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
* "The Dangling Conversation" and "Overs" are painful somgs about one partner knowing his relationship has run its course, but has no idea how to end it, and is willing to stay in a loveless relationship out of habit.