Ranking the 5 Best Songs on ‘Bookends,’ the Penultimate Album by Simon & Garfunkel

After a rerecording of “The Sound of Silence” made them stars, Paul Simon and Art Garfunkel churned out a pair of albums in a hurry in 1966 to capitalize. But they took their time for the follow-up. Bookends, released in 1968, represents Simon’s growing fascination with the recording studio as a means of enhancing his songwriting.

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Bookends is a somewhat uncharacteristic Simon & Garfunkel album with many short pieces, including the spoken-word oddity “Voices of Old People” interspersed among the longer works. But there are undeniable high points, including these five wondrous tracks.

5. “Old Friends”

On the last two Simon & Garfunkel albums, Paul Simon seemed to develop a bit of a sentimental streak about his friendship with Art Garfunkel. Perhaps it’s because he could foresee the fast-approaching time when he’d sever their recording partnership. (Sadly, the friendship would eventually follow suit.) This quiet track, which also touches on the themes about the elderly that pop up elsewhere on the record, imagines a time when the pair would be sitting on park benches reliving their past. It’s a short, but undeniably sweet reflection.

4. “Mrs. Robinson”

We realize that a lot of people would probably have this much-loved song higher, but hear us out. First, it’s kind of jammed into Bookends, breaking up the thematic flow. (The single had already become a major hit by the time the album was released, thanks to The Graduate.) As for its quality, the high point is undoubtedly the chorus, which rises to the occasion with a memorable melody and Simon’s free association about Joe DiMaggio. Simon’s angular acoustic guitar riffs are also fine. The rest of it is a bit twee, with the lyrics in the verses almost skewing to the side of parody.

3. “Fakin’ It”

As mentioned above, Simon, in conjunction with producers John Simon (who eventually had to leave the project due to record company issues) and Roy Halee, was involving the studio more than ever on Bookends, and “Fakin’ It” shows off that ambition. Some of the rhythmic fearlessness that would emerge in the early part of Simon’s solo career can be heard here, while the horns punch in and out in all the right places. The narrator’s frustrations with establishing his own identity lead to thrilling, cathartic refrains, with those vocal harmonies as potent as ever.

2. “Hazy Shade of Winter”

Give credit to The Bangles for identifying that Simon’s acoustic riff on this track would work really well when electrified. Regardless, S&G’s original version still packs a punch even without plugging in. “Hazy Shade of Winter” returns to the album’s overlying theme of the passing years, only this time it does so with more of a jaundiced edge. The narrator expresses disgust and frustration that he has let the ever advancing clock get the better of him: Time, time, time, see what’s become of me. But instead of the song being a slow lament, the duo charge full-speed ahead, as if to try to catch up with the years they’ve lost.

1. “America”

Not only the best song on the album, but certainly in the running for the best ever by this iconic duo. “America” makes a strong case that the quality that unites everyone from all corners of the country is restlessness. For all the sights seen and the gentle joshing between the lovers on their bus trip, the lines that hit the hardest reflect inner life: “Kathy, I’m lost,” I said, though I knew she was sleeping / I’m empty and aching and I don’t know why. Meanwhile, the music, featuring the booming drums of session legend Hal Blaine, conjures all the forbidding majesty of the landscape.

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