Waking Life (2001)

Shot by Richard Linklater and meticulously rotoscoped under a tight budget, Waking Life centers upon an unnamed protagonist who gradually realizes that he's roving through a seemingly-endless dream world. When not subjecting the viewer to surreal and psychedelic imagery, Waking Life spends most of its running time on a series of conversations and monologues about existentialism, Buddhism, the nature of dreams, death, desire, Philip K. Dick, and metaphysics. Depending upon your perspective and your tolerance for cinematic naval gazing, Waking Life can be profound, pretentious, or a little bit of both. Weird animation and babbling on about abstract philosophical theories is catnip to Ryan, so it was likely only a matter of time before he used Waking Life as a subject for this podcast. He's subjecting Cheryl to this one as cohost (she lands firmly on "a little of both" in the question of whether the film is profound or pretentious). Talking points for this one include several of the film's stated themes, but also the movie's tango-inflected score, the unfortunate Alex Jones cameo, the connection between this movie and better-known Linklater projects like Dazed & Confused, Slacker, and the Before Trilogy, and the qualities of rotoscoped animation (Cheryl, coming from an animation background, often finds the process to be lazy and jarring).