Both Collingwood and Wittgenstein link philosophy with poetry. Collinwood thought that “good philosophy and good poetry are not two different kinds of writing, but one,” while Wittgenstein wrote that “philosophy ought to be written only as a poetic composition.” In this chapter, I present what these two philosophers say about the relation between philosophy and poetry and argue that, their differences notwithstanding, both want philosophers to express their times, just like poets, and lead their audience to the future in a process of self-knowledge and reform. Finally, I comment on Richard Rorty’s remarks on the relation between philosophy and poetry. I argue that, unlike Collingwood and Wittgenstein, Rorty wants poetry to replace, and perhaps even eliminate, philosophy, but agrees with them and Nietzsche that poets ought to act as prophets, not in the sense of foretellers, but in the sense of inspiring leaders and groundbreakers.