John Prine’s “Angel From Montgomery” that Bonnie Raitt covered about a woman trapped in a loveless marriage.
Gloomy Sunday - a.k.a hungarian suicide song
Have a nice day :(“The Happiest Girl in the Whole USA” by Donna Fargo. The lyrics tell one story, but the music sounds like she’s about to open an artery.
In what universe is Tom Waits considered pop?
“Pop” can be a very vague category. Heck, I mentioned Joy Division and Massive Attack, neither of which are your typical formulaic Top 40 types of bands, but can be “pop” under a broad definition (which is why I asked "I don’t know if you mean Top 40 by “pop music”.) I tend to use it broadly, in opposition to something like classical music, but am aware of more narrow definitions (like ones that define the Beatles as “pop,” but the Stones as “rock,” when to me, they’re both both.)
Here is an instrumental of a song of theirs called Black Sun (it does have a Singing In The Rain name to it but don’t let it fool you) 
Foreigner’s, “I Want To Know What Love Is,” is really close to a dirge, even with the lyrics.
Maybe this is stretching the genre, as I wouldn’t consider it ‘pop’ music, but if you will allow me to slightly bend the rules, this instrumental of a song has to take the cake. Hands down.
((If it turns out anyone likes it and hasn’t heard it before, I highly recommend the Johnny Cash version. Absolutely stunning.))
I know exactly the riff you referred to. I get goosebumps just thinking about it. Yes, Ode to Billy Joe definitely qualifies in my book – both the tune and the lyrics.
No link but The Weeknd, “Wicked Games”. Definitely a vibe of pain, isolation and resignation.
I guess it’s just a Friday night and i’m chilling but the song from Jimmy Eat World, “Sweetness”, while not exactly a depressing sound, has a bittersweet vibe.
This thread is incomplete without Fergie’s Big Girls Don’t Cry
Does Tracy Chapman count as pop? What about Suzanne Vega?
Pink Floyd’s In the Flesh ain’t exactly cheery-sounding.
I’m the furthest possible from an expert, but IMO if Suzanne Vega and Tracy Chapman are not pop then a pretty narrow definition must be in use. To whatever extent this thread could be considered “mine”, I don’t think there’s a good reason to go that narrow. I think it’s about gloomy-sounding music that’s not in the other broad categories - not classical, not old-time country, and so on. (For example, modern country is just pop with a twang and a hat, so go ahead if you want.)
I think I did start out with an idea that top-40 never ever has a gloomy tune, and I think I’m pretty much right about that - but the thread’s more interesting than that now.
Big Girls Don’t Cry feels like the opposite to me - a bouncy lively tune tinged with just a little bit of thoughtfulness. I sure can’t think of it as a sad gloomy piece of music. I think you’re caught by the lyrics, which can be taken as much more serious than the music.
I’m not sure what to make of this one - Holly Cole singing “Don’t Let the Teardrops Rust Your Shining Heart”
Well it might depend if you think of the song as primarily the verse or the chorus. But to me, the verse is wistful, and the chorus is determined, and none of it could be seen as bouncy.
Not bouncy personality, but physically bouncy - drums, rhythmic activity.
That song is not slow and it isn’t depressing outside of the context of the lyrics.
Oh, I know “Black Sun” very well. I’ve listened to Death Cab on and off since about 2001. I know what they do. I’m just saying it’s not all Sad Sack slit-your-wrists songs, just more mid-tempo “sensitive” indie pop or something.