“Last Kiss” the Pearl Jam version

And honorable mention to:

“The Last Remaining Light” by Audioslave

• 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.

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

The National - About Today

Radiohead - Pyramid Song

Sufjan Stevens - Carrie & Lowell (album)

Amanda Palmer’s The Bed Song (YT link)

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

Haunted by Deep Purple. https://m.youtube.com/watch?v=bigkSWMEUQ0

Adam’s Song by Blink 182

Your heart is a muscle the size of your fist by Ramshackle Glory

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.

"Somewhere Out There " from American Tail

The Living Years - Mike + The Mechanics

As I get older, it gets harder to listen to it.

Roads by Portishead.

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.

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

Blonde Redhead, “For the Damaged”

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!