Originally, Paul Simon had written a song referencing "Mrs. Roosevelt"—meaning Eleanor Roosevelt. But, for The Graduate's soundtrack, he changed the words to "Mrs. Robinson," altering the meaning and creating a classic. (Source)

Mike Nichols described explaining to his friend, Robert Redford, that he couldn't play the role of Benjamin Braddock: "I said, 'You can't play it. You can never play a loser.' And Redford said, 'What do you mean? Of course I can play a loser.' And I said, 'O.K., have you ever struck out with a girl?' and he said, 'What do you mean?' And he wasn't joking." (Source)

Richard Dreyfuss (Jaws, Stand by Me, Close Encounters, What About Bob?) and Mike Farrell (B.J. Hunnicut on the TV show M.A.S.H.) had their film debuts in The Graduate. (Source)

Dustin Hoffman never thought he would get the role of Benjamin because he didn't look the part. MAD magazine did a parody of the film in which Benjamin asked his parents why he was Jewish and they weren't. When Mike Nichols saw the parody, he realized that he probably cast Hoffman for unconscious personal reasons. As an immigrant Jew who fled Nazi Germany, he said he often felt like an outsider himself in the WASP society. (Source)

Hoffman had signed to play a role in Mel Brooks' The Producers but got a call from Mike Nichols about auditioning for The Graduate. Brooks (who was married to Anne Bancroft) knew something about the novel and film and let Hoffman audition because he was certain he was too nebbish and ethnic to get the part of Benjamin. (Source)

Anne Bancroft (Mrs. Robinson) was only 6 years older than Dustin Hoffman and 8 years older than her onscreen daughter Elaine (Katharine Ross). It's called acting. And makeup. (Source)