There are some songs so heart wrenching and tragic, they're difficult to even hear. And when you're really depressed, they're the best songs to listen to. Why? I think because they acknowledge the difficulties we all face and just tell the story of a struggle that threatens to overcome us.
So, without further ado, here they are:
Red Dirt Girl by Emmy Lou Harris - It never really says that the red dirt girl was part of the Appalachian mountain poor but it does leave that impression. The singer was best friends with her while growing up but she watches helplessly as her friends' life unwinds and she is eventually overcome. The red dirt girt tries everything she should to straighten herself out but never seems to catch a break.
Someday Never Comes by Creedence Clearwater Revival - The singer recalls the difficulty and sadness of his parents divorce only to be crushed a second time when, later in life, he finds himself in his father's position, explaining to his son that maybe some day he'll understand. But that day never came for him.
Boots of Spanish Leather by Bob Dylan - A young couple bid each other farewell as the woman departs on a sea voyage. She asks her guy if he wants anything as a present from far away Spain but all he really wants is her return. They depart and after time passes, he gets a letter from her expressing an unexpected ambivalence on returning. The guy figures out his standing and finally asks for a gift of Spanish boots made of Spanish leather. It leaves you wondering if perhaps it was always her intention to offer him a parting gift.
Dress Rehearsal Rag by Leonard Cohen - An honest and straight forward contemplation of ending it all comes to the singer as he is shaving and standing in front of the mirror looking at himself. He reviews his life and wonders if there is any hope. In the end, he decides there is so it's only a dress rehearsal and not a call for the final curtain. In one of the rare live recordings of this song, he admits to avoiding performing this song as much as he can.