The Greatest Sad Songs of All Time

The other day, I was listening to music and I started thinking about great sad songs. I decided making a list of some of my favorites would be a pretty cool thing to do. At first, it was going to be a top ten kind of thing, but I had a really hard time narrowing it down. My apologies also go out to Broadway and church music. There are a lot of great downers in those musical traditions, but it was hard enough just narrowing down rock songs. So here is my top twenty. I am not a great music critic, but I am trying. Usually my best descriptions are "it's awesome!" or "it's lame!" and this is a "twenty best" list so they are all, for the most part, songs I like. I also tried to be diverse in my music selections. I believe Eddie Vedder is the only person to appear twice (once as a solo artist and once with Pearl Jam). Please comment to tell me what you think of my list, what songs I missed. Enjoy!

20. Creep by Radiohead

From Radiohead's 1993 album, Pablo Honey, "Creep" is one of their most popular songs. In the song, the singer is expressing his anguish with his life and wishing he was different than he is. "You're so (expletive) special. I wish I was special, but I'm a creep....I don't belong here." is the line that best expresses the mood of the song.

19. Candle in the Wind by Elton John

Elton John made two versions of this song, one about Marilyn Monroe, the other about Princess Diana. The image of living your life like a candle in the wind is an interesting one. It makes people realize how vulnerable we all are, no matter how rich and famous. Regardless of how glamorous your life may seem, you will still encounter problems like other people, but fame puts more pressure on the individual.

18. You Don't Know What Love Is (You Just Do As You're Told) by The White Stripes

This song comes from The White Stripes' 2007 album Icky Thump. In this song, the singer is explaining to someone else, that they are to naive to understand the meaning of love. He says that there is still hope that you can learn, but for now, they are too old to be having these immature perceptions of love.

17. Runaway by Yeah Yeah Yeahs

This song is from their 2009 album It's Blitz! The song begins with a simple, one note at a time, plinking on the piano and builds more and more adding drums, strings and synthesizer as the song progresses. The lyrics are about being depressed and trying to run away from it all. This album as a whole is, in my opinion, the Yeah Yeah Yeahs best work so far.

16. Leaving on a Jet Plane by John Denver

This is a great song for when you are sad or traveling. It expresses both the anticipation of an exciting trip, but also the sadness and uncertainty of leaving loved ones. It also expresses regret of not making the most of the time they had together before he is about to leave. The song also has a sad undertone because Denver died in a plane crash long after the song was written.

15. Society by Eddie Vedder

This song comes from the soundtrack of 2007 film Into the Wild. The movie tells the story of Christopher McCandless, a man who stopped talking to his family, gave away his life away to charity and hitchhiked across the country after graduating from college. He was found dead after trying to live off the land through an Alaskan winter. Vedder's song is about the greed and selfishness of today's society and how people do not always fit in. He says directly to Society, "I hope you're not lonely without me." It is a sad song on its own, but knowing the story for which it was written only adds to it.

14. In the Aeroplane over the Sea by Neutral Milk Hotel

This is the title track from Neutral Milk Hotel's 1998 album. I am not sure if this one counts as a sad song, but I always listen to it when I am feeling down. The line "And one day we will die and our ashes will fly from the aeroplane over the sea, but for now we are young. Let us lay n the sun and count every beautiful thing we can see." brings up both positive and morbid images. It reflects the tragic idealistic innocence of The Diary of Anne Frank, which inspired the album.

13. Wish You Were Here by Pink Floyd

One of my favorite Pink Floyd songs, "Wish You Were Here" pretty much explains itself and sets the mood in the title. It reflects the loneliness people feel in the line "We're just two lost souls swimming in a fish bowl."

12. Samson by Regina Spektor

This song comes from Regina Spektor's 2006 album Begin to Hope. This song has a different take on the Biblical story of Samson. The song is sung from point of view of Samson's lover, Delilah. Delilah, according to the Bible, betrayed Samson by cutting his hair (the origin of his strength) allowing him to be captured by the Philistines. In the song, she tries to plead with people that she truly loved Samson. She says that she had no choice but to cut his hair, and the history books and the Bible never mentioned her true love. This song is about the depressing concept that people are not remembered by the love they had for others but instead by their mistakes and shortcomings.

11. Old College Try by The Mountain Goats

I had a hard time deciding on this one because The Mountain Goats have a very impressive collection of sad songs in their repertoire, but I settled on "Old College Try" because a lot of their other sad songs, while depressing and morbid in lyrics, are more upbeat than this one. This song is from their 2002 album Tallahassee. It is about a relationship that is falling apart, but the singer wants to keep trying to patch things up. He realized that there is little hope and that nobody had ever really given them a chance to succeed, but he is willing to stay with her to the end, if she will stay with him.

