Ask Lemmy

A solid majority of Bastille's discography comes to mind, though not as outright depressing as Pumped Up Kicks or Youth of a Nation, most of their tracks tend to be very instrumentally upbeat and lively, with gorgeous vocals, but thematically darker lyrics / topics. Happier comes to mind as immediately fitting the prompt (and having enough radio play to be recognizable), but The Draw, Haunt, and Skulls also fit well (I'd also included their cover of City High's What Would You Do, also long as being a cover isn't a immediate disqualifier).

I feel like they're kind of slept on since they don't get a whole lot of radio play outside of a handful of songs, but all their other work is just so good. Personal top favorite artist, hands down.

Polish Dancing Cow song is upbeat and catchy but the lyrics are about a man struggling with his cocaine addiction.

Komm Süsser Tod from The End Of Evangelion.

I didn't see wake up boo by the boo radleys in here.

It's about suicide

Fuck You - The Used

Porcupine Tree - Blackest Eyes

Mew - She came Home for Christmas

on melancholy hill - gorillaz

Renai circulation, from the monogatari series. It's super cute but hidden inside is a cry for help.

You’re Gorgeous

A lot of Elliott Smith songs.

Neutron Dance by the Pointer Sisters

Charlie's Inferno is about an innocent man being tortured in Hell. It's a 50's style tune reminiscent of Mr Sandman.

Looks like we all forgot Bruce Springsteen’s Born in the USA.

Adding You Haven’t Done Nothin’ - Stevie Wonder’s bitch slap to Nixon, and CCR’s Fortunate Son.

Rise Against - Tragedy + Time

the mountain goats - no children https://www.youtube.com/watch?v=QS27S3mspjU

I'm Only Me When I'm With You by Taylor Swift. Granted, I have no experience with healthy relationships, but the relationship in that song sounds extremely unhealthy and codependent

Paul Thorn - Bull Mountain Bridge

Jonathan Coulton - Shop-Vac®

https://www.youtube.com/watch?v=Kkrb4h4weW4

I can probably put some more but this one has been on me for a while.

I always find it funny how upbeat the Cambodia version by Pulsedriver is. PTSD and dropping bombs on cambodia. What a topic for a dance tune.

Twisting In The Wind - David Byrne

In fact, the whole album's full of dark yet upbeat songs.

Straw Hat and Old Dirty Hank by Barenaked Ladies is about the real stalking of a Canadian celebrity by a mentally unstable man who thought she was in love with him.

https://www.upi.com/Archives/1981/12/31/A-love-sick-farmer-who-has-pursued-singer-Anne-Murray/8301378622800/

most of the after laughter album by paramore

also hey ya by outkast is often played at weddings while being about a relationship failing

Blackest Eyes by Porcupine Tree

Passion Pit - Sleepyhead

On the documentary 'shifty' they claimed that 'the land of make believe' by bucks fizz was written about Margaret Thatcher/Thatcherism. Really puts a depressing spin on it.

The Muffin Song

Boys of Summer is about toxic obsession.

Lots of great choices here - I'll throw in Moon Over Marin by Dead Kennedys.

Sounds like a bop, but is actually about the destruction of the environment.

Someone else mentioned this too, but if anyone is into Japanese songs: I think there are probably more songs (especially Vocaloid ones) with extremely messed-up (and convoluted) lyrics than those that do not... I don't think most of them are well-known outside anime/vocaloid circles though. Trying to think about the more "cute and depressing" ones I could find:

All Thats Left of Me is You by Vulfpeck

Little Foot Big Foot - Childish Gambino