“If there are no stupid questions, then what kind of questions do stupid people ask? Do they get smart just in time to ask questions?”

Source: Novels, Squeeze Me (2020), Chapter 28

"Berzerk"
2010s, The Marshall Mathers LP 2 (2013)

Source: Beyond This Horizon (1948; originally serialized in 1942), Chapter 2, “Rich Man, Poor Man, Beggar Man, Thief—”, p. 35; see also pages 31, 33

Source: Philosophy and Real Politics (2008), p. 17.

Teaching as a Subversive Activity (1969)
Context: We can justify the list we will submit on several grounds. First, many of these questions have literally been asked by children and adolescents when they are permitted to respond freely to the challenge of "What's Worth Knowing?" Second, some of these questions are based on careful listening to students, even though they were not at the time asking questions. Very often children make declarative statements about things when they really mean only to elicit an informative response. In some cases, they do this because they have learned from adults that it is "better" to pretend that you know than to admit that you don't. (An old aphorism describing this process goes: Children enter school as question marks and leave as periods.) In other cases they do this because they do not know how to ask certain kinds of questions. In any event, a simple translation of their declarative utterances will sometimes produce a great variety of deeply felt questions.