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. Also doubles as NightmareFuel.
* Just stop and really pay attention the next time you hear "The Sound of Silence". The lyrics focus on humanity's inability to communicate, and the singer's doomed attempt to break through the barriers everyone around him has put up. Even better is the [[http://www.youtube.com/watch?v=m5xVN2mvrq0 original version]] without the electric instruments.
* "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. On the one hand, there's "Scarborough Fair", about the impossible tasks the singer sets his "true love" (omitting the verses where she sets him similarly impossible tasks), and on the other, there's "Canticle", about the mindlessness of war and the death of innocence it brings. 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 Simon and Garfunkel keep 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.
%%* "For Emily, Whenever I May Find Her", especially the version found in their 1972 ''Greatest Hits'' album.
%%* "The Boxer".
%%* "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.
%%* Garfunkel's solo tune "Bright Eyes", from the ''WesternAnimation/WatershipDown'' soundtrack.
%%Song titles on their own are not proper examples. Do not uncomment the above examples without expanding them to explain why they are sad.
* Their cover of Jackson C. Frank's "Blues Run the Game" manages to out-sad the original, which is no mean feat.
* The last verse of "A Most Peculiar Man". As if hearing about the title character having no friends - his neighbours shunned him for being unfriendly and, worse, different to them - isn't bad enough, he is hurting so much below his surface anger that he finally decides he can't take it anymore, and it becomes clear that no-one will truly miss him once he's gone:
-->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". As happy as the singer claims to be living in complete isolation from other people, the reasons for this choice - not wanting to be hurt again as he has been in the past when his friendships and romances have gone sour - add a solemn edge to the song.
-->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.
* "America" sees two lost souls making their way by bus from Pittsburgh to New York, with no idea where they're going next:
-->"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 songs 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.
* "The Only Living Boy in New York" is similarly sad, as it's about a deteriorating friendship that neither friend can keep.