5 The Fisher King (1991)
A pre-schmaltz Robin Williams, Jeff Bridges, Mercedes Ruehl and Amanda Plummer (all at the top of their game) star in this bleak yet ultimately uplifting story of people at rock-bottom being saved by love. Bridges is an obnoxious radio shock-jock who unwittingly eggs on a man to commit a shooting spree. Among those killed is the wife of Parry (Williams), who thereafter loses his grip on reality and drifts into homelessness, convinced he is one of the Knights of the Holy Grail. (familiar territory for Gilliam). Bridges seeks to redeem his own shattered life by helping Parry find love with an eccentric woman (Plummer) he fancies. Gilliam’s knack for creating a terror stricken, yet somehow fun environment serves this darkly humorous story extremely well.
4 Fear and Loathing in Las Vegas (1998)
An appropriately bizarre and mind-blowing adaptation of Hunter S, Thompson’s gonzo-lit classic, Fear and Loathing in Las Vegas: A Savage Journey to the Heart of the American Dream, is a film that takes multiple viewings to fully absorb and appreciate. Faithful to the maddening experiences described in its source, and featuring two balls-out, unforgettable performances by Johnny Depp and Benicio Del Toro as two men who slip deeper and deeper into drug fueled madness during their trip to Sin City. Depp’s screamingly funny narration, lifted straight from Thompson’s prose, undercuts the zany, tripped out goings-on that take place before your eyes with a priceless brand of matter-of-factness that’s almost too much to handle. The cinematography, practical effects and intricate set dressing collude to create an experience that’s at once visually arresting and visually disturbing. The film features many hilarious cameos, such as Tobey Maguire as a (logically quite frightened) hitchhiker the duo pick up early in the film, Gary Busey as a lonely highway cop and Christopher Meloni as a prissy hotel clerk. A modern classic.
3 Time Bandits (1981)
If your childhood lacked this film, then your childhood was simply lacking. A dark and lively fantasy/adventure featuring an unsavory crew of time traveling dwarves in possession of an ancient, supernatural map (which as one can imagine is a who’s who of British little people commonly seen in productions of this era) and the young boy who accompanies them after they mistakenly crash his bedroom, this is a film that takes you places, in a fashion only Gilliam could. Sean Connery appears as a brave and benevolent King Agamemnon, as does Ian Holm as an insecure Napoleon, and John Cleese as a classically well-kept Robin Hood (whose merry men are the filthy brutes one would realistically expect) as the boy and his new friends are monitored by Evil himself (Tron’s David Warner), who wants the map for himself. Gilliam co-wrote the script with fellow Python alum Michael Palin, and the troupes signature brand of humor is all over this quite special film.
2 Brazil (1985)
More dystopian future madness from Gilliam, this time rather than decimated by a plague, the world (or at least England) is dominated by a massive, controlling bureaucracy, obsessed with collecting, processing and storing records and files. Jonathan Pryce plays Sam Lowry, a mild-mannered mid-level official in said bureaucracy, who is plagued by some very strange dreams, that lead to the unraveling of his highly ordered world. Gilliam’s satirical vision is a site to behold, from the clunky, awkward, scrapped-together machines that run everything, to the plastic surgery-addicted, garishly attired society matrons (among them being Sam’s mother, played expertly by Katherine Helmond) and majestic dream sequences. Brazil rightly earned Academy nods for its script and art direction.
1 12 Monkeys (1996)
Not only is it one of the most logically airtight time travel tales ever woven (apologies with much love, Back to the Future saga) this twisty, atmospheric sci-fi flick, which may have proved far more conventional in other hands, is Gilliam’s best all-around film. Largely inspired by the 1962 short film La Jetee, Bruce Willis plays a man who travels from a plague-ravaged future to the 1990s in order to prevent an unhinged animal rights extremist (Brad Pitt, in a truly bizarre, brilliant, Oscar nominated performance) from releasing the deadly virus that pretty much ended the world as we know it. With its grim and grimy locales (the future is pure Gilliam, all tubes and plastic smocks), intense performances, jarring portrayal of the mental effects of time travel, and eerie plot twist, 12 Monkey’s will haunt you for days, as will its very memorable theme music.
The Adventures of Baron Munchausen – A grand and arresting film, based on the tall tales told by one of history’s great embellishers, German nobleman Baron Munchausen memorably played by John Neville, and scored many awards an nominations for its sets, makeup, costumes, and effects.
That’s the lowdown on Terry Gilliam’s best work. If you feel like something was left out (and for some reason don’t recognize this was fully intentional), make yourself heard!