The question of what makes a film rewatchable is more interesting than the question of what makes a film good.
Some films are so perfectly calibrated to their own logic that the second viewing feels like watching them for the last time — everything falls into place, and there's a specific melancholy to knowing how it ends while still being moved by it. Chinatown is like this. The second viewing of Chinatown is a tragedy in a way the first viewing isn't.
Some films become more interesting the more context you bring to them. 2001: A Space Odyssey rewards every viewing because you're always bringing a different self to it. I was seventeen the first time I saw it and I thought it was boring. I was thirty-two last time I watched it and I thought it was one of the few genuinely spiritual experiences film has produced.
And then there's a third category: films that are perfectly satisfying once and add nothing on rewatch. They're not worse films. They're just complete in one viewing. The problem is when we use rewatchability as a proxy for quality, which we shouldn't.