The Graduate (Mike Nichols, 1967) 
Even after all these years of watching films, I had never gotten beyond the first half-hour of The Graduate. After reading Mark Harris's book about the Best Picture Nominated films of 1967, my interest was piqued. This is not a groundbreaking film in terms of aesthetics; Bonnie & Clyde was the film of that year that really ushered in a new brand of filmmaking in Hollywood. That doesn't mean that this film is pedestrian; in fact, I think Nichols direction here is actually pretty good with some nice unique shots and elements. The subject matter of the film is more important in the history of things, in that it seems to have landed perfectly into the generational gap of the late 60s. This was and still is a picture for young people, that speaks to the alienation and bewilderment of entering the "real world." It's acutely appealing to me in, seeing how I come from banal, comfortable, middle-class suburbia, in the way Nichols is skewering the privileged culture of Southern California, and by its outgrowth, the mindless suburbs. Benjamin is bored, and perhaps the affair with Mrs. Robinson will bring him some excitement. More than anything, The Graduate hit the public at just the right time, but in fact, the persona of Ben and what he does aren't that different still today. Young people today are still dealing with the issue of what or whom will speak for them, to voice the worries and grievances that they have. It just so happens a film can do that fairly articulately.
As for more about the film itself, what works best is the deadpan delivery of the entire film. The humor of the film is subtle and dry yet it works because it works with the characters well. Dustin Hoffman as Ben sells the role because he lets the more absurd moments overwhelm and confuse him. Most of the talk of this film centers on the affair with Mrs. Robinson but that's really only half the film. Personally, I enjoyed the second half of the film much more, with Ben's dogged pursuit of the Robinson's daughter Elaine. Now that Ben has found some goal to attain, it makes you root for him to get it. There's something between Ben and Elaine (played by Katherine Ross) that's appealing to me even though I can't quite figure out exactly what. Of course the ending has been appropriated quite well into popular culture, and all this time its greatest attribute is overlooked. Yes, Benjamin gets the girl but Nichols does something remarkable for the time and leaves the ending open. We're left with Ben and Elaine on the bus, their elation slowly turning to 'Now what?' terror and that's it. No tidy resolutions, no real happy endings. These two still don't know where their lives will be headed and that's perfectly fine, not having to know. This, and the rest of the film, handled so well by Nichols, a clever screenplay by Buck Henry and the performances quite rightly make The Graduate a landmark film for ushering a new era.
Side note: another wide known element of the film that goes above and beyond the film is the music of Simon & Garfunkel. The most ironic element of the whole thing is that 'Mrs. Robinson' wasn't even finished when the film was released and only two lines of it (besides the instrumental parts) were used in the film. I happen to think Simon & Garfunkel are the one of the most underrated groups in rock & roll history. I know they sold millions of records and have some great songs but they never seem to have much respect or influence nowadays. They seem to be largely forgotten by my generation and that's a shame.