Verdict: ★ ★ ★ ☆ ☆
There are films which you wish you had watched earlier in life, and there are others which don’t make sense until you have had your fair share of world experiences. Waking Life falls in the former category.
The college sophomore me would have been really excited about discussing vague notions of self and freedom and free will and morality and dreams - and don’t get me wrong, mid-twenties me is equally as excited about these things as my former self, if not more so - but the problem lies in the superficiality of it all. Now that I’ve had more nuanced discussions about these philosophical conundrums and have read a fair amount of academic literature, the surface level discussions here leave a lot to be desired.
Having said that, since I put Linklater on a pedestal, this by no means make it an average film. The visuals are cool, the animations are innovative and the ideas discussed, no matter how superficial, ultimately make you think and mull them over afterwards. That is more than what any filmmaker can aspire for and in the end, makes this a watch worthwhile for me.