I just discovered that the Open Culture weblog has created an addendum to Matt Whitlock’s Essential Movies for a Student of Philosophy list that’s been hanging out in my bookmarks for a couple months.
One extra title that I might suggest is Spike Jonze’s Adaptation, and not just because of the New Yorker magazine connection. I am just a sucker for Charlie Kaufman movies.
See also: 16 mindfuck movies, compiled by Matthew Baldwin.