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An on-going list of the saddest songs people know.
If you would like to add a song, send me an email.

You Are My Sunshine by Johnny Cash
Lydia by Slaid Cleaves
How to Disappear Completely by Radiohead
Sad Songs and Waltzes by Willie Nelson
The Way I Feel Inside by The Zombies
Nothing Gets Crossed Out by Bright Eyes
Long Black Veil by Lefty Frizzell
The Other Side by David Gray
He's Coming to us Dead by Grayson and Whitter
I Will Remember You by Sarah McLachlan
November by Azure Ray
Are We There Yet by Ingrid Michaelson
A Quitter by Rasputina
Call It Off by Tegan and Sara
Amie by Damien Rice
The End of The World by Skeeter Davis
Darker With the Day by Nick Cave
So Long, Farewell by Motion City Soundtrack
November Rain by Guns and Roses
Jesus Doesn’t Want Me For A Sunbeam by Nirvana
Open Up Your Heart by The Rapture
Never Dreamed You'd Leave In Summer by Stevie Wonder
Christmas Day by Jim White
Gravedigger by Dave Matthews Band
Last Flowers by Radiohead
Parasite by Nick Drake
Naked As We Came by Iron and Wine
Wonderwall by Oasis
The Moon by Cat Power
Chicken Wire by Pernice Brothers
Don't Think Twice, It's All Right by Bob Dylan
Tears in Heaven by Eric Clapton
Martha by Tom Waits
Downhearted Blues by Muddy Waters
Pain In My Heart by Otis Redding
Eleanor Rigby by The Beatles
Chelsea Hotel by Leonard Cohen
Angie by The Rolling Stones
Mad World by Gary Jules
Once I Was by Tim Buckley
The Sound of Silence by Simon And Garfunkel
Slow Show by The National
It's Just Me by Blue October
I Don't Love You by My Chemical Romance
Last To Know by Three Days Grace
Sleeper 1972 by Manchester Orchestra
Leaving on a Jet Plane by John Denver
I Didn't Understand by Elliott Smith
She's Leaving Home by The Beatles
Putting the Dog to Sleep by The Antlers
Lady Day by The Felice Brothers
Wild is The Wind by Cat Power
King's Crossing by Elliott Smith
To Build a Home by Cinematic Orchestra
Rock n' Roll Suicide by David Bowie (Jenny Lewis version)
Lime Tree by Bright Eyes
Wild Tigers I Have Known by Emily Jane White
White Face, Black Eyes by Andrew Jackson Jihad
This is the Thing by Fink
Hope There's Someone by Antony & the Johnsons
Company by Rickie Lee Jones
Simple Song by Lyle Lovett
Nobody's Crying by Patty Griffin
Hallelujah by Jeff Buckley
The Sad Waltzes of Pietro Crespi by Owen
On Your Porch by The Format
Katy Song by Red House Painters
Little Person by Jon Brion
This Is My New Vow by Jennifer Kimball
Nothing Compares To You by Sinead O'Conner
Wish You Were Here by Pink Floyd
New Slang by The Shins
You Can Close Your Eyes by James Taylor
Missing by Everything But The Girl
Pontiac by Lyle Lovett
Johnson's Love by Dwight Yoakam
Floyd County by Dwight Yoakam
Bring Him Home from Les Miserables
Leah by Roy Orbison
The Comedians by Roy Orbison
Seasons In The Sun by Terry Jacks
The Lighthouse's Tale by Nickel Creek
Eye of the Hurricane by David Wilcox
These Days by Jackson Browne (live version)
County Line by Cass McCombs
Everybody Hurts by REM
Crying by Roy Orbison
