My Picks for the 20 Saddest Songs of All Time

Music can be healing, music can be inspiring and music can be releasing. Songs that strike an emotional chord are very personal. Here is a list of songs I prefer to listen too when locked up in my room and when preferably in the fetal position.

1."I'm so lonesome I could cry" Hank Williams ~ "I've never seen a night so long" "The moon just went behind the clouds to hide it's face and cry". Hank Williams wears his heart on his sleeve and the pain in his voice. "He's lost his will to live" "I'm so lonesome I could cry"

2."Tears in Heaven" Eric Clapton ~ An outpouring of strength in the face of excruciating pain. "Would you know my name, if I saw you in Heaven" "Will it be the same, if I saw you in Heaven" "Would you hold my hand, if I saw you in Heaven" A song about the loss of a child and the enormous task of having to move on.

3."I don't like Monday's" Boomtown Rats ~ A song written about a real-life event of a sixteen year old girl in California who went on a shooting spree and showed no remorse. The senseless act of violence and it's toll on innocence. "sweet sixteen ain't that peachy keen" "I wanna shoot the whole day down". "The lesson today is how to die".

4."I will always remember you" Sarah Mclachlan ~ II will remember you, will you remember me?" "Don't let your life pass you by" clinging to a past that doesn't let me choose". An emotional plea disguised with an Angel's voice. A tearful question most of us have wondered and imagined in a moment of despair.

5."Cat's in the Cradle" Harry Chapin ~ A song about how brief our time with our children really is. Inevitable pain caused by an unintentional sequence of events. "When he hung up the phone, it occurred to me, my boy grew up to be just like me"

6."Everybody Hurts" REM ~ Raw, REM seems to find that painful space in all of us. "when your day is long, and the night, the night is yours alone" "and you're sure you've had enough of this life, hang on". A plea to hold on and to understand that everyone hurts. "If you think you've had too much of this life".

7."With or Without You" U2 ~ This song live is amazing. "See the storm set in your eyes" "I'll wait for you" "slide of hand and twist of fate" "on a bed of nails, she makes me wait". Intricate, poetry in voice. "and you give yourself away". Passionate and wild.

8."Hallelujah" Jeff Buckley ~ Recently surfacing again. Jeff Buckley's rendition of this song is poignant and haunting. You feel the intensity of the broken spirit. A cry for redemption.

9."Landslide" Stevie Nicks ~ "Can I sail through the changing ocean tides, can I handle the seasons of my life?" "I don't know". Feeling the overwhelming loss when you lose sight of who you are and where you're going.

10."Yesterday" The Beatles ~ One of the most beautiful ballads the Beatles had ever recorded. "Yesterday, my troubles seemed so far way." "Yesterday, love was such an easy game to play" A sensitive wondering of what could have been and questioning why it couldn't be that way.

11."No More Drama" Mary J. Blige ~ From the real life of Mary J. Blige who suffered from depression and paranoia during a low point in her life that nearly destroyed her. "Broken heart again, another lesson learned, know your friends, or you will get burned" "No more pain, no more pain, no more drama in my life". A testament to how strong the human spirit can be. "Only God knows where the story ends for me"

12."Time after Time" Cyndi Lauper ~ "Caught up in circles, confusion is nothing new". Beautifully timeless. The sweetness that is true love. "if you fall, I will catch you. I will be waiting" "Time after Time"

13."Mad World" Gary Jules ~ From the "Donnie Darko" soundtrack. "Their tears are filling up their glasses, no expression, no expression" "The dreams of dieing are the best I've ever had" Agonizing and moving.

14."Angels" Robbie Williams ~ Sadness laced with hope. A search for unconditional love. "She won't forsake me" "I'm loving Angels instead" "She offers me protection, a lot of love and affection. Weather I'm right or wrong" "She breathes flesh to my bones"

15."Under the Bridge" Red Hot Chili Peppers ~ Triumphant but sad all at the same time. A true account of racing against the odds. Loneliness reflected. A bittersweet love story between man and his city of angels.

16."Mahogany" Diana Ross ~ "Do you know where you're going to, do you like the things that life's been showing you?" A song about looking back at what should have been.

17."Nothing Compares 2 U" Sinead O'Connor ~ "It's been 7 hours and 15 days, since you took your love away". Brilliant and heart wrenching. Honest to the core. Sinead's version sends shivers everytime.

18."Bohemian Rhapsody" Queen ~ In my opinion, one of the best songs of all time. "Mama, I just killed a man, put a gun against his head, pulled my trigger, now he's dead". Epic and remorseful regret.

19. "Voices Carry" Aimee Mann ~ "In the dark, I like to try to read his mind. But I'm afraid of the things I might find". Paralyzing fear and an emotional portrayal of torment.

20. "One" U2 ~ "Did I disappoint you, leave a bad taste in your mouth", "you act like you never had love and you want me to go without". A song about forgiveness and letting go.