With that in mind, a quick rundown of Gilliam's style includes the following: his interest in the relationship between birth and death, youth and old age, and the future and the past; a fantastical, almost childlike fascination with history; dark, absurdist humor; heroes impeded by consumerist vice, generational disquiet, the unstoppable march of time, and bureaucratic despotism; and freedom, real and imagined. You can see my five favorite Terry Gilliam films below.
5. The Brothers Grimm (2005) Aspects of this fantasy comedy are certainly tedious, but there are some inspired set pieces here, and the creative character interplay between Matt Damon and Heath Ledger, playing the Grimms, is Python-esque. The way Gilliam meshes the brothers' autobiographical details with elements of their fables gives the film an intriguing metatextual quality.
4. Brazil (1985) With tremendous wit and detail, Gilliam creates a vivid and entirely plausible postapocalytpic world, but like all great dystopian narratives, the film has more to say about contemporary society than a theoretical future society. The incisive satire keeps the story's more fantastical flourishes grounded, and the deep comic irony, though somewhat gutless and callous in spots, ensures a suitably whimsical mood.
3. Jabberwocky (1977) Maybe the director's weirdest movie, quite a feat considering his filmography as a whole. The film is willfully untethered, a chaotic mishmash of black humor, children's fantasy, medieval folklore, absurdist theater, and Grand Guignol. The film sometimes feels like a Python riff—structurally, it's similar to The Holy Grail and Life of Brian, an episodic collection of set pieces whose effectiveness as narrative depends entirely on how much the viewer is willing to forgive—but Gilliam takes a sure step toward cementing his own unique style.
2. The Fisher King (1991) Gilliam's most conventional film, but also his most human, a contemporary fairy tale whose characters are realistically and coherently motivated and whose feelings and impulses derive from such identifiable emotions as insecurity and self-loathing. Gilliam's visual touch is somewhat repressed, but there are bright, aggressive spurts of aesthetic ingenuity—the image of the Red Knight in Grand Central Station might be his most accomplished sequence.
1. Time Bandits (1981) Ostensibly a children's film, this fantasy adventure was made after Jabberwocky and shares many of its bewilderingly perverse charms, but its chief themes and fixations—the French Revolution, Homeric Greece, the ongoing struggle between good and evil—come with more introspection and earnestness. It's one of the most honest films about being young and having imagination, and Gilliam's commingling of fear and anxiety with fun and adventure creates a kind of emotional maturity that often eludes fantasy directors like Peter Jackson and Steven Spielberg.