The wonderfully weird world of Terry Gilliam is one that any actor would be lucky to join. The former Monty Python cast member steadily became one of Hollywood’s hottest directors with his delightfully absurd films within the science fiction and fantasy genres.

Gilliam is certainly well known for his ability to create dynamic visuals, but that doesn’t mean that he doesn’t need great performances. There’s a deep humanism to his work, and it necessitates some truly excellent performances to bring his characters to life. Here are the ten best performances in Terry Gilliam films, ranked.

Matt Damon

‘The Brothers Grimm’ (2005)

Gilliam’s dark fantasy adventure The Brothers Grimm took a slightly different approach to the fairy tale genre. Matt Damon and Heath Ledger star as the titular heroes, who work as con artists that convince medieval citizens that they actually have magical powers. The pair of miscreants run into trouble when they encounter a real source of dark magic.

Damon is underrated for his talents as a comedian; he’s got a great sense of physical humor to him that works perfectly within Gilliam’s signature idiosyncratic style. Damon’s role in The Brothers Grimm essentially feels like what would happen if his Ocean’s Eleven character was placed in the 19th century.

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Sean Connery

‘Time Bandits’ (1981)

Time Bandits is a lot more family friendly than the majority of Gilliam’s films. While the British comedian is known for his use of crass language, graphic violence, and explicit sexual content, Time Bandits plays out like a more typical family fantasy adventure. The film creates humor for a younger audience by poking fun at various iconic figures from history and mythology.

Among the most amusing scenes in the film is a sequence in Ancient Rome that depicts figures from Greek mythology; Sean Connery steals the film with his uproarious performance as the Trojan War’s King Agamemnon.

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Benicio del Toro

‘Fear and Loathing In Las Vegas’ (1998)

Fear and Loathing in Las Vegas is either the most brilliant or most grating film that Gilliam has ever made, depending on who you ask. The adaptation of Hunter S. Thompson’s autobiography has a darkly hilarious absurdity to its avante garde style that can get fairly overwhelming for anyone that doesn’t appreciate a bit of surreality.

Even those that don’t enjoy this particular black comedy can appreciate the brilliance of the great Benicio del Toro, whose performance as Raoul Duke’s (Johnny Depp) best friend Dr. Gonzo is so bonkers that he manages to make Depp look like the straight man.

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Heath Ledger

‘The Imaginarium Of Doctor Parnassus’ (2009)

Although The Dark Knight was the last film he officially completed, Ledger gave his last screen performance in Gilliam’s bizarre 2009 fantasy epic The Imaginarium Of Doctor Parnassus. It’s tough to watch Ledger considering that it’s not a complete performance, but in many ways the film feels like a perfect swan song.

Tony Shepard is a dreamer who is only limited by his imagination; he feels like an endowment of everything that Ledger meant to the industry. Shepard’s ability to transform allowed Johnny Depp, Jude Law, and Colin Farrell to play different versions of the character.

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Jonathan Pryce

‘The Man Who Killed Don Quixote’ (2019)

The Man Who Killed Don Quixote took Gilliam a lifetime to make, as he was beset with production issues from the beginning of the film’s planned production. Gilliam was so overwhelmed with delays to the film’s completion that it inspired the documentary Lost in La Mancha, which was released over a decade before The Man Who Killed Don Quixote actually hit theaters.

The film centers on a struggling film director (Adam Driver) who is dispatched on a strange adventure when his former actor (Jonathan Pryce) convinces himself that he is actually the famed knight-errant Don Quixote.

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Robert De Niro

‘Brazil’ (1985)

Brazil is Gilliam’s most acclaimed film to date, and perhaps his weirdest (which is no small statement). The science fiction thriller explores a striking version of the world where consumerism, capitalistic greed, and corporate synergy have turned the world into a cruel, impersonal cityscape.

The film centers on the lowly office worker Sam (Jonathan Pryce), who is visited by the revolutionary leader Harry Tuttle (Robert De Niro). De Niro is known for getting over-the-top in his genre roles, but the absurdity that he brings to the role is actually perfect for Brazil’s surrealist themes.

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Robin Williams

‘The Fisher King’ (1991)

Although Robin Williams had given dramatic performances previously in Good Morning, Vietnam and Dead Poets Society, he was at his most heartbreaking in Gilliam’s 1991 dramedy The Fisher King. Williams stars as a crazed homeless man who is brought out of his isolation by a greedy DJ (Jeff Bridges) who has a major change of heart.

Against all odds, the two men become great friends and discover they have a lot to learn about each other after their adventures. Williams received an Academy Award nomination for Best Actor for his performance.

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Eric Idle

‘Monty Python and the Holy Grail’ (1975)

Monty Python and the Holy Grail is still the best film that the British comedy group ever made together. It’s also a far more enjoyable film than the majority of the “serious” films made about Arthurian legends, like Antoine Fuqua’s King Artuhur and Guy Ritchie’s King Arthur: Legend of the Sword.

Gilliam made fun of clichés within the genre by showing the story of Sir Robin (Eric Idle), the completely incompetent, lesser known member of the round table. Sir Robins’ minstrels follow him, singing songs about his great foolery and cowardice.

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Graham Chapman

‘Life of Brian’ (1979)

There aren’t a lot of great “Easter movies” out there outside of typical religious epics like The Ten Commandments or Ben-Hur, but Monty Python’s 1979 comedy Life of Brian might be able to scratch the same itch. Although it was directed by Terry Jones, Gilliam did significant work on the screenplay.

Graham Chapman plays the titular character Brian, whose life within Ancient Rome happens to parallel the experiences of Jesus of Nazareth. During the film’s final moments, Chapman sings the now iconic Monty Python song “Always Look On The Bright Side Of Life.”

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Brad Pitt

‘12 Monkeys’ (1995)

It is often said that Brad Pitt is a character actor in a leading man’s body; despite his good looks, Pitt is capable of playing much more than just heartthrobs. Pitt delivered his weirdest performance ever as the crazed social activist Jeffrey Goines in Gilliam’s 1995 science fiction mystery 12 Monkeys.

It’s rare that an actor can play a character with mental issues with such realism, but Pitt was able to make Jeffrey’s condition feel authentic to the absurdity of Gilliam’s world. Pitt received an Academy Award nomination for Best Supporting Actor for his performance.

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KEEP READING: ’12 Monkeys’ Review: Terry Gilliam’s Sci-Fi Classic Is an Exploration of Insanity