I was thinking about how there are some songs that you kinda just bop along to, then when you listen to the lyrics it’s like “Well. That’s not cheerful at all.”
Examples (Sorry, I can’t link, YouTube is blocked at work):
“Veronica” by Elvis Costello - about his grandmother’s descent into dementia.
“I Don’t Like Mondays” by the Boomtown Rats - about an actual school shooting that happened in 1979. Unlike what I thought when it came out, has nothing to do with Garfield the Cat.
“Just Dance” by Lady Gaga - the singer is at a club and realizes she’s so drunk that she doesn’t know where she is or where her keys or phone are, but figures if she can just keep dancing till she sobers up a little she’ll be okay…meanwhile in the part sung by Colby O’Donis he is a random guy in the club, watching her and planning to take her home (despite her extreme intoxication). Kinda rapey.
“Alouette”, when translated, says "Lark, gentle lark/Lark I will pluck you/I willl pull your feathers off/From your (head, breast, wings, etc).
Got some other good ones?
Note: Songs that are intended as humorous/parodies (Tom Lehrer, etc) don’t count for this.
Knock On Wood by the Mighty Mighty Bosstones. It’s about hoping that you never have to deal with tragedy, and how you’re not sure you’d handle it well if it came. On the other hand, possibly the peppiest, most upbeat song to come out of third-wave ska.
“You get word before the show has started
that your favorite uncle died at dawn
Top of that, your pa and ma have parted,
you’re broken-hearted, but you go on”
I agree in general, but Can’t Stand Losing You is in a minor key only moving to major in an ironic way at the part of the lyrics that include “I guess you’d call it suicide”, not sung that fast, has that dark/weird sounding little bridge in one place, and the beat, while strong-ish, is restrained and kind of “off”. I would leave that one off the list just because there are so many better examples.
(I do have to admit that for a song that mentions suicide in such an obvious way, Can’t Stand Losing You is not THAT gloomy sounding - but I think it’s not clear that the character in the lyrics would really go through with what he’s saying.)
There is Simon and Garfunkel’s “The Sun is Burning”, a sweet little song about nuclear war. Also “7 O’clock News/Silent Night” although the lyrics themselves are not the reason.
They Might Be Giants are the king of this. Examples:
“They’ll Need A Crane” - “They’ll need a crane, they’ll need a crane / To take the house he built for her apart / To make it break it’s gonna take a metal ball hung from a chain / They’ll need a crane, they’ll need a crane / To pick the broken ruins up again / To mend her heart, to help him start to see a world apart from pain”
“I’ve Got A Match” - “You think it’s always sensitive and good / You think that I want to be understood / I’ve got a match / Your embrace and my collapse”
“Lucky Ball And Chain” - “I lost my lucky ball and chain / Now she’s four years gone / Just five feet tall and sick of me / And all my rattling on / She walked away from a happy man / I thought I was so cool/ /I just stood there whistling / “There goes the bride” as she walked out the door”
“Don’t Let’s Start” - “No one in the world ever gets what they want, and that is beautiful / Everybody dies frustrated and sad and that is beautiful”
Siouxsie & The Banshees Peek A Boo. Bouncy, playful music backing images of an abused and soul-crushed sex worker. With Siouxsie, pretty much any upbeat tune is going to have some pretty dark themes.