To write about Benjamin in terms of Nietzsche. I remember that a description of some event in Sartre’s autobiography ends with a line to the effect of “and that’s what finally cured me of my idealism.” I think this sheds some light on why it’s hard to bring Benjamin into contact with Nietzsche. Is this even possible? I think Sartre may have been lying to himself here, but it seems like Benjamin never even had the pretense of experiencing something like this.
Benjamin saves up all of his optimistic power for minute or fragmented things, so that he can invest them with his messianic and mystic brand of hope. What kind of faith is required to do this in total seriousness? Let’s be reductive and say that it takes some kind of idealism. Benjamin is an optimist insofar as he’s a materialist: he really does find hope in things. But materialism—historical or otherwise—isn’t material, it’s an idea. I'm questioning Benjamin’s ability to re-present things clearly (or objectively?)...
It seems like Nietzsche goes a lot farther than Benjamin in terms of optimism. Benjamin tacks his on after establishing that the world is a melancholy place, but Nietzsche is hopeful from the beginning. He's not concerned with the value of phenomena in themselves, much less granular ones like the ones Benjamin studies. And unlike Sartre, I’m pretty sure that he’s not an idealist.
Maybe the gap between these two can be explained by saying that Benjamin deals with experience and Nietzsche deals with being. I think there’s something more to it, though. They don’t go together, despite the fact that there are other writers, like Borges and Kafka, who can be easily read alongside either one. (Borges might be faking his appreciation of Nietzsche, but at least he didn’t make that his marketing strategy.)