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In recent decades, parenting seems to have become an increasingly all-consuming project, particularly in affluent and highly educated families. Yet, those same decades have also seen a dramatic increase in the number of adults—and especially affluent and highly educated adults—who are choosing to forgo parenthood entirely. This paper investigates that paradox of modern, privileged parenting. Specifically, we use a content analysis of New Yorker cartoons from 1925-2006 to examine portrayals of children and childrearing. In doing so, we find that portrayals of children and childrearing are both more varied and more fluctuating than existing research would suggest. Contemporary cartoons celebrate children, but also recognize the significant challenges children create for parents. Cartoons from the 1920s and 1930s—when rates of childlessness were also high—reveal a similar set of mixed attitudes. In light of these findings we argue that when childrearing poses particularly high costs to parents, and when those costs are widely recognized, reluctance about parenting can easily lead to opting out. We discuss the implications of these patterns for research on children and childhood, research on popular parenting patterns, and research on changing demographic trends.