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?

Edit :

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.

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    I love that movie, but it is not just a movie about philosophical ideas. It is also a movie about the fascinating phenomenon of Lucid Dreaming, and it does a fantastic job depicting it.
    – nir
    May 24 '16 at 9:45
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    It's not another Waking Life but you might enjoy the excellent Speed Levitch documentary The Cruise. May 24 '16 at 13:22
  • How about all of Woody Allen's movies combined? youtube.com/watch?v=Jbnueb2OI4o
    – nir
    May 24 '16 at 13:27
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    "Is the Man Who is Tall Happy?" is an interview with Noam Chomsky. It has a certain overlap both in style and in the nature of its content.
    – user9166
    May 24 '16 at 16:26
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    Funny. I was going to mention "The Congress" until I read your edit. There's also "The Fountain" if you're looking for similar qualities in film, but Žižek's Pervert's Guide (1 on Cinema, 2 on Ideology) are more explicit works of cinematic philosophy, as answered below.
    – Ryder
    May 25 '16 at 13:51

Waking Life is somewhat sui generis, but I would highly recommend "The Possibility of Hope," a documentary by Gravity director Alfonso Cuaron, included as a DVD extra with his incredible Children of Men. Depending on your opinion of Slavoj Zizek, you might also enjoy his "Pervert's Guide to Cinema." A movie that is less explicitly philosophical, but that shares some similar themes of reality and identity (as well as a certain psychedelic sensibility) is the Gondry/Kaufman classic "Eternal Sunshine of the Spotless Mind."

If it was the style of the film that appealed to you, I can't immediately identify any full-length animated films that are comparable, but there are some excellent philosophical shorts, including More, Vrykutasy, and Balance. There's also Don Hertzfeldt's Everything Will Be OK and World Of Tomorrow.

  • From a philosophical perspective, I prefer "Human Nature" to "Eternal Sunshine of the Spotless Mind". It has the same Gondryesque humor, but it goes a bit deeper into the more interesting aspects of... well... human nature. I can't say I've ever heard of "The Possibility of Hope" or "Pervert's Guide to Cinema", so +1 for these suggestions ;-) May 24 '16 at 14:19
  • Kaufman is always good for an intellectual workout. His Synecdoche, New York is another one that takes on the meaning of reality. I've also heard good things about his new Anomolisa, but I haven't seen it myself. May 24 '16 at 14:35
  • I'm not really that much into Charlie Kaufman. I'm more into directors like David Cronenberg (eg. Cosmopolis), Darren Aronofsky (eg. Requiem For A Dream) or Terry Gilliam (eg. Tideland). Feel free to check out my personal top 100 May 24 '16 at 14:46
  • I added some animated shorts to the above answer. May 24 '16 at 15:33
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    Ever seen The Congress? Of all the movies I've ever seen so far, it's the one I know that is closest to "Waking Life" and "A Scanner Darkly" both from an audiovisual perspective and from a philosophical perspective. May 24 '16 at 15:36

In the spirit of providing an answer to your question rather than adding to the pile of everyone's favorite philosophically-minded movies, please a take a moment to review The Cognitive Science Movie Index. Although the aim is CogSci and not philosophy specifically, it could be argued that all cinema is anyway always already a reflection of philosophy.

Since you mentioned Waking Life specifically, and indicated your interest was directed more at movies with explicit or more immediately relevant themes and concepts, The Index will likely be right up your alley— Waking Life is included in the list as well, and there is a severe amount of overlap between the fields. The site was originally referred to me by Rob Goldstone at a conference on just such a crossover, regarding the concept of cognitive penetration.

I'd recommend to anyone interested in this question, adding your own finds to the list and helping it grow.

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