I listen to many songs that are arguably very sad and, perhaps, completely depressing. One of my favorite bands is Bella Morte (beautiful death) and they sing almost exclusively about the pain of living and death.
But this, this is the most depressing song I’ve ever heard. Because in my time I have lived and loved and lost. And while losing someone you love for any reason whether it was death, distance, divergent desires, or misconception, hurts; that isn’t the worst pain you can feel.
The worst pain you can feel is hope. Seems crazy but hear me out. Hope can be a wonderful thing. But misplaced hope is destruction. It eats its way through everything you are until you are left riddled with holes filled with pain.

So, the most depressing song, for reals: