6. The Graduate
Tired of being the golden boy for his parents friends, college track star Benjamin Braddock embarks upon an affair with the wife of his father's partner. Benjamin leads a frustrated life and often sees adults in a surreal way, so he hopes to relax and sow his wild oats as suggested by his mistresses husband, but is dismayed to find himself just another tool to ease middle-aged insecurity.
Here's to you, Mrs. Robinson! Seriously though, what high school boy hasn't fantasized about casual sex with a much older woman, be it a neighbour, a teacher, friend's sister, etc.? It was such a well directed movie that the fact that Anne Bancroft and Dustin Hoffman are only six years apart in age (Hoffman was 30, Bancroft was 36) didn't ruin it for me. I don't think the term "cougar" was well-known by 1967, but when I watched it, I found it amusing that Mrs. Robinson tended to wear a lot of clothing with animal prints. This movie is also about the generation gap that existed in the 60s. Elaine and Benjamin are fresh out of university and they are both very different from their parents. The fact that none of the character's first names are identified except for Benjamin, Elaine, and Carl enhances that generation gap image. Benjamin's naivety is also one of the most funny parts of the film, since I think we can all remember when we were that socially awkward (hell, I think I still am!)
I actually watched Dr. Strangelove and The Graduate for the first time ever back-to-back in the same night. It blew my mind.
The Graduate was nominated for seven Oscars including Best Picture, Best Actor, and Best Actress, but only Mike Nichols won for Best Director.
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