Saddest. Songs. Ever.

Here is a devastating list of the saddest songs ever. Contributed by friends and acquaintances. This would be the perfect accompaniment if you were hosting a Cry Party. Or if you were whoopin’ it up with friends and you wanted to bring the mood way the fuck down.

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[expand title=”Mary Chapin Carpenter -I Am A Town”]

(Contributed by Wes Modes)

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[expand title=”Yo La Tengo – Tears Are In Your Eyes”]

(Contributed by Chris Hirst)

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[expand title=”Kilkelly”]
http://www.youtube.com/watch?v=N76kAivCb20
(Contributed by Andrea Louise Dawson Webster)

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[expand title=”Richmond Fontaine – The Janitor”]

(Contributed by Nydia Cecilia)

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[expand title=”Don McLean – American Pie”]

(Contributed by Wes Modes)

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[expand title=”The Decemberists – Eli, the barrow boy”]

(Contributed by Sean Rbrt)

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[expand title=”Raffi – Baby Beluga”]
http://www.youtube.com/watch?v=OQYg8LKEPjA
(Contributed by Ryan Wade)

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[expand title=”The Smiths – I Know It’s Over”]
http://youtu.be/5sQPZ9dD9v8
(Contributed by Rob Simons)

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[expand title=”Hurt – NIN (Johnny Cash version).”]

(Contributed by Fehkor MacFakerson)

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[expand title=”T.B. Sheets – Van Morrison”]

(Contributed by Joe Williams)

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[expand title=”Diamanda Galas – Gloomy Sunday”]
http://www.youtube.com/watch?v=KzWVWY5QUzg
(Contributed by Margaret Kiljoy)

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[expand title=”Nick Cave And The Bad Seeds – She Fell Away”]

(Contributed by Margaret Kiljoy)

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[expand title=”Tomorrow Is A Long Time – Bob Dylan (Original Version)”]
http://www.youtube.com/watch?v=-N9Kg6DqGfc
(Contributed by Marisa Villarreal)

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[expand title=”Judy Garland – Over The Rainbow (as Hobo)”]

(Contributed by Jacob Garbe)

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[expand title=”Simon and Garfunkel – Bridge Over Troubled Water”]

(Contributed by Marisa Villarreal)

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[expand title=”Tim Hardin – Hang on to a Dream”]

(Contributed by Joseph Carter)

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[expand title=”How To Disappear Completely”]

(Contributed by Jacob Garbe)

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[expand title=”Gomez – We Haven’t Turned Around”]

(Contributed by Marisa Villarreal)

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[expand title=”Terry Jacks – Seasons In The Sun”]
http://youtu.be/rhQ13geD2OA
(Contributed by Tracey Walker)

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[expand title=”Glen Hansard – Leave”]

(Contributed by Marisa Villarreal)

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[expand title=”Sam Stone – John Prine”]

(Contributed by Joe Williams)

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[expand title=”Maura O’Connell with Karen Matheson – Down by the Salley Gardens (1998)”]

(Contributed by Tiffany Jo Waddell)

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[expand title=”John Prine – Lake Marie”]

(Contributed by Wes Modes)

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[expand title=”Nirvana – Where did you sleep last night – Unplugged in new york”]
http://www.youtube.com/watch?v=mcXYz0gtJeM
(Contributed by Jennifer Fleming)

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[expand title=”Chumbawamba – By and By”]

(Contributed by Joe Williams)

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[expand title=”Joy Division – Love Will Tear Us Apart”]
http://www.youtube.com/watch?v=GL9rSAz_oc4
(Contributed by Jennifer Fleming)

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[expand title=”Jim Croce – Operator (Live)”]
http://www.youtube.com/watch?v=FPu_G-T28iU
(Contributed by Wes Modes)

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[expand title=”Redford (for Yia-Yia & Pappou) – Michigan, 14/15″]
http://www.youtube.com/watch?v=0-SKD2D6cBA
(Contributed by Marisa Villarreal)

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[expand title=”Greg Laswell – And Then You”]

(Contributed by Julie Anna Teague)

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[expand title=”The Replacements – Unsatisfied”]
http://www.youtube.com/watch?v=ub75Sk1Wrcc
(Contributed by Marisa Villarreal)

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[expand title=”The Replacements – Achin’ to Be”]

(Contributed by Marisa Villarreal)

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[expand title=”Sufjan Stevens – Casimir Pulaski Day”]

(Contributed by Julie Anna Teague)

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[expand title=”Bon Iver & St. Vincent – Roslyn”]

(Contributed by Marisa Villarreal)

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[expand title=”Linda Perry & Grace slick – Knock Me Out”]
http://www.youtube.com/watch?v=UE6A3Reqqxk
(Contributed by Joe Williams)

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[expand title=”Carmen Mcrae Miss Otis Regrets 1980″]

(Contributed by Joe Williams)

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[expand title=”White Lion – When the Children Cry”]
http://www.youtube.com/watch?v=MHZ79InLGRY
(Contributed by Joe Williams)

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[expand title=”Kris Kristofferson – Casey’s Last Ride”]

(Contributed by David Seaman)

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[expand title=”Elliot Smith – King’s Crossing”]

(Contributed by Finn Arak)

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[expand title=”Rod Stewart – The Killing of Georgie (Part I and II)”]
http://youtu.be/skoLCUj1SwI
(Contributed by Wallace Baine)

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[expand title=”Star Anna & The Laughing Dogs – Alone In This Together (Live on KEXP)”]

(Contributed by David Seaman)

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[expand title=”The Great Lake Swimmers – Changing Colours”]

(Contributed by David Seaman)

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[expand title=”Our Town – Iris DeMent (H.Q.)”]

