This chapter spans the attitude toward laughter, self-referential laughter, humor, and cheerfulness, good humor or gaiety in philosophy’s early modern and modern periods, from the sixteenth century (Michel de Montaigne) to the eighteenth century (Johann Georg Hamann). A notable follower of Erasmus of Rotterdam also in matters of humor as an umbrella term, Montaigne innovates in seeing all human beings, oneself included, as laughable (Homo risibilis). I trace his influence on the views of laughter, self-referential laughter, and gaiety held by various philosophers, moralists, and philosophes of the seventeenth and eighteenth centuries. I follow by emphasizing the novelty of Benedict Spinoza’s thought on laughter, joking, and cheerfulness against the background of his epoch and tracing his probable influence on the Enlightenment benign view of humor. I describe the unalloyed defense of humor and of good humor or cheerfulness that the third Earl of Shaftesbury advances, as well as the association of humor and ridicule with truth that he introduces in philosophy. Finally, I trace the immense influence he had, also on the 200 years controversy about the relation of ridicule with truth to which many contributed in the eighteenth and nineteenth centuries, including Hamann and Søren Kierkegaard.