10. Sad Songs and Waltzes by Willie Nelson

If I were more of a country music fan, there would probably be more than one country song in this list. When the songs are not about tractors or conservative politics, country singers do have a good grip on the human emotions and love and loss. To represent the genre of country, I chose arguably the best country singer (sorry Johnny Cash) ever in Willie Nelson. This song, which was also covered by the band Cake, is about a guy who want to write a song about how is ex cheated on him and broke his heart, but she has "no need to fear it, 'cause no one will hear it. 'Cause sad songs and waltzes aren't selling this year." That is a sad situation. She treats you poorly, and she breaks your heart, but you can't get back at her because nobody want to hear you sing about it.

9. Things Ain't Like They Used To Be by The Black Keys

This song is from The Black Keys' 2008 album Attack & Release. It is a great blues tune that laments on how things have changed and its about time you realize that. The song also features blues singer Jessica Lea Mayfield, who according to her Wikipedia page, specializes in sad songs. The lyrics are not overly sad or depressing without the blues notes and rhythm added, but the complete ensemble is very worthy of this list.

8. Blame it on the Tetons by Modest Mouse

This track comes from Modest Mouse's 2004 album Good News for People Who Love Bad News. "Blame It on the Tetons" contrast from the other tracks on the album because it is slower and quieter. While lead singer Isaac Brock shouts in other tracks, he sings softly in this one. Other tracks contain brass and louder electric guitars, while this one has a violin, an acoustic guitar, piano and bass and the drummer uses brushes instead of sticks. The change in instrumentation helps set the mood. The defining line for me in this song is "Everyone's a building burning with no one to put the fire out." This song is the biggest downer in a mostly negative album.

7. Cat's in the Cradle by Harry Chapin

This song scared Harry Chapin. This song scares me. From his 1974 album Verities & Balderdash, this song is about being a parent, but working to hard to get to enjoy it. In all of the major events in his son's life, the father always has "planes to catch and bills to pay". By the end, his son is grown up and he is retired. He wants to spend time with his son, but his son is too busy with work. All his life the son said he wanted to be just like the father, and in the end he did. If I ever become a parent, this song will be stuck in my head for the rest of my life and I will be terrified of ending up like the guy in the song.

6. Crown of Love by Arcade Fire

Arcade Fire is one of my favorite bands and I have been listening to them almost nonstop for about five months now. This track, from the 2004 album Funeral is their saddest sounding song. The singer repeatedly says "if you still want me, please forgive me" and he is trying to retrieve his crown of love while fighting through the pain of loss. If you have not listened to this band, I highly suggest that you give them a chance because they are awesome.

5. Everybody Hurts by REM

This is one of the great songs that recognizes that we all feel bad sometimes. Everybody cries. Everybody hurts, sometimes. Things will not always be right but keep holding on. This is a great song to listen to when you are in a bad mood and need reassurance. No matter the situation, it seems like R.E.M. is always empathetic and ready to listen to your problems when you hear this song. There is another song very similar to this one later in the countdown, so keep reading.

4. Yesterday by The Beatles

When Paul McCartney wrote "Yesterday", the tune and lyrics came so easily to him that he thought it had already been written. He thought he was copying the Rolling Stones because it was so easy to write. As simple as this song may seem, the feeling in it is profound and nearly fifty years later, it still seems relevant. "Why she had to go, I don't know. She wouldn't say. I said something wrong, now I long for yesterday." We all have those days when you feel like you could have done better to make things less painful, but it is too late to change anything now.

3. Bridge over Troubled Water by Simon & Garfunkel

This song is the one that I think is similar to the above mentioned "Everybody Hurts". We all go through tough times, but with friends, we can get through it. When you are weary, feeling small, when tears are in your eyes, Art Garfunkel will help you out like a bridge over troubled water. This is a great song by one of the best duets in the history of music. When nobody else is there for you, Paul Simon and Art Garfunkel will always be there. Also, "Lean on Me" by Bill Withers should be an honorable mention for this list.

2. Last Kiss by Pearl Jam

Number one and number two could be flipped and I would be okay with it. They are both very sad ballads. Pearl Jam comes in at number two with "Last Kiss". This is a song about a guy who lost the love of his life in a car crash. He feels like it was his fault for swerving to avoid a stalled out car. His girlfriend gets the full impact of the crash and she dies in his arms. It is an incredibly tragic turn of events. His only hope for the rest of his life is that he behaves himself well enough to be able to see her again in heaven.

1. Lost Cause by Beck

Like I said before, these last two are very close and about equally brilliantly sad, in my opinion. The number one greatest sad song goes to Beck for his song "Lost Cause". This track is from his 2002 album Sea Change. I cannot effectively describe how great this song is, but I will try. The lines about seeing people he used to know who just pass him by and are indifferent to one another frightens and depresses me. Growing up in a small town, I know what it is like to see people around that you used to know but have not talked to in years. "This town is crazy. Nobody cares." This song hits terribly close to home but is way off at the same time. The other depressing theme of this song is being tired of fighting for a lost cause. I personally know how depressing it is when you work hard at something that nobody else seems to care about. You keep pressing on, but it can be demoralizing to keep trying with no return. You do not always want to accept that it is a futile effort, but eventually it seems that it is a lost cause.