It's not dark yet by bob dylan./////////////////////////////////////////////
Evanescence create some of the darkest sadest songs that I've heard some by them are the last song I'm wasting on you , lithium , my immortal How could have u guys missed out MY Immortal ??? And also exodus ,hello and your star o and also leave out all the rest by linkin park (even it's Amvs are sad )
The saddest song ever I guess would be ''Right Here Waiting'' by Richard Marx.