What are the most upbeat songs with kind of depressing lyrics?

My boyfriend said he thought about me when we listen to Saturday Night by the Misfits. I'm like.... do you want to murder me?...

The lyrics always sounded very murdery to me. I think they did an amazing job of making it sound romantic but bf read through the lyrics after that and hugged me when I got home and said he definitely didn't want to murder me.

Edit: Ok this one is purely personal but I just got done with work and it came out on the playlist, Achilles Come Down by Gangs of Youth.

I learned this song from my daughter. I let her control the music when we'd drive to school and back but I immediately loved this song because unlike me, she has an amazing voice. This is one I only ever heard underneath her crystalline soprano while she sang along.

It was always so beautiful that I didn't focus on the song so much as her. She made a haunting, sad song a beautiful, pleasant memory for me because now she's had her license for a while, she's doing her thing being an ambitious senior. I don't get to listen to her sing anymore between my work and her school/social schedule.

I miss the days when I stayed up after a 12 hour shift to take her to school because I miss listening to her sing. I brain was fuzzy and that morning sun seared my eyeballs but I cherish every morning now because I don't have many left. I acutally miss everything about my kids needing me now that one has been independent for quite a few years and the other two are almost independent. I'm listening right now and all I can hear is her voice.

Fuck that shit hits hard. Im going to be an empty nester soon. Fucking FUCK. Fuck does it hit hard. I should be proud. I am! Jesus am I. I don't know how I was blessed with these people, bio and adopted, that's how vlessed I am, but I don't want to look the gift horse in the mouth. Fucking wow, am I proud. But really I'm sad, too.

/soliloquy

Pumped up kicks

Under the bridge Red Hot Chilli Peppers

Came here to post pumped up kicks

Hey Jealousy by The Gin Blossoms comes to mind.

Rock-a-bye, baby

On the tree top

When the wind blows

The cradle will rock

When the bough breaks

The cradle will fall

And down will come baby

Cradle and all

We sing that shit to literal babies, what the fuck is wrong with us?

Pumped up kicks fits this for me.

what do you mean? isn't that just about the modern american dream?
- Shooting up your school? What schools did you go to?
- It's about pumping up your shoes before b ball at recess.

Foster the People - Pumped Up Kicks

My (American) kids love this song. :D
This one immediately came to mind. They have a lot more good songs too.
That was my first thought.
Houdini is no slouch either

99 Luftballons is upbeat and fun, and about some balloons inadvertently kicking off a cataclysmic war that leaves the world in ruins.

It's about the cold war paranoia. Sound is all synth pop upbeat, though.
The English version is called "99 Red Balloons".
Damn, I gotta go read those lyrics.
The balloons were a metaphor for the mushroom clouds from the nukes going off
- In my opinion, the lyrics tell a pretty straightforward story, no real need for metaphor
  Someone releases a bunch of balloons into the sky, they get mistaken for enemy aircraft/missiles, and set off a war.
  If you get more out of it with your interpretation, more power to you, but it feels like a bit of an unnecessary stretch though.

90% of ska/ska punk music is like this. A few examples:

"The Science of Selling Yourself Short" - Less Than Jake

"Beer" - Reel Big Fish

"Struggler" and "I Don't Love You Anymore" - Bomb the Music Industry!

"The Last Bell I Will Ever Hear", "1-800-ALARM-ME" and "Last on my List" - The Arrogant Sons of Bitches

"Ska Dream" and "Checkerboard Ashtray" - Jeff Rosenstock

"A Better Place, a Better Time" and "As the Footsteps Die Out Forever" - Streetlight Manifesto

Nearly Everything by Reel Big Fish. It's all fun ska and mostly about social anxiety, broken hearts, and substance abuse. I love them.
- I'll have to listen to that one! "I Know You Too Well to Like You Anymore" fits the bill as well. A very ugly fight between a couple who hate each other but can't live without one another.
Absolutely this.

You are my sunshine

The other night dear As I lay sleeping I dreamed I held you in my arms But when I woke up I was mistaken so I held my head and I cried You are my sunshine My ONLY sunshine

It doesn't get any better from there

Edit: I will never understand how to format things the way I want them to sorry

Semi-Charmed Life by Third Eye Blind is the usual one I see brought up.

Push by Matchbox 20 and Possum Kingdom by Toadies are arguable ones.

Also, Richard Cheese covers a lot of raunchy and dark stuff in a vegas lounge singer style. Rape Me sung in a cheesy upbeat tone is a trip.

I wouldn't say Push is up-beat. Or at least the fact that the refrain is so openly negative undercuts that vibe with immediacy, in comparison with Semi-Charmed Life, for example, where you don't realize it's all horrible unless you pay close attention.
I fucking love Richard Cheese, especially his cover of Closer.
- Omg, this is a true pickmeup 🤣🤣
  The intro sounds like it's some Blues Brothers number and then... I want to violate you
- Check out his close friend and confidant, Johnny Aloha!
I wouldn't say Possum Kingdom is upbeat even in sound.
- Agreed. Maybe if it were set to the tune of Mr. Bluesky...
  Please tell us guy
  \ Please tell us why
  \ You showed us your dark secret
  \ Seeecret
I do love the Richard Cheese cover of Down With The Sickness.

Fast Car

Pumped Up Kicks

Flowers on the Wall

Hey Ya by Outkast.

