I am a practicing attorney who writes about everything from pop culture to law.
1. "Mother" by Pink Floyd
Pink Floyd's album, The Wall, is one of the best albums of all time. It's probably my favorite album of all time, too. The movie, while very strange in many ways, was really kind of cool with the visuals and the art.
"Mother" is an interesting song. It's somber, but because of its neutral tone you have to dig a little deeper to sense the level of sadness it contains. "Mother will she tear your little boy apart? Ooooh ma, mother will she break my heart"
2. "The Trial" by Pink Floyd
"The Trial" appears towards the end of disc two of The Wall. Perhaps the majority of the album (and the album's name) is about a secret life of psychosis, inner turmoil and clandestine torment behind the scenes (or, more aptly, behind The Wall), and "The Trial" is in large part about that wall being torn down. "I sentence you to be exposed before your peers!" is a line that best summarizes this one.
3. "Goodbye Cruel World" by Pink Floyd
This is the penultimate track on disc two of Pink Floyd's epic The Wall. "Goodbye Cruel World" is unique in that it has a seemingly positive tone whereas the words expressed couldn't be more despairing. Perhaps it's because in his view (and that of many people inflicted with depression, chronic or isolated), contemplating saying goodbye to this deranged and maniacally cruel world engenders a deep sense of relaxation and relief.
4. "The Postwar Dream" by Pink Floyd
"Should we shout? Should we scream? What happened, to, the postwar dream? Oh Maggie, Maggie what did we do?"
This whole song is sad. The singer somehow blaming himself for his father's death because he watched too much TV, mentioning that it can't be much fun for Japan with all their kids committing suicide (a reference to Kamikaze pilots and a culture that favors willingly dying in battle with no chance of achieving any objective in lieu of surrendering).
5. "Jesus Don't Want Me for a Sunbeam (Unplugged)" by Nirvana
The year was 1993. Not only did MTV predominantly play music videos rather than trashy "reality" television, but around that time, they commenced a periodic series of acoustic performances called "MTV Unplugged" which saw some of the biggest names in music performing, for a lack of a better description, in an "unplugged" manner.
On November 18, 1993, Nirvana played an unplugged show at Sony Music Studios in New York City. It was broadcast far and wide, and it is considered by most familiar with the series to be one of the greatest live performances ever aired on television.
This song, as is made clear from the title itself, is largely about having a pitifully low level of self-worth.
6. "When the Man Comes Around" by Johnny Cash
The inclusion of this entry on my list may be largely, if not entirely, attributed to my association of it with the final scene of HBO's Generation Kill.
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In that context, my view of this scene (see the video linked below) is that it's really nostalgic and sad at the same time as the disillusioned soldiers look back on their time in Iraq.
7. "Bridge Over Troubled Water" by Simon and Garfunkel
To some, it may not make all that much sense that this song is on this list, given that the song is about someone being there for another person when they're at a low-point.
But in order for someone to help you when you're down and out, you have to be ... down and out. Also, sometimes something is so nice it's sad. Does that make any sense to you?
8. "Trees Lounge" by Hayden
Trees Lounge, starring Steve Buscemi (a Long Island native) takes place in Valley Stream, New York, and is set decades ago mainly in a hole-in-the-wall gin-mill called Trees Lounge, where the regulars drink their depressing lives away.
Anyone who has had alcohol and/or substance abuse issues, or has had a loved one who has such issues, will be familiar with the horrible "Groundhog's Day" feel of this movie.
9. "Somewhere Only We Know" by Keane
The lyrics of this song aren't all that sad, per se, but the tone is, to me, one of desperate sadness. Do you agree? If not, don't worry, I'm the weird one.
Kenneth Avery from Hamilton, Alabama on April 24, 2015:
This was one fantastic read! Loved every word. I voted Up + all of the choices. Your graphics usage was superb. I like hubs like this. I urge you to keep up the great work and may you have a world of success on HubPages.
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DSmizzle (author) from Long Beach, New York on April 10, 2015:
Thanks for reading Cornelia!
I'm checking out some of your stuff right now.
Korneliya Yonkova from Cork, Ireland on April 10, 2015:
Awesome list. My personal favorites are The Trial by Pink Floyd and... certainly Simon and Garfunkel. :)