(5) James, "Say Something"
It’s not hard to find a sad James song; even their happy-sounding tunes are downers if you pay close enough attention (“Laid” for example). “Say Something” rose to the top for three reasons: 1. The weird, bleak video (below, apparently made for the British market—the later American video was different, though MTV also showed the British one) featuring gorillas and sexy, indifferent scientists. 2. The fondness one committee member had for this song during her wallowing-in-self-pity college days: the lyrics “More than a drug is what I need / need a change of scenery / need a new life” ring especially true when all alone in a crappy dorm room. 3. The presence of another, much worse song called “Say Something” in the world. This dumb and sappy “Say Something” dominates the searches; is being supplanted by a lousy approximation not among the saddest fates?
(12) Red House Painters, "Katy Song"
Before this song disintegrates into an increasingly spooky place in the last few minutes it occupies a forlorn and isolated place, one happy to simply echo sadness and resignation: there’s no way our speaker’s ever getting the girl back, and he knows this, hence the way it gets creepier and creepier the longer the song goes on, a nice recognition that all expressions of wistful romance become desperate and eventually pathetic, even pointless. Well, it’s never pointless to sing an ache, and maybe it’s sadder that the ache can’t be alleviated in a song. The Toronto Star has this as the 93rd saddest song of all time on their list (you’ll see several songs from this bracket on the list, which isn’t limited to our timeframe, so Samuel Barber’s “Adagio for Strings” wins it, which should give you a good idea). How do you differentiate between this at #93 and #94, Pink Floyd’s “Wish You Were Here”? Better, we think, to seed the field, as we’ve done, and play the songs, and let you all decide.