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!
Agreed, in a similar vein I am reminded of Dear God by XTC.
That is such a great cover.
Hurt by Johnny Cash.
As much as I admire and respect Johnny Cash, I prefer the original bij Nine Inch Nails . Paging /c/unpopularopinion
The different renditions tell slightly different stories IMO. There’s also a very fine bardcore version by Hildegard von Blingin’ that changes it to the story of a regretful immortal by only altering maybe 20% of the lines. I like all three versions for different reasons.
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
Thats cheating.
Round Here by Counting Crows
Mad World - specifically the Gary Jules version. Even Tears For Fears like what he did with it.
Nine Inch Nails - “Leaving Hope” and “And All That Could Have Been”
Had a pretty rough year last year. Dear Agony - Breaking Benjamin was my sad song of choice.
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.
I have a few.
Sonny by New Found Glory
My December by Linkin Park
Adam’s Song by Blink 182
Great song, but in my personal opinion, Smashing Pumpkins cover is better, even though I don’t like them as a band.
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
“Hanging on in quiet desperation is the English way…”
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
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.









