Eternal Sunshine of the Spotless Mind
Without spoiling anything, this movie is a reverse memory sequence of two lovers as their love ages and sours. It feels like watching your life (with someone) flash before your eyes, and induces a kind of existentialism that motivates me to choose a better (more intentional) version of connection with people than the complacency that settles in when you mesh someone with your life. This is a flavour of Death anxiety and Existential crisis that I quite enjoy, and that I'd like to feel semi-regularly (without falling into the trap of ruminating on it, of course).