This essay highlights the narrative dimensions of philosophical argumentation in two foundational texts: Walter Benjamin’s ‘Critique of Violence’ (Zur Kritik der Gewalt) and Ludwig Wittgenstein’s Tractatus Logico-Philosophicus (Logisch-philosophische Abhandlung), both first published in 1921, when Benjamin was 29 years old and Wittgenstein was 31. Besides examining the narrative structures or scenarios of these two philosophical texts, the essay suggests that they do not solve the issues they raise; finally failing to reach a definitive, affirmative conclusion. Therefore, both Benjamin (indirectly) and Wittgenstein (more openly) have to confront the inherent difficulties of accomplishing the task (die Aufgabe; a term they both use) they have set up and attain their final performative gesture by affirming failure, producing an unresolved, but what could also be seen as a creative tension between their narrative and philosophical closures. Approaching affirmation from the perspective of failure paradoxically provides a degree of certainty which a straightforward affirmation–which can be proven wrong or too hasty–cannot bring about. Failure, being final, generates a certainty which success does not achieve.