Icon: Simon and Garfunkel

In Order of Importance

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  Bookends by Simon & Garfunkel

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  Although its cover art does little to dissolve self-serious folksinger stereotypes (matching black turtlenecks? Artfully cocked heads?), 1968's Bookends is a stunning collection that includes two of the duo's most heartbreaking songs: Whose stomach doesn't plummet once or twice during "Mrs. Robinson" ("Where have you gone, Joe DiMaggio? A nation turns its lonely eyes to you," Simon implores) or "America" ("'Kathy, I'm lost,' I said, though I knew she was sleeping / I'm empty and aching and I don't know why")? Looking beyond the beauty of its melodies, Bookends is also a brutal examination — pre-blog — of the identity-grasping that almost every 25-year-old endures (Simon was 27 when it was released).

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• 
  Parsley, Sage, Rosemary And Thyme by Simon & Garfunkel Pick

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  Recorded in Nashville in 1966, Parsley, Sage, Rosemary, and Thyme is legendary for its production alone — epic overdubs, swooning arrangements, interwoven vocals and measured instrumentation (the harpsichord on "Scarborough Fair/Canticle," Paul Simon's rearrangement of a British folk ballad, is so well placed it's genuinely chilling — no small feat for a harpsichord). Balancing the studio trickery is "The 59th Street Bridge Song (Feelin' Groovy)," one of the duo's goofiest pieces ("Hello lamppost, what cha' knowing? / I've come to watch your flowers growing /Ain't cha got no rhymes for me? / Doot-in' doo-doo, feelin' groovy").

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• 
  Bridge Over Troubled Water by Simon & Garfunkel

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  The band's fifth and final studio album hints at Paul Simon's future (the whoops and frenzied percussion of "Cecilia" foreshadow the polyrhythms and complex harmonies that eventually come to mark Simon's solo career), but also features Art Garfunkel's professional apex, arguably one of the most-discussed pop vocal performances of all time: his impeccable rendition of "Bridge Over Troubled Water." It also includes "The Boxer," the duo's supposed shakedown of Bob Dylan (Simon contends it's autobiographical). The track — with its booming snare drum blows and finger-picking by famed Nashville session guitarist Fred Carter Jr. — reportedly took over 100 hours to produce.

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• 
  Wednesday Morning, 3 A.M. by Simon & Garfunkel

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  The title of Simon and Garfunkel's debut is also a convenient summary of their guiding emotional aesthetic: mundane, early morning, mid-week melancholy — the most excruciating kind around. Even though it only contains four original songs (mixed in with covers and three traditional folk songs), Simon's dexterity as a lyricist ("The words of the prophets are written on the subway walls / And tenement halls," he observes in "The Sound of Silence") was already obvious. Simon and Garfunkel split shortly after the record was completed (Simon moved to the U.K.), but regrouped when a modified version of "The Sound of Silence" began getting unexpected airplay on U.S. radio (producer Tom Wilson dubbed in electric guitars, bass, and drums — in the spirit of the Byrds — and released it to radio without the duo's supervision). Although Wednesday Morning, 3 A.M. was originally — and, at first, unceremoniously — issued by Columbia in 1964, it was trotted out again in 1966, when it fared much better, given the duo's newfound notoriety.

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• 
  Live From New York City, 1967 by Simon & Garfunkel

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  Like Woody Allen, Lou Reed and thin-crust pizza, Simon and Garfunkel — both natives of Forest Hill, Queens — are inexorably linked to New York City and this show, recorded at Lincoln Center's Philharmonic Hall on January 22, 1967 (it wasn't officially released until 2002), is the first in a string of noteworthy hometown performances. It also captures the duo mid-career (pre-The Graduate, post-"The Sounds of Silence"), before the tension that eventually spurred their breakup seeped into their live performances.

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• 
  The Graduate by Simon & Garfunkel

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  Most of these tracks can be found on other Simon and Garfunkel records, but as a compilation, it's a satisfying, comprehensive introduction to the band, and a compelling argument for single-artist film soundtracks (upon its release in 1968, it dislodged the Beatles' The White Album from its perch atop the Billboard chart). Director Mike Nichols, who reportedly listened to Simon and Garfunkel exclusively while shooting the film, implored Simon for a few original songs; ultimately, a work-in-progress — "Mrs. Robinson" — was adapted for the screen.

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• 
  Sounds Of Silence by Simon & Garfunkel

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  Released in 1966, Sounds of Silence — Simon and Garfunkel's second studio album — is an obvious deviation from the traditional acoustic folk of their debut. Now embracing the folk-rock hybrid inadvertently pioneered for the band by Tom Wilson, the duo folded in a bevy of electric instruments, and although the strength of the songs is undeniable (see "I Am A Rock," "Richard Cory"), folk purists have still derided the pair's move towards a more commercial sound.

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