I found a very accessible/non-threatening introduction to philosophy is the book Sophie's World by Jostein Gaarder. Although its fiction, it covers a wide range of philisophical greats, and the story itself is structured around the nature of reality, and even makes the reader wonder what the nature of their own reality is; well it did me, anyway.
The film The Matrix also asked about the nature of reality (I walked out of the cinema wondering if VR could really fool us so convincingly, shame they screwed it up on the sequels!). Im sure there are plenty of other examples.
Unfortunately middle age has kind of kicked the philosipher out of me somewhat, no time to rhuminate...
Ah yes, Sophie's World was how our Philosophy teacher in high school introduced us to a wide variety of philosophers. I enjoyed watching it in class.
The Matrix is a very great philosophical movie, and sadly I have to agree with you that the sequels were not good. Part 1 is definitely among one of my most favorite movies. :D
It seems that, although we are not always aware to which philosophical thought our ideas belong to, we cannot escape that we too have subscribed to a personal philosophy.
Oh yeah, and OpenCulture's guide to philosophy movies is really great place to start your thinking too! http://www.openculture.com/2014/10/44-essential-movies-for-the-student-of-philosophy.html
What a coincidence - I just added a link to the Existential Comics' guide to studying philosophy as an amateur, which is actually a serious and seriously good guide: https://steemit.com/philosophy/@dphilosopher/existential-comic-s-guide-to-studying-philosophy-as-an-amateur
I also did a couple of podcast episodes to help people wanting to study philosophy independently:
Establishing A Philosophy Reading Practice
Keeping A Philosophy Notebook Or Log
And an episode on how to run a philosophy discussion:
How To Run A Philosophy Salon
Enjoy Truthseekers!