The music of Simon & Garfunkel was a perfect fit for the 1967 film The Graduate, the tale of young, alienated Benjamin Braddock (Dustin Hoffman) and his search to find meaning in his life. Director Mike Nichols propelled the story with songs by the folk-rock duo and jazzy instrumentals by composer Dave Grusin. Released on Jan. 21, 1968, the film's soundtrack reached No. 1 on the Billboard albums chart.

The film also stars Anne Bancroft as Mrs. Robinson, who seduces Braddock and later attempts to break up the love affair between him and her daughter Elaine (Katharine Ross). Nichols, who died in 2014, was surprised that "The Sound of Silence," performed by Paul Simon and Art Garfunkel, meshed so well with the film's narrative.

"I’d been listening to their album every morning in the shower before I’d go to work," Nichols explained in TimeOut, "and then one morning it just hit me: 'Schmuck! This is your soundtrack!' [Film editor] Sam O’Steen worked on weekends, so the next Saturday I brought the track over and it was like, Holy s---, this fits exactly and it’s twice as powerful! It’s one of those miraculous moments you get when you’re making a movie, where everything somehow comes together. It’s better than sex. [Pause] Okay, maybe not better, but it’s indescribably fantastic."

Two versions of "The Sound of Silence" were used in The Graduate. The classic song first appeared on the duo's debut album, Wednesday Morning, 3 AM. Producer Tom Wilson overdubbed drums and an electric backing track to the song and released it as a single, which reached No. 1 on the Billboard Hot 100 in 1966. Along with the single, a beautiful acoustic version was recorded for the film.

"April Come She Will" came from Simon & Garfunkel's second studio album, Sounds of Silence. The song was first heard on Simon's solo 1965 LP The Paul Simon Songbook, a collection recorded in England in 1965 but not released widely in the U.S. until 1981.

"Scarborough Fair," a traditional ballad about a centuries-old British trade fair, was combined by Simon with his own "Canticle" to create the medley that appeared on the pair's third studio album, Parsley, Sage, Rosemary and Thyme.

An alternate version of "The Big Bright Green Pleasure Machine," also from Parsley, Sage, appears on the soundtrack. It is only briefly heard in the film blaring from a car radio at a drive-in.

The one new Simon & Garfunkel tune on the soundtrack – which helped increase the LP's sales – was "Mrs. Robinson." Contrary to popular beliefs, the hit version, which was released on 1968's Bookends, did not appear in the film. The song hadn't been completed in time.

Garfunkel explained in Forbes that Nichols had commissioned four songs from the duo but they'd only delivered three as filming came to an end. Nichols asked Simon what else he had to offer.

"Paul didn’t have anything," said Garfunkel. "So Mike was living with 'April Come She Will,' 'Sound of Silence' and 'Scarborough Fair' as placeholders, learning to love them just as they were in their places. So he told Paul to give him one song for when Dustin is racing down the west coast to break up the impending marriage of his girlfriend, Elaine. It needed to be up-tempo. Paul had the rhythm, but not the song.

"And there, in the sound stage, I said to Mike, 'You know, Paul is working on a song called 'Mrs. Roosevelt.'' Mike said, 'Do you know how right that could be if we just changed the name – the syllables are perfect?' So Paul sung, 'So here’s to you, Mrs. Roosevelt,' and I started harmonizing. When I harmonize with Paul, it falls into place – the history of Simon & Garfunkel.

"So Mike heard the duet, bought the whole idea, but of using Mrs. Robinson instead of Mrs. Roosevelt. There was no verse yet, so in the movie you hear: 'doo doo doo doo doo doo doo doo doo doo doo doo doo doo' – that’s called a song not written yet [laughs] – only the chorus was there."

And even with the chorus Simon didn't have it finished. In the film, they sing, "And here's to you, Mrs. Robinson / Jesus loves you more than you would know / Whoa whoa whoa / Stand up tall, Mrs. Robinson / God in heaven smiles on those who pray / Hey hey hey." But by the time the song was released, the second half was changed to "God bless you please, Mrs. Robinson / Heaven holds a place for those who pray / Hey hey hey."