Probably this today. I'll change my mind tho... I used to visit all the very gay places, Those come what may places, Where one relaxes on the axis of the wheel of life To get the feel of life From jazz and cocktails. The girls I knew had sad and sullen grey faces With distingué traces That used to be there, you could see where they'd been washed away By too many through the day Twelve o'clock tales. Then you came along with your siren of song To tempt me to madness! I thought for a while that your poignant smile was tinged with the sadness Of a great love for me. Ah yes! I was wrong, Again, I was wrong. Life is lonely again, And only last year everything seemed so sure. Now life is awful again, A troughful of hearts could only be a bore. A week in Paris will ease the bite of it, All I care is to smile in spite of it. I'll forget you, I will While yet you are still burning inside my brain. Romance is mush, Stifling those who strive. I'll live a lush life in some small dive And there I'll be, while I rot With the rest of those whose lives are lonely, too…
Told you I'd change my mind... Sunday is gloomy, my hours are slumberless Dearest, the shadows I live with are numberless Little white flowers will never awaken you Not where the black coach of sorrow has taken you Angels have no thought of ever returning you Would they be angry if I thought of joining you? Gloomy Sunday Gloomy is Sunday, with shadows I spend it all My heart and I have decided to end it all Soon there'll be candles and prayers that are sad I know Let them not weep, let them know that I'm glad to go Death is no dream for in death I'm caressing you With the last breath of my soul, I'll be blessing you Gloomy Sunday
I don't have a specific saddest song, but a whole collection of songs that would qualify (which is saddest for me varies based on my mood). Among them is "The Winner Takes It All" by ABBA (although this video uses a vocaloid for the visual, it is ABBA's song):
Randy Newman, "In Germany before the War." A child murderer gets sentimental about a little dead girl. Achingly beautiful and nauseating at the same time. It's so sad I can't even listen to it.
Fantastic version. Charlie has a lot of real heartbreakers but Feel Like Going Home is the ultimate. I totally love this incredibly sad song as well.
Aimee Mann—Just Like Anyone Aimee expressing sorrow and regret after Jeff Buckley’s death. Heartbreaking.
4 pages in and no one is going to mention this?? Of course theres always this one... https://youtu.be/SMjtD-dpnOk
The Special AKA with Rohoda Dhakar - The Boiler First heard this after it was posted on another forum on a similar thread to this and has to be one of the most harrowing and saddest songs ever written.
This was one of my picks along with Suffer Little Children by The Smiths. For hit singles, I'll take Along Again (Naturally) by Gilbert O'Sullivan.
"Give My Love to Rose" by Johnny Cash I found him by the railroad track this morning I could see that he was nearly dead I knelt down beside him and I listened Just to hear the words the dying fellow said He said, they let me out of prison down in Frisco For 10 long years I've paid for what I've done I was trying to get back to Louisiana To see my Rose and get to know my son Give my love to Rose, please won't you mister Take her all my money, tell her to buy some pretty clothes Tell my boy his daddy's so proud of him And don't forget to give my love to Rose Tell them I said thanks for waiting for me Tell my boy to help his mom at home Tell my Rose to try to find another For it ain't right that she should live alone Mister, here's a bag with all my money It won't last them long the way it goes God bless you for finding me this morning And don't forget to give my love to Rose
"Fire and Rain" by James Taylor. Specifically the live perormance from the "Live At The Beacon Theatre" concert DVD with the slower tempo and beautiful, haunting cello accompaniment.