I'm referring to the roles they played, not the actors themselves. And frankly, I don't particularly care for most of Monty Python's work, nor had I ever heard of Milton Berle before now. What do you expect of someone born in 1988?
And frankly, I'm rather interested in whether or not you think that the events depicted in the Rudy/Trump video will be used against him at a later date. And the "Reagan with the Monkey" won't fly; the average Joe would look at Reagan feeding milk to a monkey and chuckle (or, if you're the average Jane, go "Awww, how cute.").
Now imagine the reaction of the same average Joe/Jane if they saw Rudy Giuliani, in drag, getting his "breasts" fondled. By Donald TRUMP of all people.
Well, rational people will realize it for what it is, comedy.
Irrational people will foam at the mouth over it and somehow say that it condones cross dressing and homosexuality. But irrational people are nuts anyway, and the only time anyone pays attention to them is when they are laughing at them.