The Gary Jules cover of Mad World, for the Donnie Darko soundtrack.

Similarly, the original song by Tears for Fears sounds really upbeat and happy, but you'd never know it was a sad song unless you paid attention to the lyrics. I love both versions!

Hurt by Johnny Cash.

Fast Car by Tracy Chapman.

There are a lot. I have a long playlist called "mope" But the first song that came to mind is:

"Blue Valentine" by Tom Waits. https://youtu.be/wsw0aWXufqM

Boulevard of Broken Dreams by Green Day

Mazzy Star - Into Dust

Nine Inch Nails - "Leaving Hope" and "And All That Could Have Been"

Round Here by Counting Crows

Mad World - specifically the Gary Jules version. Even Tears For Fears like what he did with it.

Had a pretty rough year last year. Dear Agony - Breaking Benjamin was my sad song of choice.

I have a few.

Sonny by New Found Glory

My December by Linkin Park

Adam's Song by Blink 182

The night we met - Lord Huron

Arms of an Angel, Sarah McLaughlan

Youth of the Nation - POD (kind of like Adam's Song).

World at Large - Modest Mouse

In the Aeroplane Over the Sea - Neutral Milk Hotel (based on Anne Franke).

To Build a Home - Cinematic Orchestra

There were some others already mentioned. Very powerful.

Depends on why I'm listening to sad music. But I'm an unrepentent goth, so Ive got a LOT if sad music. These are a few of my favourites:

• Joy Division - Love will tear us apart, New dawn fades
• Sisters of Mercy - Some kind of stranger
• Dawn Penn - You don't love me (not the Rhianna version!)
• VNV Nation - Legion. Or maybe Forsaken. Maybe all of PTF and Empires
• Ultravox - Lament
• Stanford - Songs of farewell
• Faure - Requiem

Sad to me a lot of times means stuff about time passing and getting older or things changing, so most of these are along that line. Some of the ones I think of first:

Time, Fat Old Sun, and High Hopes by Pink Floyd

In My Life by The Beatles (also Ozzy)

Hurt by Johnny Cash (orginally NiN)

Preaching the End of the World by Chris Cornell

There Was a Light Here by Demon Hunter

Landslide by Stevie Nicks/Fleetwood Mac

Jolene as covered by Jack White. Dolly Parton singing it is also great, but to me it comes off as just another country song about infidelity. When Jack White covers it, it seems to take on a whole other perspective, but I guess that also depends on the listener too and what they project onto it.

Ok, so this song is arguably more of a depression song than a sad song, but it's a great song. Pinch Me - Barenaked Ladies

Amanda Palmer's The Bed Song (YT link)

Lately I get got by Rise Against's People Live Here (YT link)

Lost Shadow by Gunship

Blonde Redhead, "For the Damaged"

"Somewhere Out There " from American Tail

The National - About Today

Radiohead - Pyramid Song

Sufjan Stevens - Carrie & Lowell (album)

How To Save A Life by The Fray

Oldie but Goldie & the saddest song I've ever heard: Gilbert O'Sullivan - Alone Again (Naturally)

All My Love by London Grammar. Retrograde by James Blake.

• Big Rude Jake -- The Diner
• Reverend Beat-Man -- Today Is A Beautiful Day
• The Dead Brothers -- Everything's Dead
• Steam Powered Giraffe - Honeybee
• The Violent Femmes -- Johnny
• Dwight Yokum -- I Sang Dixie
• Leonard Cohen -- Joan of Arc
• The Cranberries -- Zombie
• The Tragically Hip -- 38 Years Old
• Blue Rodeo -- Bad Timing
• Blue Rodeo - Hasn't Hit Me Yet

Goddamn it, OP, you've destroyed me. Thank you for listening to my mix tape.

Steve / King Park / No one was driving the car all by La Dispute

Honourable mentions for "In this shirt" by The Irrepressibles and "Ordinary Loss" by HEALTH

Deference for Darkness - Halo 3 ODST Soundtrack

The Magnetic Fields — "100,000 Fireflies"

There's the absolute classic: Halpelujah by Leonard Cohen which is just a beautiful song about the end of love

But my personal favorite is: I Will Follow You Into the Dark by Death Cab for Cutie, really the whole Plans album is amazing and wrecks me still.

When You Go, by Jonathan Coulton

Favorite is relative, usually the one I'm listening to at the moment. But I keep coming back to the Okkervil River album, The Stand-Ins. It's a companion album to The Stage Names, about the losers and also-rans, so it's full of sad songs.

My favorites, though, are the last two:

Calling and Not Calling My Ex, about a man who stagnated after breaking up with his girlfriend while she pursued her career. (Rumored to be inspired by Will Sheff's relationship with Scarlett Johansen.)

Bruce Wayne Campbell Interviewed on the Roof of the Chelsea Hotel, 1979. Campbell was the first openly-gay rock star under the name Jobriath, and now mostly forgotten. He was manipulated and exploited by his manager/agent, and retired from music in 1975 to an apartment on the roof of the Chelsea Hotel. He died there of AIDS in 1983.

Chemo limo by Regina Spektor is mine.

Beautiful song, but it can be too sad for me sometimes if I'm in a more empathetic mind frame

Glay - Kanojo

I have no idea where I first got that song, but I've had it as an mp3 for at least 20 years at this point.

Roads by Portishead.

Don’t have a specific favourite, but this is in the mix: Suicide Cargo Load

Edit: Rest of the album is as emotionally heavy.

https://www.youtube.com/watch?v=t9kT1xIpZ4E

Jacques Brel - Ne me quitte pas

Gate of Steiner

Currently it is Mother Pray for Me by The Beths

Keia by Colliding With Mars

Barry Manilow- Looks like we made it.

Hope