So I've compiled five of my favourite chipper sad songs from the 50s and 60s, in order of how much I like the song, but not necessarily how chipper (or sad) they are.
1/ This Diamond Ring by Gary Lewis and The Playboys
The song is about a guy selling an engagement ring because his fiancée cheated on him. But it's got a chirpy little bell in it, and you will most undoubtedly snap your fingers and tap your feet along to it.
SIDENOTE: This was always one of my favourite songs. Several years ago, my dad told me about how he and his siblings had the single of this song when it came out and apparently it was so risque that they had to hide it and would listen to it over and over whenever their parents left them home alone. I tried to get my musician ex-husband to do a sweet ass cover of this song--I mean, how fricking awesome is that bass line?--but as far as I know, he never did. If anyone ever does one, link me!
2/ A Boy Named Sue by Johnny Cash
Johnny Cash is not so super famous for the happy sounding songs, but this one is supposed to be funny even though the boy's father abandons his family when he's three, and then he leads a life of delinquency and transience, until he finds his father and gets into a bar brawl with him.
3/ Leader of the Pack by the Shangri-Las
The girl's boyfriend dies. He gets killed in front of her in a motorcycle accident. You get the picture? Yes, we see. But she met him at a candy store, so like, how tragic could this song feel?
4/ Please, Mr. Postman by The Marvelettes
Okay, so this isn't that sad a tale, but it's kind of sad--I mean, the girl's boyfriend is far away and she hasn't heard from in a long time and doesn't know whether he's coming back, and she's begging the postman to check again. C'mon, that would make you cry in a movie. But not in this song--in this song it makes you hum and tap the steering wheel.
5/ It's My Party by Lesley Gore
I know we all know this one, but it's about a girl whose friend steals her boyfriend at her birthday party. And yet I feel the strong urge to add "Bu-bu-be-do!" to the end of the chorus.
I tried to find more modern whiny emo songs to compare to each of these songs based on them having similar lyrical content, but I got bored. Also, I don't know of any songs written in the last ten years about a boy who got given an unfortunate name by his father. Do you? I'd sure love to hear it.