When released as a single in 1968, it hit number one on the Billboard Hot 100 chart in the US, for their second chart-topping hit after "The Sound of Silence". An early version of the song appeared in the motion picture The Graduate (1967) and its subsequent soundtrack, while the complete song debuted on their album Bookends (1968). The song earned the duo a Grammy Award for Record of the Year in 1969. Top session drummer Hal Blaine played on the record, and considers it one of his favorites.
In the film The Graduate, listless recent college graduate Benjamin Braddock has an affair with an older married woman, Mrs. Robinson. The song as it appears in the film is different from the familiar hit single version, as only the chorus of the song appears multiple times throughout the second half of the film. It was only later on that Paul Simon and Art Garfunkel re-recorded the song by employing additional lyrics to form the hit single.
According to a Variety article by Peter Bart in the May 15, 2005 issue, director Mike Nichols had become obsessed with Simon & Garfunkel's music while shooting the film. Larry Turman, his producer, made a deal for Simon to write three new songs for the movie. By the time they were nearly finished editing the film, Simon had only written one new song. Nichols begged him for more but Simon, who was touring constantly, told him he didn't have the time. He did play him a few notes of a new song he had been working on; "It's not for the movie... it's a song about times past — about Mrs. Roosevelt and Joe DiMaggio and stuff." Nichols advised Simon, "It's now about Mrs. Robinson, not Mrs. Roosevelt."