Watchmen is amazing. It's a graphic novel (so I don't know if you're into that) but there is plenty of meaning everywhere you look and it's incredibly deep and philosophical. Also I think it's really relevant right now as super heroes are everywhere and the novel is a character study on how we perceive super heroes vs how they truly are (really ****ed up) and breaks down the genre.
If not, I would suggest Doubt, either the play or movie (but mostly the movie). It's about whether or not a catholic priest molested a child. The whole point of the story is that they don't specifically tell you if he did it or not, it's up to you to form your own opinion. But there is plenty to analyze, like the use of light/lamps, sound and recurring motifs that may sway your opinions one way or the other
