Wittgenstein's attitude to writing philosophy is an important part of his complex legacy from Frege. Even the frequently misconstrued phrase, "Philosophie dürfte man eigentlich nur dichten", is part of that legacy. How should we actually render that sentence in English? How is the idea that Dichtung is a necessary aspect of philosophical method rooted in thoughts that ultimately find their way back to Frege? Where do we find Dichtung in the so-called private language argument? How is Wittgenstein's view of the role of Dichtung in philosophy related to his appreciation of humor in philosophizing? What is the role of humor in Frege's work? How does Wilhelm Busch in Eduards Traum illustrate the philosophical significance of humorous Dichtung? What is the link between Dichtung and craftsmanship in writing philosophy for Wittgenstein? These are the central issues that the article addresses.