How many movies have Andrew MacLachlan and Terry Gilliam collaborated on?

They have worked on 4 movies together! Their first movie together was Life of Brian (1979) and was their highest rated movie together. They have not worked together since The Adventures of Baron Munchausen (1988). They are most known for their comedy films together.

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Colonel
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Irritating Singer Inside Fish (uncredited)
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Fireman #2
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Another Official Stoners Helper / Giggling Guard
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Man Even Further Forward / Revolutionary / Jailer / Blood and Thunder Prophet / Frank / Audience Member / Crucifee
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Animation