There are different preferences by different people as music is something that people relate to on a personal level. What is sad for one person, may be extremely hopeful for another. For me, the saddest song of all time is Love Hurts by REM. This song always gets my heart as it is full of raw emotions and love.
At the same time, it gives off a ray of hope as it portrays the feeling that you are not alone and that there are others with a similar kind of pain. The music video of this song is also sad and bring back certain memories that take you into the realms of grief.
I think the saddest, but also the most hopeful, song of all time is Love Hurts by R.E.M. This song always makes me cry because it talks about raw emotions that we all have. It is hopeful because it makes me feel like I am not alone, but sad because I know that everyone feels pain.
Even the music video for this song is really sad and emotional. It is hard to hold back the tears when you see person after person get out of their car you know they all have pain.