if the schoolmaster bore welts on his backside. This illustration, like many of Rockwell’s, owes a debt to the tradition of Dutch genre painting, such as a painting by Jan Steen depicting a schoolmaster rapping a young, weeping boy on the palm with a spoon. (Among Steen’s onlookers, it is a girl who, interestingly, seems most to enjoy the spectacle of punishment.)
Whipping had, of course, been a staple of education for centuries. The assumption of the painting, I think, is that it is an essentially harmless and quite possibly character-building practice. Sometimes rambunctious boys just need a good tarring. Good behavior enters through the rear end. But on the other hand, schoolmasters were sometimes appallingly cruel, and their paddling of boys’ bottoms took on a sadistic, even sexual cast. The renowned Renaissance schoolmaster Richard Mulcaster, for instance, made liberal use of his birch rod, which he named “My Lady Birchley.” Mulcaster jokingly referred to beatings as marriage ceremonies between his Lady Birchley and his students’ buttocks. Thus the practice of whipping could–and often did--take on a perverse character. And this ambiguity of whipping, which employs a young boy’s bottom either for punishment or for pleasure in punishment, acts as the hinge on which the disavowal of Rockwell’s painting turns.
In my book I argue that America’s Favorite Illustrator has been badly misunderstood by both his fans and his detractors. Rockwell is not culturally or artistically naïve. Above all, he does not portray a bland style of American innocence. Rather, he is a canny diagnostician of innocence, which he exposes as a fiction based on various forms of denial and disavowal. Rockwell fills his apparently mayonnaise world with dark and disturbing details which he then dares the viewer to acknowledge. In exploring the underside of Rockwellian innocence, however, I do not aim to denigrate Rockwell or his work. Instead, I try to show that he’s a smarter, more complex and more accomplished painter than people generally recognize. His work is challenging in ways that we have yet to face.