Produced by Paul Simon, Art Garfunkel and Roy Halee, the album was released on April 3, 1968, in the United States by Columbia Records.

Bookends was considered a breakthrough for the duo, placing them on the same level as artists such as Aretha Franklin, The Beatles, Bob Dylan, and The Rolling Stones at the forefront of the countercultural movement in the 1960s.

Simon & Garfunkel first became prominent on American radio in 1965 with their record "The Sound of Silence", which became a hit during a period in which the duo had broken up due to the failure of their debut album, Wednesday Morning, 3 A.M. (1964).

Simon, then 25, felt he had finally "made it" into an upper echelon of rock and roll, while most importantly retaining artistic integrity ("making him spiritually closer to Bob Dylan than to, say, Bobby Darin", wrote biographer Marc Eliot).

[1] The duo chose William Morris as their booking agency after a recommendation from Wally Amos, a mutual friend through their producer, Tom Wilson.

[1] During the sessions for Parsley, the duo cut "A Hazy Shade of Winter" and decided to release it as a single then, where it peaked at number 13 on the national charts.

[6] Simon was distrustful of "suits" at the label; on one occasion, he and Garfunkel brought a tape recorder into a meeting with Davis, who was giving a "fatherly talk" on speeding up production, in order to laugh at it later.

[1] Leonard Hirshan, a powerful agent at William Morris, negotiated a deal that paid Simon $25,000 (US$219,043 in 2023 dollars[9]) to submit three songs to Nichols and producer Lawrence Turman.

It was just a wonder that you were allowed to do this, that two middle-class kids can sign a contract, rehearse and get their talent into the studio, and then find that the entire distribution network is waiting to put out their products.

[15] He took a bigger role in all aspects of production, and harmonies for which the band was famous gradually disappeared in favor of songs sung solo by each member.

[17] John Simon's work with the duo produced several tracks that ended up on Bookends, such as "Punky's Dilemma", "Save the Life of My Child", and "Overs".

[18] Her observations were reported in the November edition of the magazine: The team's working relationship is built upon listening to each other, asking advice, taking it, building each other's morale.

[22][23] James Bennighof, author of The Words and Music of Paul Simon, finds that "textural elements are variously supported by a churning groove, percussive, and distorted electronic sounds" that complement the song's subject matter, suicide suburban youth.

[24] In "Old Friends", the title generally conveys the introduction or ending of sections through repetition, and the song builds upon a "rather loose formal structure" that at first includes an acoustic guitar and soft mood.

[26] An additional element is introduced midway through the track: an orchestral arrangement conducted by Jimmie Haskell, dominated by strings and xylophone notes.

Horns and other instruments are added when the duo cease singing, creating a turbulence that builds to a single high, sustained note on the strings.

"[15] In "Fakin' It", melodies are occasionally deleted to suit lyrics, but the song generally follows a similar chord structure and melodic outline over a "funky rock beat" that sonically references the Beatles' "Tomorrow Never Knows".

[28][27] "Punky's Dilemma" is breezy and minimal musically, with a soft jazz-style percussion and seemingly improvised guitar lines dominated by major and minor seventh chords.

[32] While concept albums were fairly common among rock groups at this time—such as The Rolling Stones' Their Satanic Majesties Request, The Byrds' Sweetheart of the Rodeo and Iron Butterfly's In-a-Gadda-Da-Vida—Bookends enjoyed massive success with the format not unlike the Beatles nearly one year before.

"[15] Bookends contains many of Paul Simon's major themes, including "youth, alienation, life, love, disillusionment, relationships, old age, and mortality".

According to James Bennighof, the song "deals with individual crises in crowded urban settings, along with references to larger societal forces and at least a hint of some transcendent perspective".

[35] It is a protest song that "creates a cinematic vista that tells of the singer's search for a literal and physical America that seems to have disappeared, along with the country's beauty and ideals".

[29] "Mrs. Robinson" collects wide-ranging images to address social milieu, with a constant reassurance that Jesus loves the eponymous character, God will bless her, and heaven will welcome her.

In January 1968, the duo appeared on a Kraft Music Hall special, Three for Tonight, performing ten songs largely culled from their third album.

[27] Bookends received such heavy orders weeks in advance of its release that Columbia was able to apply for award certification before copies had left the warehouse, a fact that was touted in magazine ads.

[42] Rather than implement Davis' price increase plan, Simon & Garfunkel signed a contract extension with Columbia that guaranteed them a higher royalty rate.

"In just over 29 minutes, Bookends is stunning in its vision of a bewildered America in search of itself", said AllMusic writer Thom Jurek, who gave it five stars out of five.

[50] Pitchfork Media's Stephen M. Deusner called Bookends the moment in which the duo "were settling into themselves, losing their folk revival pretensions and emphasizing quirky production techniques to match their soaring vocals".

[52] "Mrs. Robinson" became the first rock and roll song to win Record of the Year at the 11th Annual Grammy Awards in 1969; it was also afforded the honor of Best Contemporary Pop Performance by a Duo or Group.

[33] Disc jockey and author Pete Fornatale writes that Bookends represents "a once-in-a-career convergence of musical, personal, and societal forces that placed Simon & Garfunkel squarely at the center of the cultural zeitgeist of the sixties".