If someone else is suffering enough to write it down
When every single word makes sense
Then it’s easier to have those songs around
The kick inside is in the line that finally gets to you
and it feels so good to hurt so bad
And suffer just enough to sing the blues
-Elton John
Elton is right, as usual. Sad songs do say so much. I’m somewhat of a sad song addict. I have no explanation or neat story to explain why I like them, but I wish I did- I have always found them oddly comforting. Forced to come up with some explanation, I’d likely say that the very best sad songs draw out emotion and emotion makes one feel real, alive, and excited and the feeling of being real, alive, and excited doesn’t happen as much as I wish.
To summarize: sad songs = emotion = real/alive/exciting = rare.
Sad is a broad word, though. To narrow it a bit, I should say that I do not consider sad a synonym of depressing. I do not like depressing songs. Depressing songs (of the Jeff Buckly, Kurt Cobain, The Smiths variety) seem pessemistic, and have less value to me. I don’t need a song to say, “Life is terrible. It has always been terrible. Suffer and then die.”
Instead, I like sad songs. Sad songs are optimistic, becase they are about loss. And to lose something you must have had something; the potential of having something is optimistic. A sad song embraces the pain of not having something you once did, and that is always better than not having ever had anything.
All of that to say that I love sad songs and will now countdown my 10 favorite sad songs. It’s entirely subjective and the ranking is a complex product of feelings entirely personal. But I’d be interested to hear your thoughts and your own sad songs.
—
HONORABLE MENTIONS:
Yesterday, The Beatles
Calling All Angels, Jane Sibbery
Hear You Me, Jimmy Eat World
Dance with My Father, Luther Vandross
Missin’ You, Sister Hazel
—
TEN: My Dear Old Friend, Mary Chapin Carpenter
NINE: Hide and Seek, Imogen Heap
EIGHT: Wind Beneath My Wings, Bette Midler
SEVEN: Losing You, Randy Newman
SIX: Man of the Hour, Pearl Jam
FIVE: Walk Away, Ben Harper
And once again that rising sun is droppin’ on down
And once again, you my friend, are nowhere to be found.
FOUR: Tears in Heaven, Eric Clapton
Time can bring you down, time can bend your knees
Time can break your heart, have you begging please…begging please
THREE: And So It Goes, Billy Joel
And this is why my eyes are closed
It’s just as well for all I’ve seen
And so it goes, and so it goes
And you’re the only one who knows
TWO: My Sundown, Jimmy Eat World
Good goodbye lovely time
Good goodbye tinsel shine
Good goodbye
I’ll be fine
ONE: I Shall Not Walk Alone, Blind Boys of Alabama
Beauty that we left behind
How shall we tomorrow find
Set aside our weight in sin
So that we shall live again
—
There are a thousand similar lists if you want to peruse. Start here…
ThirtySomething 
My favourite from this list is the Ben Harper song. Good choice.
I like your reasoning for why people like sad songs, it makes sense and it has something I have often wondered about myself and my tastes. There is a fine line, though, between what you would call a sad song and a depressing song, and I guess it is down to personal taste.
For the record, my favourite sad song is “Casimir Pulakski Day” by Sufjan Stevens. I don’t think it would come under your ‘depressing song’ description because the melody is bright and beautiful, in spite of the song being about a loved one dying of cancer. You should check it out.
There are also a lot of unsigned artists writing incredibly sad songs. One such that I recently got into is a guy called Barnaby Griffin, his songs are about relationships and love, and his song “Sad Eyes” has a wonderful narrative. You can here it here, along with his other sad songs.