(Contributed by Jeremiah Daniels)

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[expand title=”Mazzy Star – Into Dust”]

(Contributed by Adrian Nankivell)

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[expand title=”The Mamas & The Papas – Monday Monday”]

(Contributed by Add Wilson)

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[expand title=”Metallica – One (Official Music Video)”]

(Contributed by Add Wilson)

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[expand title=”Soul Asylum – Runaway Train”]

(Contributed by Add Wilson)

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[expand title=”Upside Drown – Go (at Black Butte Center for Railroad Culture)”]
http://m.youtube.com/watch?v=xu45mYuEMPQ
(Contributed by Jen Nifer)

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[expand title=”Leonard Cohen – I’m your man”]
http://www.youtube.com/watch?v=iW8rFho6In8
(Contributed by Jessica Bender)

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[expand title=”Ray LaMontagne- Empty”]

(Contributed by Mike Parisi)

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[expand title=”Leonard Cohen – Dance me to the end of love”]

(Contributed by Jessica Bender)

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[expand title=”Morphine – Gone For Good”]
http://www.youtube.com/watch?v=4Rb-tTiCtPc
(Contributed by Sierra Howard Murphree)

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[expand title=”Peter, Paul, And Mary – Puff The Magic Dragon (Live 1965)”]
http://www.youtube.com/watch?v=RC2tlNmz4ao
(Contributed by Kischka Bluspiro)

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[expand title=”Karen Dalton – Katie Cruel”]
http://www.youtube.com/watch?v=raLXnnlPI_I
(Contributed by Josefina Rocha)

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[expand title=”Bj√∂rk – Gloomy Sunday.”]
http://www.youtube.com/watch?v=kr7PtJAesA8
(Contributed by Joe Williams)

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[expand title=”nina simone – strange fruit”]

(Contributed by Joe Williams)

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[expand title=”Sinead O’Connor & Roger Waters – Mother”]
http://www.youtube.com/watch?v=T2Z9L16eDpU
(Contributed by Joe Williams)

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[expand title=”Dr.John & Odetta – Brother Can You Spare a Dime”]

(Contributed by Joe Williams)

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[expand title=”Some Say Leland – Hunchback (Local Live)”]

(Contributed by Sean Zenobia)

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[expand title=”Catherine Wheel – Descending Babe”]

(Contributed by Mike Parisi)

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[expand title=”Des Ark – Peace to you too, motherf*cker”]
http://www.youtube.com/watch?v=J6L8-7FGVr0
(Contributed by Fennec Oak)

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[expand title=”Al Green – How Can You Mend A Broken Heart”]

(Contributed by Wes Modes)

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[expand title=”Ani DiFranco – You Had Time”]

(Contributed by Wes Modes)

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[expand title=”Damien Rice – Older Chests”]

(Contributed by Jacob Garbe)

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[expand title=”Seems so long ago, Nancy – Leonard Cohen”]
http://www.youtube.com/watch?v=HcZ-55lOQv4
(Contributed by Joe Cantrell)

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[expand title=”Tom Waits – Georgia Lee”]

(Contributed by Wallace Baine)

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[expand title=”Anne Briggs – Go Your Way”]

(Contributed by Jo Isaacson)

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[expand title=”Abner Jay – I’m So Depressed”]

(Contributed by Jo Isaacson)

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[expand title=”Ted Hawkins- Sorry You’re Sick”]
http://www.youtube.com/watch?v=1fGA90gaweU
(Contributed by Joe Cantrell)

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[expand title=”Simon & Garfunkel – The Dangling Conversation”]

(Contributed by Jeannette Crow)

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[expand title=”I Can’t Make You Love Me – Bonnie Raitt (1991)”]
http://www.youtube.com/watch?v=xfwylq9ZDyw
(Contributed by Jeannette Crow)

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[expand title=”George Michael – Kissing a Fool”]
http://www.youtube.com/watch?v=ZUM7Zi7CCyk
(Contributed by Jeannette Crow)

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[expand title=”Low – Weight of Water”]

(Contributed by Joe Cantrell)

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[expand title=”Belle & Sebastian-Beautiful”]

(Contributed by Joe Cantrell)

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[expand title=”Joey+Rory – When I’m Gone”]

(Contributed by Daniel DeFabio)

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[expand title=”Smog – I Break Horses (1999)”]

(Contributed by Kasey Feral Smith)

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[expand title=”Willie and Lukas Nelson – Just Breathe (Pearl Jam cover)”]

(Contributed by Daniel DeFabio)

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[expand title=”Nick Drake- Riverman”]

(Contributed by Espresso Buzz)

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[expand title=”Ooh Child – Beth Orton”]
http://www.youtube.com/watch?v=zyTOD7IlyYg
(Contributed by Daniel DeFabio)

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[expand title=”Roberta Flack – Jesse”]

(Contributed by Wes Modes)

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[expand title=”Big Bird at Jim Henson’s Memorial”]

(Contributed by Dave Dirk and Marisa Villarreal)

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[expand title=”One Tin Soldier”]

(Contributed by Kate Compton)

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[expand title=”Harry Nilsson – Without You 1972″]

(Contributed by Jami Losurdo)

[/expand]

[expand title=”Smoking Popes – Pretty Pathetic”]

(Contributed by Kenan Sharpe)

[/expand]

If you have more songs, please add them to the comments along with a YouTube link.

3 thoughts on “Saddest. Songs. Ever.

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