Casimir Pulaski Day by Sufjan Stevens
My Dream Girl Don't Exist by Neutral Milk Hotel
In My Life by Johnny Cash
World at Large by Modest Mouse
I Know It's Over by The Smiths
Liar by Mumford and Sons
Nothing Comes Out by The Moldy Peaches
The Sprawl I (Flatland) by The Arcade Fire
I Got It Bad (And That Ain't Good) by Ella Fitzgerald
Lord, I'm Discouraged by The Hold Steady
I Don't Want To Let You Go by Weezer
The Longing by The Eels
Colorblind by The Dresden Dolls
Just Us (For my friend Robert, who doesn't live here anymore) by Milo
R.I.P Burn Face by Cocorosie
I Know It's Over (The Smiths cover) by Jeff Buckley
Lover, You Should've Come Over by Jeff Buckley
I Am Still Here by Damien Jurado
Rita by Bebo Norman
Into the West by Annie Lennox
Hey, That's No Way to Say Goodbye by Leonard Cohen
Jackie and Edna by Kevin Coyne
Roads by Portishead
Of the Sea by A.A. Bondy
Kettering by The Antlers
Harbour by Moby Feat. Sinead O'Connor
Jolene by Dolly Parton
How Dear This Ear of Reason, Beneath The Backlit Sun by Celer
Pitseleh by Elliott Smith
Indifference by Pearl Jam
The Drugs Don't Work by The Verve
Little Blue Girl by Nina Simone
The Shortest Story by Harry Chapin
February by Dar Williams
Sometimes I Don't Know What to Feel by Todd Rundgren
A Good Year For The Roses by George Jones
Never Get to Know by Paul Baribeau
Cancer by My Chemical Romance
One by U2
Black by Pearl Jam
At Seventeen by Janice Ians
You Could Be Happy by Snow Patrol
I'm So Depressed by Abner Jay
Miss You by Trentemøller
Cycles by Frank Sinatra
Baltimore by Randy Newman
Woman Driving, Man Sleeping by The Eels
Everything must Change by Nina Simone
Gorecki's Symphony no. 3
El Noble Engaño by Los Huracanes del Norte
Kathleen by Townes Van Zandt
Upward Over the Mountain by Iron and Wine
What Happens When the Heart Just Stops by The Frames
Slip Slidin' Away by Paul Simon
Before You Leave by Mary Gauthier
The Bed Song by Amanda Palmer
Never Be Mine by Kate Bush
Goodbye My Lover by James Blunt
The Little Girl and The Dreadful Snake by The New Lost City Ramblers
Landslides by Fleetwood Mac
Everyday Is Like Sunday by Morrissey
Cat's In the Cradle by Harry Chapin
Gone Away by The Offspring
Last Kiss by Wayne Cochran
Dark Night of the Soul by Philip Wesley
Old Man by Neil Young
Strange Fruit by Billie Holiday (written by Abel Meeropol)
Nude by Radiohead
Witness by Sarah Maclaughlin
Le Vent Nous Portera by Noir Desir
Been So Long by Phosphorescent
Cactus by David Bowie
Hurt by Nine Inch Nails sung by Johnny Cash
Story Musgrave by Scrawl
New York by Snow Patrol
Oh Comely by Neutral Milk Hotel
I Will Follow You Into The Dark by Death Cab For Cutie
Are you Leaving Me by Aretha Franklin
Cold Case Love by Rhianna
Meant by Elizaveta
Kettering by The Antlers
All I Could Do Was Cry by Etta James
Congratulations by Vesta Williams
Abraham, Martin and John by Moms Mabley
Once a Blue Planet by Jean-Luc Ponty
Not Yet Remembered by Harold Budd/Brian Eno
I'm Lonely, But I Ain't That Lonely Yet by The White Stripes
Wild Is The Wind by David Bowie (Nina Simone)
Shame by PJ Harvey
