Director Mike Nichols had just finished the movie Who's Afraid of Virginia Woolf with Liz Taylor & Richard Burton and was now casting The Graduate. About 200 actors tested for the part of Benjamin Braddock. Described in the book, Benjamin was a tall, blond, Robert-Redford-looking young man.
Nichols said, "I wanted to cast the part as someone who's behind a permanent 8-ball, as we all are starting out in life. I found Dustin Hoffman in a Broadway play, playing the part of a 'transvestite Russian fishwife', believe it or not. To me, he looked like I imagined Benjamin Braddock."
Robert Redford and Nichols were good friends at the time because Nichols had directed Redford in his second Broadway play: Barefoot in the Park. It was Nichols first directing job. Now Redford was very interested in The Graduate.
Playing pool at his home, Redford asked Nichols to cast him as Benjamin Braddock.
"You don't fit the part," Nichols told him.
"Why not?" Redford asked.
"Because you can't play the part of a loser."
"Sure I can," Redford insisted.
"Then let me ask you something. When's the last time you struck out with a girl?"
"What do you mean?"
Nichols laughed. "I rest my case."
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And Nichols using Paul Simon's song in The Graduate was another coup. I remember going to see Who's Afraid of Virginia Woolf in a theater in Atlanta, hearing grumbling by some of the, mostly male, theatergoers that it was in black-and-white. Always hated it when people talk to in the theater over the movie.
Ron