Terry Gilliam in 'Monty Python and the Holy Grail'
Terry Gilliam (1940 - )
Director/animator
Monty Python's Flying Circus: Episode 1, Whither Canada? (1969) [Nazi Guard]: Laughs himself to death when Michael Palin rapidly recites the world's funniest joke in German, after Terry bursts into the room. (Note: The Pythons played multiple roles in each episode; I will only be listing the specific characters that die.)

Monty Python and the Holy Grail (1975): (1) [Green Knight]: Stabbed through the head when John Cleese throws a sword at him at the end of a fight. (2) [Sir Bors]: Decapitated when the killer rabbit bites through his neck. (3) [Animator]: Dies of a heart attack at his drawing table, causing the animated monster to disappear. (4) [Old Man from Scene 24]: Thrown into the Gorge of Eternal Peril by supernatural forces after Graham Chapman asks a question that Terry can't answer. (Thanks to Katherine and Tommy)

Jabberwocky (1977) [Man with Rock]: Partially eaten by the monster; what's left of his body is shown afterwards as the monster leaves. (Thanks to Tommy)

Monty Python's The Life of Brian (1979): (1) [Crucifee]: Executed by crucifixion; he is shown on the cross singing with the rest of the prisoners as the movie ends. (Thanks to Katherine and Tommy)

Monty Python Live at the Hollywood Bowl (1982): (1) [Flying Minstrel]: Shot in the stomach by John Cleese after Terry finishes a song while suspended in mid-air.

Monty Python's The Meaning of Life (1983): (1) [Walters]: Shot by German soldiers as he tries to set up a table in the trench. (2) [Mr. Brown]: Liver cut out by Graham Chapman during a "live organ transplant." (3) [Howard Katzenberg]: Dies of food poisoning (along with the other guests) from Eric Idle's spoiled salmon mousse; they all collapse and their spirits rise from their bodies after the Grim Reaper (John Cleese) collects them. (Thanks to Katherine and Tommy)
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