Ludwig Wittgenstein suggests that "A serious and good philosophical work could be written consisting entirely of jokes". The idea for this dialogue comes from a conversation that Michael Peters and Morwenna Griffiths had at the Philosophy of Education of Great Britain annual meeting at the University of Oxford, 2011. It was sparked by an account of an assessment of a piece of work where one of the external examiners unexpectedly exclaimed "I knew Jean-Paul Sartre", trying to trump the discussion. This conversation is a dialogue about comedy and humor as a basis for philosophy, education and pedagogy that provides an introduction to recent works and a context for ongoing research. The concluding section provides further reflection on some of the main themes, drawing attention to the significance of humor in dialogues within philosophy and education, and suggesting that it has a particular role in resisting managerialism at all levels of educational institutions.