Jake Cole’s review published on Letterboxd:
Socrates said "The unexamined life is not worth living," but WAKING LIFE suggests that it is impossible to live without self-examination, that dreams are a way to take a break from consciousness to ruminate on it. I saw WAKING LIFE when I was 18 or 19, freshly into film and suffering from an acute case of being a college freshman. I called it pretentious, pointless, self-absorbed, and all the other adjectives young people use without a hint of self-awareness when they confront something that is (at least for the moment) insurmountably difficult and decide to play a game of chicken instead of just backing down.
I'm mature enough now to be upfront and admit that a number of the treatises on matters of existentialism, postmodernism, the ontology of cinema, dreams, political theory and more can still leave me behind at times. But as philosophically oriented as the film is, it also has the ineffable spark of Linklater's best work, driven as much by a sense of warm curiosity as intellectual rigor. I love its diversions, from the black-comic digression of two gun-rights dudes ultimately offing each other out of carelessness to a chance meeting between a young man and woman that they decide to take as an invitation to really talk to each other to break the usual routine of just passing by with zombie pleasantries.
Linklater has circled around Joyce before: SLACKER occurs over a 24-hour day like Ulysses, and its relay structure could be loosely linked to Dubliners' collection of thematically, if not personally or narratively, related scenarios. BEFORE SUNRISE occurs on Bloomsday. WAKING LIFE, with its unending, infinitely layered series of dreams and dreams within dreams, matched by that gorgeous rotoscoping that colors humans outside the lines and adds action to their gestures and speech, obviously takes after Finnegans Wake. The Wake is endlessly more inscrutable than WL, which despite a few moments of complex discussion, is far more accessible than I could or would see six or seven years ago. But they both share an attempt, be it through fragmentary prose or this delightful animation, to capture that which is hardest to define, not in Freud/Jung terms of analysis but in the nonexistent, or at least impossibly knotted, logic of dream movement. As such, it is less something to try and "solve" than a passage that should be entered into willingly; go along with the flow, and it's surprising how damn entertaining it is, with more than a few laughs.
One of the characters in WAKING LIFE stresses to the film's HCE figure, "Our planet is facing the greatest problems it's ever faced. Ever. So whatever you do, don't be bored. This is absolutely the most exciting time we could have possibly hoped to be alive. And things are just starting." Linklater himself crops up in the film from time to time, and he even gets the last big monologue, but this speech, given by another character, may be the most succinct summation of Linklater's ethos as a filmmaker. He tends to use politics as mainly as background context, but it is their inquisitive nature, their philosophical wondering and wandering, that offers hope for a future.