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Ranked: Terry Gilliam Films From Worst to Best

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The American Python and visionary director gets his canon Ranked.

By David Sterritt, author of Terry Gilliam: Interviews

Terry Gilliam is one of cinema’s great fabulists. After emigrating to England in 1967, disgusted with Vietnam-era American values, he had a lengthy stint as animator-in-residence for Britain’s legendary TV show Monty Python’s Flying Circus, then made the leap to theatrical features in 1974. His breakthrough picture, Time Bandits, celebrated its thirtieth anniversary this week. Gilliam’s movies range from nearly sublime to utterly ridiculous, which makes his body of work perfect for ranking.

11. The Brothers Grimm (2005)

Gilliam had a prolific but not especially successful year in 2005, producing two of his least interesting movies. The Brothers Grimm stars Matt Damon and Heath Ledger as the eponymous fairy-tale collectors, portrayed as con artists whose phony demon-slaying racket turns perilous when they enter a forest that’s actually haunted. Fittingly given the film's title, some blame falls on executive producers Harvey and Bob Weinstein, who feuded with Gilliam throughout the production, delaying the release for almost a year.

10. Tideland (2005)

Gilliam’s unfortunate 2005 continued with this schizofantasy about a heroin addict, his emotionally troubled daughter, a dilapidated farmhouse, and some very weird neighbors. Jeff Bridges is completely at ease in this territory, and the story is classic Gilliam, featuring a child — a child who converses with dolls’ heads, a corpse preserved via taxidermy à la Psycho, a mentally challenged child-man with a stash of explosives in his room. But the imaginative elements end up clogging the story instead of energizing it. So many nightmares, so little time.

9. The Adventures of Baron Munchausen (1988)

Few modern filmmakers claim Georges Méliès as a major influence, but this white elephant of an epic is an overambitious homage to the magic of primitive cinema. It’s hard to beat for sheer spectacle, whether the eighteenth-century hero is surfing the sky on a cannonball or matching wits with the King of the Moon. What's missing is lightness, ease, and humor; they're traded for labored ingenuity and monumental cuteness. Gilliam trimmed bits and pieces throughout the film to achieve the contractually required running time just before release, and he’s always insisted the movie works beautifully in his original cut. If so, it’s a pity the pared-down version is the only surviving one.

8. Jabberwocky (1977)

The title comes from Lewis Carroll, the characters have names like Griselda Fishfinger and King Bruno the Questionable, and the style is Monty Python gone medieval. The dreaded Jabberwock is played by an actor walking backward in a monster suit, and that kind of comic klutziness is inadvertently present in the film’s other elements as well, turning Gilliam's first feature as solo director into a lumbering piece of entertainment and little else. At least Michael Palin, one of the best Python performers, is at the top of his game.

7. The Imaginarium of Doctor Parnassus (2009)

The too-much-ness of the title (thirteen syllables!) signals the tone of the movie: creative, but ultimately more frantic than fulfilling. Christopher Plummer plays the titular magician whose stage opens on a fantastic neverland of imagination, and Tom Waits is terrific as Mr. Nick, a devil who wants to recapture the souls liberated by Parnassus. Heath Ledger’s death during production forced Gilliam to reinvent his character as a protean figure who morphs into Johnny Depp, Jude Law, and Colin Farrell, and the action zigzags accordingly. Gilliam has suffered plenty of bad luck in his career, but Ledger’s untimely departure was a blow worthy of Mr. Nick himself.

6. The Fisher King (1991)

On the skids after a career disaster — one of his monologues sparked a murder-suicide — a radio talk-show host meets a sidewalk schizophrenic whose voices are telling him to steal a trophy (which he thinks is the Holy Grail) from the home of a billionaire he's never met. When it isn't bogged down in romantic subplots, this pitch-dark comedy has great energy and visual imagination. Its view of urban poverty is hardly subtle (hardship wouldn't matter if homeless people had Robin Williams around to make them laugh), but reliable Jeff Bridges is on hand to smooth down some of the movie’s many rough edges.

5. Twelve Monkeys (1995)

In a future society driven underground by a deadly epidemic, a convict travels to the bygone year of 1996, looking for a bizarre animal-rights group that may have that may have unleashed the illness. Gilliam had never seen Chris Marker’s towering 1962 classic La Jetée when he set to work on this feature-length remake, but he manages to update, expand, and Hollywoodize the subject without in any way desecrating the French original. Bruce Willis is excellent as the film’s hero, and Brad Pitt is downright unhinged as the activist who dogs his trail. Gilliam's talent for vivid imagery fills shot after shot with an anarchic energy that's appropriate for the unpredictable story.

4. Monty Python and the Holy Grail (1974)

Codirected by Gilliam and Terry Jones — Terry G. focused on visuals while Terry J. supervised the acting — from a screenplay by all six Monty Python members, Holy Grail is rife with verbal wit and visual richness, and its rhythm is perfect. You’d never guess that Graham Chapman (as King Arthur) was often so drunk he could barely stand (much less remember his lines) or that the unusual depiction of horses — the knights trot along the ground while squires clack coconut shells to make clip-clop sounds — grew out of budget limitations, not divine inspiration. As a collective Python project, the film doesn’t quite equal Life of Brian, directed by Jones five years later, but both pictures are excellent and deservedly revered.

3. Time Bandits (1981)

Finding that his bedroom contains a hole in time, a boy ventures through it and emerges in different historical periods, teaming up with a band of diminutive time-traveling outlaws on the lookout for loot. The screenplay by Gilliam and Michael Palin echoes Snow White and the Seven Dwarfs (1937) and The Wizard of Oz (1939), and also C.S. Lewis’s Chronicles of Narnia novels. The action is boisterous and inventive, with flashes of quintessential Python humor, and the excitement doesn’t let up even when the picture muses about the nature of reality, the problem of evil, and God’s relationship to humanity. Time Bandits is a unique, intelligent, freewheeling, and terrific film, complete with a switcheroo ending that few children’s films would dare to present.

2. Fear and Loathing in Las Vegas (1998)

Hunter S. Thompson’s notorious book bounced around Hollywood for ages before Gilliam got involved; Gilliam promptly threw out the existing script and wrote a new one with Tony Grisoni in the course of a few days. The resulting film captures the energy and essence of Thompson’s deadpan pseudobiography and drug-soaked view of America during Watergate and Vietnam years. Gilliam has never made a darker, crazier, more passionate movie, and his principal players — Johnny Depp as Raoul Duke and Benicio Del Toro as Dr. Gonzo — turn in uncannily lived-in performances. The picture failed at the box office, but has since found a rabid cult following: it’s a bold and brilliant milestone in Gilliam’s career.

1. Brazil (1985)

Imagine a Monty Python version of 1984 and you’ll have a dim idea of what this masterpiece is like. A savagely satirical sci-fi noir that uses a miniscule computer glitch to launch a juggernaut of uproarious calamity, Brazil is the tale of a mild-mannered bureaucrat who dares to buck the system in a future society where conformity reigns. The film’s history is as strange as its plot: worried that the stunningly dark ending would alienate American audiences, Universal Pictures shelved it until Gilliam’s unauthorized private screenings and a major critics’ award forced them to release a somewhat altered edition to American theaters. Gilliam’s vision is the driving force of the movie, which also benefits from Roger Pratt’s retina-bending cinematography and a first-rate cast. Technically, intellectually, and artistically, Brazil is a landmark of fantastic cinema.