In my book Making Up Your Mind about Waking Up Your Mind I cover a few movies that portray the process of mental awakening in a way I have practical experience with.
Besides those movies, there are several others that I found useful at various stages in the process of 'getting it'. They all point in the same directions, but do so from a different angle.
Some movies are about the challenge of owning all of your habits, desires and preferences despite the opinion of others or the consequences.
Some are about overcoming the paradox of how to let go of control without really being in control of the letting go – how to get past the wanting to not want to want anymore that is inescapably part of mental awakening.
Some are about how you make decisions (or even run a country) every time you pass the mental awakening barrier. It shows how the interplay between intellect and intuition changes.
Others might just show metaphorically how our minds get trapped gradually into taking concepts for real.
Here's the list: