While James Cameron recently spent $250 million for the technical wizardry to create a cinematic experience like we’ve never seen before, Terry Gilliam spent about a tenth of that amount on The Imaginarium of Doctor Parnassus and created a world we’d never imagine. Cameron’s plot was compelling but conventional; Gilliam’s was compelling, anything but conventional and eventually frustrating.
The premise is a perfect vehicle for Gilliam’s imagination, which has remained wonderfully bizarre through the years. Christopher Plummer plays Dr. Parnassus, an ancient carny with a magical mirror which transports people inside their own imaginations. He’s pitted against that most notorious of gamblers, the devil, played by Tom Waits, who proves yet again that he’s just as fine an actor as he is a singer or songwriter. A stranger named Tony (Heath Ledger) joins the traveling troupe in Ledger’s final performance before his death, a third of the way through filming. Gilliam’s decision to use Johnny Depp, Jude Law and Colin Ferrel to portray Tony inside the mirror, was a clever work-around, but Plummer and Waits steal this show, anyway.
Their epic struggle, we learn, has been going on for centuries, but the further we get into the film, the more confusing the battle becomes. On one side, we have story and imagination. On the other, temptation? Selfishness? Ease? The rules prohibit black magic but not simple trickery. And as we wait for some sign of redemption, we’re given chaos and confusion in the final act instead.
Like Michel Gondry, Gilliam is adept at creating visual splendor and is capable of creating a masterpiece when the story is there to back it up. For the first half of Imaginarium I had hope that I was witnessing such a masterpiece, which made the last third of the film all the more disappointing. All the lovely threads Gilliam follows never quite weave together.

Maybe that is one of the points of the film. All the threads in life never do weave together in the end.
Loved this movie. I went to see it yesterday because I thought it would be a "good warm-up in trippy-ness" for Alice in Wonderland, which I plan to see as soon as I finish re-reading the book.
I was not disappointed. The first 30 minutes were spent trying to figure out what was going on, but I was captivated, not frustrated. Lily Cole's character (Valentina) was intriguing, and Andrew Garfield (Anton) showed that post-pubescent boys can be just as love-struck and awkward as Michael Cera shows pre-pubescent boys can (Arrested Development, Juno). Christopher Plummer (Dr. Parnassus) had the "lovable old man" charm, but as the back story unfolds and we see his selfishness and foolishness in dealing with the Devil, Cole and Garfield become that much more important in holding our affections.
My favorite aspect of this movie, though, was the variety of actors playing Tony. In The Dark Knight, the Joker is a simple character. Yes, his past is shrouded in mystery, but as we see him, evil, suffering, and chaos are his gods. Tony, on the other hand, is as two-faced as, well, Two-Face. His god is himself, and that breeds complexity. His many faces force us to question how he sees himself, and we are never given an answer.
In light of Tony's many faces, Val and Anton become that much more compelling: they know who they are and aren't ashamed of it. Yes, Anton wants Val and Val wants escape, but they don't hide it.
Complex moral of the story: recognize that life isn't how you always hoped it could be, hope for restoration, but don't sacrifice what is important (needy children, your 16-year-old daughter, etc) for it.
Simple moral of the story: don't make deals with the Devil.