OK, I'm back with the movie I've seen the most times...
Monty Python and the Holy Grail (1975)
Directors : Terry Gilliam (1940), not using Terry Jones (1942) here
Male Lead : Lots of choices, well, six. Well, actually, since two of the cast were directors and two others are the same age, only three new choices
Female Lead : Carol Cleveland as Zoot/Dingo (1942), If it's allowed, I'll use her best line as my team name
Producer : Michael White (1936)