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Born Yesterday (1950)
Only downside is Ms. Holliday isn't on screen for the whole film.
So, this is one of the funniest movies ever made in Hollywood. I'd rank this one around 6th or 8th in my "funniest movies ever" list.
The scene where Ms. Holliday is keeping time to "Commando Patrol" is one of the funniest/most subtly funny scenes in all of movie history!!