Books: Plato's Republic (mostly interesting for a deep dive in the Socratic method, but also interesting to see where some modern ethics and philosophy is derived from in western traditions)

Go ask Alice (first real experience with experiencing what it's like to be truly a victim of abuse and addiction)

Flatland (great book about challenging fundamental assumptions!)

Think like a Freak (Really got me wanting to better analyse and thing about the world around me)

Harry Potter and the methods of rationality (great fanfic overall, but what really stuck with me was challenging my own conclusions after new evidence comes in, I really had to take a break and just think about that for a bit while reading this one)

Movies: The Trotsky (sleep on film that really explored being weird and asking the why not give people more control over their lives)

Game: Morrowind (First game that let me just ruin the plot and keep going, as a kid it probably one the most formative moments of really feeling like I had autonomy)

Edit: Spelled the movie wrong!