6. 12 Monkeys (1995)
The second installment in Gilliam’s second trilogy, the Trilogy of Americana, is based on classic short feature film “La Jetée”, directed by Chris Marker. In “12 Monkeys”, we see a world devastated by a disease where a prisoner travels through time searching for information about this virus that killed most of the earth’s population.
With good performances from Bruce Willis, Madeleine Stowe and Brad Pitt, “12 Monkeys” is among the most acclaimed science fiction films of the 90s. The post-apocalyptic setting of the film and how it travels to other moments of history makes it quite an intriguing tale to watch.
Always remembered as one of Gilliam’s finest works, “12 Monkeys” is definitely a film that must be seen, making it number 6 on our list.
5. Fear and Loathing in Las Vegas (1998)
Few movies capture the essence of the book they’re based on as well as Gilliam’s “Fear and Loathing in Las Vegas”. Based on the novel by the same name written by Hunter S. Thompson, this movie is as visually crazy as the book.
Starring Johnny Depp in one of his best performances and Benicio del Toro, respectively as a journalist and his lawyer, “Fear and Loathing in Las Vegas” is a story about the search for the American dream – and about drugs, of course. It is the last part of Gilliam’s Trilogy of Americana.
Capturing the essence of Thompson’s story and adapting it with great shots, colors and rhythm, “Fear and Loathing in Las Vegas” is not only one of the best films in Gilliam’s career, it is among the greatest book-to-film adaptations of all time.
4. The Adventures of Baron Munchausen (1988)
Following the incredible adventures of an aristocrat from the 18th century, “The Adventures of Baron Munchausen” follows through flashbacks many of the great adventures Munchausen lived, such as travelling to the moon, dancing with Venus, and his many escapes from the Angel of Death.
One of Gilliam’s most remarkable films, the last part of the Trilogy of Imagination is, above all, a story about stories – and particularly how you tell them. This struggle between reality and fantasy, in this place very well-positioned in this character’s glorious past, is used marvelously in this film.
With amazing performances from John Neville, Sarah Polley and Robin Williams, “The Adventures of Baron Munchausen” is definitely among the most outstanding fantasy films made in the 80s, a decade definitely known for that genre. This great story about storytelling with its great setting and impeccable production design makes “The Adventures of Baron Munchausen” number 4 on our list.
3. The Fisher King (1991)
The first part of the Trilogy of Americana, “The Fisher King” follows a radio star who quits his job after a mad listener kills a lot of people in a bar in New York City. Deeply depressed, he meets a homeless man connected to the massacre who is in search of the Holy Grail.
With beautiful performances by Robin Williams and Jeff Bridges, this is one of the best stories in Gilliam’s career. This tale of the improbable friendship between a man searching for his own forgiveness, and a professor that descends into madness after a tragedy. keeps moving audiences 26 years after it was released.
“The Fisher King” is a must-see film that has many beautiful moments and great dialogue written by Richard LaGravenese. It won the Silver Lion at the Venice Film Festival in 1991, tied with “Raise the Red Lantern” by Yimou Zhang and “I Don’t Hear the Guitar Anymore” by Philippe Garrel. The movie also won a Golden Globe for Robin Williams’ performance and the Oscar for Best Actress in a Supporting Role for Mercedes Ruehl.
2. Monty Python and the Holy Grail (1975), co-directed with Terry Jones
Often and rightfully considered one of the best comedies ever made, “Monty Python and the Holy Grail” is the second film to star the group and follows the story of King Arthur and his faithful knights facing some pretty strange obstacles while searching for the Holy Grail, a task given by God.
With great funny moments like the encounter with the Black Knight (“It’s just a flesh wound”) or with the Knights Who Say “Ni”, “Monty Python and the Holy Grail” is the group at their peak.
Although losing its rhythm in very brief moments, “Monty Python and the Holy Grail” is, as aforementioned, among the greatest comedies in film history by one of the most acclaimed comedy groups of all time and, therefore, a must see film.
1. Brazil (1985)
Gilliam’s masterpiece, the second part of the Trilogy of Imagination, follows Sam Lowry, a man who lives in a totalitarian society ruled by bureaucracy. In this place where the state controls everything, he ends up falling in love with a terrorist.
Influenced by George Orwell’s novel “1984”, Gilliam sets lots of dream sequences to contrast with the tough reality and tunes that have influences from “Blade Runner” to Franz Kafka while composing this chaotic story inside this violent environment.
The necessity to escape, and how fantasy plays a great part in it, is an amazing setting to Gilliam’s most brilliant work to date. “Brazil” is definitely a 20th century masterpiece and must be seen by any film fan, making it number 1 on this list.
Author bio: Vítor Guima is a filmmaker, writer and musician from São Paulo, Brazil. Every day he watches a movie, reads a few pages from a book, listens to an album and freaks out with the feeling of not having enough time to see everything. You can follow him on Instagram on @ovitorguima.