You can easily connect the dots of that plot to Gilliam's take on his own career. "I started at the top of every profession I've ever been in, but I work my way down, though, eventually," he deadpans. In the 30-year "downward" progression since Gilliam's triumph as Monty Python's resident animator, his career has oscillated between success and stumble, though his rise from cutup with cutouts to art film auteur is remarkable in itself. Prior to Python, Gilliam, the lone American in the troupe, had worked as an editor and cartoonist in New York at Harvey Kurtzman's Help! Magazine, where he first hooked up with John Cleese. After moving to the U.K., he got a job writing and animating sketches for a British children's TV show, Do Not Adjust Your Set, which featured future Pythons Michael Palin, Terry Jones and Eric Idle. Gilliam eased into features as a co-director when Python got the funding to do its first film, 1975's Monty Python and the Holy Grail. "Terry Jones and I, who'd both been chafing at the bit during the television series wanting to direct, said, 'Anybody named Terry gets to direct,' " recalls Gilliam with a chuckle.
Although over the years he's developed a bad-boy reputation in Hollywood for costly, snafu-plagued productions, he's achieved critical and box office hits, like Time Bandits, The Fisher King and 12 Monkeys. Other films, like Brazil, The Adventures of Baron Munchausen and Fear and Loathing in Las Vegas, have gone on to become cult classics. There's also the aborted The Man Who Killed Don Quixote, the calamities of which were captured in the documentary Lost in La Mancha. (Gilliam says, however, that he's in the final stages of resecuring the script rights, so the film may be back on track.) What's clear in all his handiwork is that Gilliam doesn't like to make things easy for his viewers. "My films are heightened reality and they get the audience's imagination working," he says. "Even something like Tideland--people say it's taken them days to absorb. I like to create experiences that really stick with the audience. When I make films, for a brief moment I get to create worlds. It's my chance to play God, a pathetic little God," he laughs. "Even within a commercial, I like the idea of creating a world almost to the extent that it exists outside the commercial."
But spots are a decidedly rare outing for the 66-year-old director, who's repped by @radical.media. "I do a commercial every five years, when I get depressed that I'll never make a movie again," he snickers. His last major effort was 2002's "Secret Tournament" for Nike and Wieden + Kennedy/Amsterdam, featuring soccer all-stars in an underground match inside a rusty battle tank. In 1994, he directed another Nike spot in which giant heads of team owners loom over singing baseball champs. Now that he has a bit of downtime, he's available for commercials, but anyone who wants to work with him should be prepared. "I don't like it when somebody's standing in the background, fretting, getting nervous, twitching," Gilliam says of shooting spots. "It makes me fret and twitch. So my approach is, when I'm in doubt I put the creatives on the floor as the director." Or, in the case of 72andSunny's Glenn Cole, who worked on "Secret Tournament" as a CD at Wieden, "he told me to go sit in the corner," Cole recalls, semi-fondly. But he adds, "I'd hire Terry again in a heartbeat, ideally on a project that doesn't have a lot of requirements, where he could run with his impulses. For instance, for a client like Zune, where he can interpret a simple, personal idea and run rampant. If nothing else, 'Secret Tournament' left me wanting to work with him again. He's just too smart, too interesting and too special. Even from sitting in the corner I could see that."
Longtime W+K CD Jim Riswold, who worked with Gilliam on the baseball spot, also believes the strife is worth it. "I count it as one of the highlights of my dislocated life and career that I got to meet and work with Terry," he says. "He's the smartest person I've ever met in my life. We could learn a thing or two from the Gilliams of the world: You will only succeed gloriously if you are willing to fail gloriously."