I tried to give THE GRADUATE another chance recently and still found it despicable. Robin Wood nailed it when he told me, "I would like to run a movie theater so I could show a double bill of THE GRADUATE with THE LAST PICTURE SHOW so that people can see how mean Mike Nichols really is."
The only thing that holds up is the cinematography by Robert Surtees, which is beautiful and inventive, though Nichols overdoes the Antonioni imitations and so on. It is worth noting, however, that Nichols evolved beyond the portrayal of the Anne Bancroft character as a villainous harpie.
Nichols faced and examined misogyny with CARNAL KNOWLEDGE, thanks in large part to a superb script by Jules Feiffer. Another true zinger about THE GRADUATE was offered by Mort Sahl, who noted, "No wonder that kid's screwed up. He's a Jewish kid with Gentile parents."
I always had trouble with Ben because he's such a smug, entitled, self-righteous rich kid with no empathy for anyone else and no sense of what he actually wants to do in life. That could have been the basis for a good satire, but instead he was portrayed as some kind of hero or exemplar of young people at the time, and most of my peers identified with him.
One problem with the film is that Nichols thought of it as taking place around 1963-64, which became his excuse for its weird avoidance of the issue of the war and the draft. That air of unreality contributed to its popularity and makes it seem all the more strange today, since most people at the time of its release (me included) took it as being set in 1967.
Nichols said he had some pushback when he showed it on campuses at the time for that very reason. If THE GRADUATE had made that theme clear and dealt with it, that would have made it better. Shampoo is an example of a film that is a period film set just a few years earlier than its making, which is hard to do.