The Saddest Songs

Here is my take on the saddest songs I have heard for various reasons. In no particular order -

Casimir Pulaski Day by Sufjan Stevens

I listened to this song about half a dozen times thinking it was a fun upbeat little ditty before I listened to the lyrics. Turns out it is an incredibly sad song about a friend who has died of cancer.
Sad line - In the morning when you finally go the nurse runs in with her head hung low.

When The Tigers Broke Free by Pink Floyd

A haunting song that Pink Floyd only ever released on their greatest hits album as far as I know. It come from the movie "The Wall" and is a true account of Roger Waters Dad. The emotion in the last line sung makes this particularly moving
Sad line - that's how the high command took my Daddy from ME!

Alone Again Naturally by Gilbert O'Sullivan

Just a sad song about being alone.
Sad line - Alone again naturally

The Promise by Tracy Chapman

A song I had never heard until very recently. Very sad especially for those missing someone. The live version seems to have even more impact too.
Sad line - remembering your touch, your kiss, your warm embrace

Break Your Heart by Barenaked Ladies

A song about not having the courage to break up with someone you no longer want to be with. A great song live and sung with good emotion.
Sad line - just stop wasting my time! and now I know you'll be ok and that I've got what I want and that's rid of you - goodbye

The Freshman by The Verve Pipe

Song about a girl that he broke up with and then she committed suicide.
Sad line - I won't be held responsible she fell in love in the first place.

Black by Pearl Jam

I never really knew what this song was about until I had a look at the lyrics a few years ago and it is incredibly sad. It is a song about lost love.
Sad line - I know some day you'll have a beautiful life, I know you'll be a sun in somebody elses sky but why, why, why can't it be mine