Simon & Garfunkel gained prominence on American radio in 1965 with "The Sound of Silence," following their breakup after the failure of their debut album, Wednesday Morning, 3 A.M. (1964). Their subsequent album, Sounds of Silence (1965), was a commercial success, leading to Parsley, Sage, Rosemary and Thyme (1966), which furthered their critical acclaim. At 25, Simon felt he had achieved a significant status in rock while maintaining artistic integrity.

The duo selected William Morris as their booking agency based on a recommendation from Wally Amos, a friend of their producer, Tom Wilson. During the Parsley sessions, they recorded "A Hazy Shade of Winter," which peaked at number 13 on the national charts, and "At the Zoo," released in early 1967, which reached number 16. Simon began work on Bookends, expressing disinterest in singles and experiencing a writing dry spell, leading to no new album for 1967. This lack of productivity concerned Columbia Records executives, prompting chairman Clive Davis to involve producer John Simon to revitalize the duo's output. Distrustful of label executives, Simon and Garfunkel recorded a meeting with Davis, who urged them to increase production, for later amusement.