Like him or not, there’s no denying the distinctive style and energy of a movie directed by Terry Gilliam. The former animator and the lone American member of Monty Python, Gilliam turned his unique take on material and his penchant for very wide-angle and fish-eye lenses into a filmmaking career that’s spanned over 30 years. While he was co-director on Monty Python and the Holy Grail and he directed the short The Crimson Permanent Assurance that began Meaning of Life, for this list of his five best films, I’m going to focus only on the features that he directed solo. He’s a filmmaker I’ve always liked but have recently come down on the side of really loving, even if the films he makes aren’t always my cup of tea. He knows what he wants and will complain if he doesn’t get it. And for God’s sake, will someone just let him make his Don Quixote movie?

5) Time Bandits (1981)
With his first few films, Gilliam was doing his version of fantasy films. In fact, all of his movies have tended to have an air of the fantastical about them, but have gotten steadily more grown-up as he went. For his second feature, Gilliam and his Python cohort Michael Palin wrote a script full of absurd humor and childlike exuberance with the story of a young boy who gets pulled from his bedroom into a world of time traveling thievery with a group of guys who used to work for God. Yep, that’s what it’s about. And they always seem to ruin everything for our young hero, who gets to meet Robin Hood, King Agamemnon, Napoleon and more. Gilliam’s art direction in this is unmatched and incredibly stark, and his sense of camera timing and movement is incredibly assured. He was an animator, after all; dude knows how to get the visuals he wants. I didn’t love this movie the first time I saw it, but over time it’s really grown on me.

4) Fear and Loathing in Las Vegas (1998)
We go from Gilliam’s most family-friendly film to arguably his least. A startling and disturbing visual representation of Hunter S. Thompson’s landmark gonzo memoir, Fear and Loathing is so viscerally evocative that it makes even the straightest-edge person know what a drug-fueled stupor might feel like. Johnny Depp gives one of his best performances as one of his first nutso-bonkers characters. He makes Raoul Duke both wholly despicable and weirdly likable, especially opposite Benicio del Toro’s psychopathic Dr. Gonzo. Gilliam based a lot of his visuals and effects on Ralph Steadman’s famous illustrations and it truly feels like that in live action, especially the creepy-ass lizard sequence.

3) The Adventures of Baron Munchausen (1988)
This is a film that I hadn’t seen until recently but it’s already skyrocketed in my book. Written by Gilliam and his friend and writing partner Charles McKeown, Baron Munchausen combines Gilliam’s love of historical settings with his knack for colorful characters. The titular Baron (John Neville) arrives in a town in an unnamed European town, somewhere sort of Germanic, that’s been ravaged by a war. A traveling theatre troupe is telling some of the Baron’s famous feats on stage and the old man interrupts to say how inaccurate they are and begins telling what really happened. The very young daughter (Sarah Polley) of the theatre owner takes a shine to the old weirdo. Many of the same actors from the play within the movie show up as members of his old crew, including Eric Idle. This is the perfect story for Gilliam’s brand of practical effects, that all look handmade. A theatre troupe putting on a play would have those kind of effects, and are quite impressive in that respect. This is just a joyfully good time watching a movie, and it makes me wish I’d seen it when I was actually a child.

2) 12 Monkeys (1996)
You can’t have better source material for a movie than a Chris Marker film, and Gilliam’s ode to dystopian fatalism is the better for it. Expanding Marker’s La Jetee, which was a short made out of black and white still images in a sequence, David and Janet Peoples’ script is a paranoid fever dream where we’re in the same boat as Cole (Bruce Willis) by never actually knowing if what we’re seeing is real, or if he’s actually traveling in time or just a crazy person. Gilliam makes the future world as dark and bleak as anything he’d ever shot, and the present/past didn’t look much nicer. This represents Gilliam’s other strong suit, which is creating an oppressively terrifying world where our hero is never safe, and by extension neither are we. Sent back in time (or possibly not) by unseen government people, Cole has to try to find the source of, and ultimately stop, the spread of a deadly virus that destroys most of Earth. But, everybody thinks he’s crazy, which is an idea I’m sure Gilliam felt some kinship with. Causal loops are bad news, bears.

1) Brazil (1985)
This is my favorite Terry Gilliam movie simply because I think this is the most Terry Gilliam a movie has ever been. It has everything – dystopian future, fantasy elements, adventure, bleak outlook, wicked sense of humor, and a main character who we side with but don’t necessarily like entirely. This is the movie that nearly blacklisted Gilliam forever following his feud with Universal head Sid Sheinberg when control over the final edit was taken away from him, and the disastrous “Love Conquers All” cut gutted most of what made the movie so special. A film like that deserves to be seen. Jonathan Pryce plays government middle-man paper pusher Sam Lowry who spends his days watching old films and daydreaming about being a winged and armored hero, and dreaming to fall in love with the woman of his dreams, who he actually meets in the form of a mysterious resistance leader. Things as simple as paperwork become of ultimate importance and a simple misprint can lead to a man’s legally-sanctioned murder. Beginning funny but ending very unfunny, the complete cut of this movie is a perfect vision of Gilliam’s world.

Featured Image Copyright Cedric Arnold