Terry Gilliam's Best Movies Ranked – MovieWeb

Monty Python member Terry Gilliam has established himself as one of the most vibrant, imaginative, and surreal directors of all time.
Some directors spend their careers largely occupying one genre or another, some however manage to avoid being pigeonholed and create a diverse and eclectic body of work in the process. Throughout his career, Terry Gilliam has crafted films that are sometimes comical, scary, fantastical, and sometimes a mix of all these elements combined. Gilliam rose to prominence initially as a member of the Monty Python collective before venturing into his own feature length films.
His profile increased with films such as Time Bandits, Brazil, and 12 Monkeys, among others. Gilliam has long been considered to be one of the most influential and dynamic filmmakers of our time, and his body of work more than represents his tremendous range. With more than a few classics to his name, Gilliam has plenty of popular films, and we've decided to rank his finest achievements. While these are all excellent (as is much of his work, like Tideland and The Imaginarium of Dr. Parnassus), read on to see which Gilliam film comes out on top.
Long labeled as an unfilmable novel and passed up by several directors, an adaption of Hunter S. Thompson's surreal and twisted commentary on America finally found its way to the big screen thanks to Gilliam in 1998. With its debauchery, lurid visuals, and kinetic pace, the subject of Fear and Loathing In Las Vegas was ideal for Gilliam's vibrant and genre-averse style. He depicts Las Vegas as an enticing yet nightmarish funhouse and films Johnny Depp and Benicio Del Toro's antics with a freewheeling glee and energy.
What truly allows Fear and Loathing In Las Vegas to transcend itself is how Gilliam manages to find his own voice while still faithfully honoring Thompson's darkly comic yet insightful perspectives. Several sequences from the novel are translated to the screen with gusto and innovation, and Gilliam doesn't shy away from the novel's more uncompromising material.
Upon release, Fear and loathing In Las Vegas wasn't well-received by critics and didn't quite perform at the box office as expected. Time has been kind to the film, however, and many have praised its faithfulness along with its imaginative visuals, absurd humor, and go-for-broke performances by Depp and Del Toro. Fear and Loathing In Las Vegas has since become a fan favorite and widely regarded in Gilliam's filmography, and is considered one of the best cult classics of the 90's.
One of his earliest films, Time Bandits sets the foundation for many of the trademarks Gilliam would explore throughout his career. As a film, Time Bandits may not be his most accomplished, but it's certainly one of his most purely enjoyable and is full of delightful visuals, sprinted performances, and Gilliam's signature absurdity in full effect. Time Bandits is a consistently entertaining romp and utilizes its concept for some truly inventive and hilarious material, managing to keep it all tightly paced and cohesive throughout. Elements of Gilliam's time with Monty Python are included here, but thankfully his own unique voice is present in many of the film's touches and influences, especially its incredibly dark ending.
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Time Bandits was met with a warm reception and over time has endured a positive reputation by Gilliam fans. As a film, it signaled the beginning of a promising career and showcased Gilliam's potential and emerging vision. While following films may have improved or exceeded upon it, Time Bandits remains an engaging and exciting showcase for Gilliam as a storyteller and is still fondly remembered 40 years since its release. Plus it has a delightful Sean Connery performance.
Despite a career full of imaginative and surreal experiences, one of the boldest films in Gilliam's career is one of his most human. The Fisher King starring the late great Robin Williams and Jeff Bridges is a heartfelt, harrowing, and ultimately poignant exploration of grief, loss, friendship, and the devastating effects of schizophrenia. The film does contain elements of Gilliam's surreal visuals and typical combination of wacky fantasy with melancholic despair, but also emphasizes character in an understated manner and contains arguably Jeff Bridge's best performance and one of William's most moving and affecting turns as well.
While based on Arthurian legend, Gilliam also grounds the film in genuine realism and allows the characterizations to remain front and center, while maintaining his dynamic storytelling techniques as well. Throughout The Fisher King, Gilliam delves into fantasy, dark comedy, and drama, and while a lesser film with so much going on may appear uneven, in his hands it allows for a truly original and unique experience.
The Fisher King received strong critical attention, particularly for Gilliam's mature storytelling and the strong performances from Williams and Bridges, along with a show-stealing turn by Mercedes Raul (who won an Oscar for the film). In Gilliam's filmography, many consider The Fisher King one of his most underrated yet effective films and some even consider it his best along with telling an affecting tale of mental illness.
Time travel films are a dime a dozen these days, but leave it up to Terry Gilliam to turn the subgenre on its head. 12 Monkeys stars Bruce Willis, Brad Pitt, and Madeline Stowe, and involves Willis' character traveling through time to prevent a plague from wiping out more than half the population. The film takes on an unorthodox approach to time travel as it cuts back between multiple timelines, but thankfully Gilliam creates a gothic yet commanding atmosphere in this update of the great French New Wave short film La Jetee.
Related: These Are Some of the Best Movies About Time Travel
The film is filled to the brim with stunning visuals, suspense and plenty of surreal yet engaging trademarks that keep 12 Monkeys constantly engrossing. The film is also noteworthy for how Gilliam manages to juggle the moving bits while also allowing us to remain invested in the characters. Bruce Willis gives a restrained yet powerful performance and his relationship with Madeline Stowe's character adds depth and pathos; Pitt memorably steals every scene he's in with his over-the-top wackiness. As a cinematic experience, 12 Monkeys is exhilarating, surreal, and surprisingly human, and demonstrates Gilliam's ability to be accessible and artful at the same time.
Upon release, 12 Monkeys was received favorably and was also a commercial success as well. The film inspired a television series of the same name and is widely regarded as one of the best sci-fi films of all time. Overall, 12 Monkeys stands as a triumph for Gilliam and still resonates today.
In a career full of triumphs, Brazil is very much Terry Gilliam's magnum opus. Based loosely off of George Orwell's 1984, the film is a dystopian dark comedy starring Johnathan Pryce as mild-mannered Saw Lowry, whose inadvertent bureaucratic mix-up results in him getting involved in a conspiracy beyond what he could've imagined. Like much of Gilliam's output, the film is filled with quirky and memorable visuals, absurd humor, inventive set pieces, and an exuberant yet haunting tone.
Brazil is chillingly relevant to today's world and Gilliam explores themes of consumerism, bureaucracy, and government control but with his trademark humor and wit present. Brazil also combines genres with elements of fantasy, satire, and sci-fi blending together to form a truly singular experience. Brazil has been considered a landmark for the genre and is commonly regarded as one of the best sci-fi films of all time. While Gilliam has made many films in his time, none have quite achieved the level of artistry he brings here. For that reason, Brazil remains his undisputed masterpiece and is still considered highly influential today.

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