The movie "Waking Life" is a philosophical masterpiece: a quasi non-narrative psychedelic dreamscape exploring the very nature of both existence and non-existence in unpredecented depth.
In a sequence of seemingly unrelated dialogues, the film addresses anything from the nature of love and death to the paradox of free will, starring three philosophy professors (Louis Mackey, Robert Solomon & David Sosa) and several other contemporary philosophers (Eamonn Healy, Aklilu Gebrewold, Caveh Zahedi, Timothy "Speed" Levitch, ...), summarizing the best of European, Asian and African philosophy alike.
Waking Life is by far my favorite movie; and I can't think of even a single movie that comes remotely close to the philosophical depth that I find in Waking Life. Can you? Or to phrase it differently: can you recommend any movies similar to Waking Life?
Of all the movies I've ever seen so far, The Congress is the one I know that is close to "Waking Life" and "A Scanner Darkly" (that other animated masterpiece by Linklater) both from an audiovisual perspective and from a philosophical perspective.