The music (and harmony vocals) of Music/SimonAndGarfunkel is often considered to be so hauntingly beautiful, much of their output can really [[TearJerker move one to tears.]]
* "Seven o'Clock News/Silent Night". There's just something in the juxtaposition of the calm and peaceful melody and all the violence in the news report.
* Just stop and really pay attention the next time you hear "The Sound of Silence".
** Even better is the [[http://www.youtube.com/watch?v=m5xVN2mvrq0 original version]].
* "Music/BridgeOverTroubledWater" can absolutely kill some people ([[BrownNote not literally]]), as do the beautiful cover versions by Eva Cassidy and Roberta Flack.
* "Scarborough Fair/Canticle" becomes really depressing when you listen to the lyrics and realize what it actually says. Sarah Brightman's version is particularly haunting.
* "Old Friends/Bookends" can bring a tear to many a person's eye -- and, as time goes on and he keeps getting older, it just gets sadder and sadder.
-->Preserve your memories,\\
they're all that's left you.
* "He Was My Brother", made worse by the fact that it's based on a true story.
* "The Boxer".
* "For Emily, Whenever I May Find Her", especially the version found in their 1972 ''Greatest Hits'' album.
* "The Sun Is Burning".
* "Sparrow." My God, "Sparrow."
* "April Come She Will"
* "My Little Town"
* Their version of Daniel Robles "El Condor Pasa".
* "The Only Living Boy in New York," another autobiographical song.
* Their cover of Jackson C. Frank's "Blues Run the Game" manages to out-sad the original, which is no mean feat.
* Not to mention Garfunkel's solo tune "Bright Eyes", from the ''WatershipDown'' soundtrack.
* The last verse of "A Most Peculiar Man":
-->He died last Saturday
--> He [[DrivenToSuicide turned on the gas and went to sleep]]
-->With the windows closed, so he'd never wake up
-->to a silent world in his tiny room
-->And Mrs Riordon says he has a brother somewhere, who should be notified soon
-->And all the people said
-->"What a shame that he's dead, but
-->Wasn't he a most peculiar man?
* "I am a Rock"
-->Don't talk of love
-->Well, I've heard the word before
-->It's sleeping in my memory
-->I won't disturb the slumber of the feelings that have died
-->If I'd never loved I never would have cried
-->I am a rock
-->I am an island.
-->"Kathy, I'm lost," I said,\\
Though I knew she was sleeping.\\
I'm empty and aching and I don't know why.
* [[https://www.youtube.com/watch?v=dwqwAy85CgY "Richard Cory,"]] where the narrator still desperately wants to be the rich titular character [[spoiler: even after Richard Cory kills himself.]]
-->He freely gave to charity, he had the common touch,
-->And they were grateful for his patronage and thanked him very much,
-->So my mind was filled with wonder when the evening headlines read:
-->[[spoiler:"Richard Cory went home last night and [[MoodWhiplash put a bullet through his head."]]]]
-->But I work in his factory
-->And I curse the life I'm living
-->And I curse my poverty
-->And I wish that I could be,
-->Oh, I wish that I could be,
-->Oh, I wish that I could be