Monty Python gang member Gilliam has had a pretty successful career doing pretty much everything. Not a lot of humor outside of Python; his dramatic movies have been better received.
The Adventures of Baron Munchausen: A fantasy m0vie about some guy. I’ve never been a fan of Gilliam’s fantasy worlds (I fell asleep watching Time Bandits) and this is no exception. Interesting casting with Jonathan Pryce, Sting, and Oliver Reed to name a few, but I was never intrigued.
Monty Python and the Holy Grail: Not my favorite Python movie, but it easily has the most iconic scenes and quotable one-liners. Uneven in pacing and continuity, but the good scenes are really funny. A good introduction to British humor.
12 Monkeys: Bruce Willis, a prisoner, must travel back in time to the 90’s to find the cause of a virus that kills five billion people. Trippy time-travel stuff, solid plot, and excellent performances. One of the best of Willis’s career, and probably my favorite performance by Brad Pitt (a mental health patient) as well. Gilliam’s apocalyptic future is visually interesting.
Other Terry Gilliam Movies You May Have Seen
Fear and Loathing in Las Vegas
The Imaginarium of Doctor Parnassus
The Brothers Grimm
The Meaning of Life
The Fisher King