That's nice. I know why you've no rep power. Someone with either 4 or more must have negative rep'd you. Mick's dad told me that's the way it works.
The Parole Officer. Adore that film, Steve Coogan at his brilliant best. Out of those mentioned, probably have to be Naked Gun, I loved Nielsen in those and the Airplane films.
None of the Katherine Hepburn comedies make the list, no Chaplin, nor for that matter any foreign films eg. http://www.imdb.com/title/tt0108500/ so I guess it'll have to be Duck Soup.
Had to choose between Big Lebowski, Life of Brian, Duck Soup and Naked Gun. Chose Duck Soup purely because of childhood memories.
Take out The Great Dictator and Chaplin did nothing of merit that wasn't a short film, but The Great Dictator is a far better political satire than either Duck Soup or Dr Strangelove (or ANY other film) even if many think it less funny.