Va Lumiere by Premiata Formera Marconi
Don't Mind Me, I'm Only Dyin' Slow By Jackie Greene
Serve You Right to Suffer by John Lee Hooker
Take It All by Adele
Puff the Magic Dragon by Peter Paul & Mary
Moon and the Sky by Sade
A Felicidade by Tom Jobim and Vinicius de Moraes
Youth by Daughter
Crosses by Jose Gonzalez
Game For Fools by Jaome Liddell
Flashback by Fat Freddy's Drop
Avril 14th by Aphex Twin
The Living by Natalie Merchant
My Skin by Natalie Merchant
Lighthouse by Antje Duvekot
Your Long Journey by Robert Plant and Alison Krauss
Alameda by Elliot Smith
Re:Stacks by Bon Iver
Walk on by Isaac Hayes
Volver by Vicente Fernandez
3rd Planet by Modest Mouse
Ripple by Max Cooper
Tennessee Waltz by Various (Fiddle Version)
If I Die Young by The Band Perry
Another Day by Mortal Coil w/ Elizabeth Fraser
Sergey's Ballad by Sergey Starostin's Vocal Family
Horovel (The Ploughman) by Komitas Vardapet
Eleanor Rigby by The Beatles
Big Pimpin' By Jay Z
If It Means A Lot To You by A Day To Remember
Verdi Cries By 10,000 Maniacs
The Shadowlands by Ryan Adams
Falling Slowly by Glen Hansard and Marketa Irglova
Southern CA Wants To Be Western NY by Dar Williams
Goodbye Forever by Alkaline Trio
Me Cuesta Tanto Olvidarte by Mecano
Sideshow by Blue Magic
The Bonnie Banks O' Loch Lomond
Old Rugged Cross by Various
Harvest Moon by Neil Young
Paper Bag by Fiona Apple
Raining in Baltimore" by Counting Crows
Patches by Clarence Carter
He Stopped Loving Her Today by George Jones
Poison and Wine by The Civil Wars
Miss Misery by Elliot Smith
Solitary Man by Johnny Cash
That's My Job by Conway Twitty
Tears in Heaven by Eric Clapton
Holocene by Bon Inver
Rock Bottom by Eminem
Jar of Hearts by Christina Perri
Talking Old Soldiers by Elton John
One Of Us Can't Be Wrong by Father John Misty
All Those Yesterdays by Pearl Jam
Fix You by Coldplay
To Build A Home by The Cinematic Orchestra
I'm So Lonesome I Could Cry by Hank Williams
Sunday Morning Coming Down by Johnny Cash
Sometimes It Snows In April by Prince
Sky Blue and Black by Jackson Browne
Waves by Sam Baker
Lake Charles by Lucinda Williams
I Drink by Mary Gauthier

You can listen to all the songs here.

Thanks for contributing goes to:
Will, Ben, Liz, Jonathan, Jackie, Erin, Brittney, Tanya, David, D.S., Olga, Amanda, Meg, Dora, Sara, Tommaso, Sara, Rubin, Stephanie, Gloria, Echo, Amanda, Sophia, Karolle, Rob, Evan, Ellen, Patrick, Amanda, Mike, Molly, Agnieszka, Dorota, Helen, Adeline, Elizabeth, Christian, Joan, Meg, Susan, Ian, Laura, Andi, Willow, Chris, Victoria, Barbara, Vinaya, Ramey, Francis, Christina, Joey, Melody, Lynn, John, Shannon, Rosavida, Jono, Danielle, Cheyenne, Caroline, Holly, Allen, Alexandra, Steph, Sarah, Jessica, Beatriz, Suzanne, Rick, Kelly, Cliff, Mackenzie, Bryanna, Kendra, Nora, Beth, Melody, Alexandra, Justin, Becky, Anthony, Heidi, Marlene, Eric, Evelyn, Tabitha, Bill, Anna, Laena, Claire, Joe, Andrea, Mimi, Bonnie, Dillon, Jason, Robert, Drew, Muck, Derek, Patrick, Quan, Jessica, Ann, Zach, Ava, Sara, John, Joe, Viv, Angela, Paul and all the others!