Honestly this is something that is so broad that it's nearly impossible to pick a top five, but here are five of my favourites which may or may not be top five, idk. Comparing mediums is also insanely hard.

The Lord of the Rings (books)
The Raven series (books)
The Longest Journey/Dreamfall series (games)
The Shawshank Redemption (film)
Lawrence of Arabia (film)