Waking Life is a pedantic, self-serving film. Sure, it may look good and the style is certainly enjoyable if you're very high, but I'm afraid no amount of drugs could make this boring film anything more than what it is: hipster bullshit, which is an odd term to use, considering the film's release in 2001 pre-dates the current hipster trend of 2011 by a decade, give or take. Nonetheless, strip away all the stylised rotoscoped imagery and one is left with an almost indecipherable mess of words, ideas, and theory so convoluted it makes the average benzodiazepine-induced stream-of-consciousness babble look like the goddamned Path to Enlightenment. Waking Life is almost painful to sit through. The lack of plot and over-indulgence of pseudo-intellectual nonsense may help to give the "dream within a dream" feel, but it's all just smoke and mirrors, hiding any real substance. It is, in effect, "a tale told by an idiot, full of sound and fury, signifying nothing." (Shakespeare, "Macbeth", act 5, scene 5)
Drop three tabs of LSD and go to a coffee shop heavily populated with hipsters and goatee-sporting liberal art majors for three hours. Ta-da! You've experienced Waking Life.