Also pretty much everything I have ever heard by Steely Dan.

Hey Ya is an excellent example.
Steely Dan seems more low key. And he hates on my alma mater lol. And he acted like kind of a dick when I saw him live. But I do love his sound, like warm tea with honey and a lil splash of bourbon.
- Ok, maybe just the bourbon, honey optional.

Semi-charmed Life

Every Stromae's songs.
It's always funny to see non-french-speaking people being so hyped by Stromae's songs, like they think it's joyful af and all... While his songs lyrics are litterally about :

a man who drinks and dances a lot in order to forget his shitty life ( Alors on danse )
a song about his father who was killed during Rwanda's genocide ( Papaoutai )
other songs about suicide, cancer, breakups, addictions, depression etc... But always with an upbeat melody !

I don't speak a lick of French (I know enough Spanish to recognize some words if they are slightly similar, but that's it) but still enjoy Stromae, although I've never found his music to be upbeat. I think, especially in Papaoutai, you can hear the struggle and sadness in the tone of the song and in his voice.

Hey Ya - Outkast

Y'all don't wanna hear me, you just wanna dance...
Nice, I scrolled the comments hoping I'd find this one
Ghettomusick - Outcast
It is a really sharp critique of the rap industry at the time.

Pumped up kicks by foster the people

Happier - by Bastille and Marshmello. It might depend on the listener tho.

Aint it fun - Paramore

Honestly, i don't like that a lot of radio music is so sad. I have to look to real oldies to find a happy song.

People forget that Today by The Smashing Pumpkins is literally about suicide.

But it's about the euphoria one may experience after deciding to go through with it. Ya^a^y^y
/s
PS, I have witnessed the euphoria, but I didn't recognize it for what it was at the time. They were calling to say goodbye. Fuck, that still gets to me.
I wouldn't call the smashing pumpkins upbeat. Some are up tempo, .maybe, but upbeat is not their style. Their biggest album was titled Mellon Collie and the infinite sadness. Not exactly cheerful stuff.
- I’ve heard the song used in those compilations of sporting events you see on TV before said sporting event, to celebrate a athlete.

Jonathan Coulton has a bunch of these. "I Feel Fantastic" "Betty and Me" "Blue Sunny Day" "Shop Vac" "Chiron Beta Prime" "Future Soon" off the top of my head. "Skullcrusher Mountain" and "Re: Your Brains" to a lesser degree.

I love Future Soon.
shop vac has been playing in my head on loop for a few weeks and it's been more than a decade since i last heard it. it's so depressing.

Semi-Charmed Life is the first thing that always comes to my mind

Rockin in the Free World by Neil Young

Good point. Born in the USA and Fortunate Son would probably fit in here as well.
- Other songs frequently misunderstood by people of a certain political party

Born in the USA

Someone's boat was blasting that at the 4th of July on the water. My brother in Christ, I understood the lyrics back in 1984. It's a jammin' tune, but damn.

Brown Sugar

A lot of that album was pretty subversive but hidden behind upbeat rock. The olds didn't realize what the kids were listening to because they just heard pop rock.

hey ya -- Outkast It's about relationships that aren't working out, but you still stay together.

" thank God for Mom and Dad / for sticking two together cause we don't know how"

Then later

" are we so in denial when we know we're not happy here? / y'all don't want to hear me, y'all just want to dance"

Zero 7 - Waiting to die

https://youtu.be/ge1_eVMO-mU

Snowpix mentioned lots of ska/ska punk I gotta agree, my pick is The Aquabats - chemical bomb

https://youtu.be/Y3fXdcHQY4o

Maybe a bit of a stretch but just running with the musical tone doesn't match the lyrics Ben Folds - bitches ain't shit cover

https://youtu.be/gjFRy8jQ_0U

pretty much anything by third eye blind

HEALTH - everything from the band is banger after banger but with lyrics that'll leave you feeling a certain type of sad

Ring around the rosey

And

Fuzzy wuzzy was a bear

My Worst Enemy - Lit

Man, who is probably an alcoholic, wakes up the next day from a bender to find his girlfriend has left him.

So I listened to some of Lit's new stuff, they went full religious man. Bummed me out.
Stroke 9 on the other hand are fucking amazing and I love nearly all their tracks, their latest two albums are sick, Lake got me back into them, then went back to all their stuff I missed. Here's a screenshot of my ratings :)

The Motown hit Keep Me Hanging On by the Supremes is the classic example of this.

It was even recognized for its pathos and turned into a sadder slow version by psychedelic band Vanilla Fudge

This is probably a controversial opinion, but Ive always felt a little bad for the guy this song is about.
I think it's unfair for her to say he doesn't care a thing about her. He obviously does. If he didn't he wouldn't want her to still be a part of his life.
This song is just about two people who want different things out of their relationship, and the singer is just unable to accept it.
She has the ability to cut him out of her life if that's what she really wants, same as he does. She should cut herself free if it's too painful for her to be his friend.
- I feel that. Maybe this song is her way of cutting herself free? Or by telling him to make a decision, she's giving him more autonomy than if she just left. Like she's saying, "Look, we need to commit to a decision, no more up and down, which way would you have it?"

Vamos a la playa - super catchy totally 80s pop song that was everywhere in amusement parks ..... and it's about nuclear hellscape.

Sad lyrics and fast tempo :
Kazim Koyuncu - Narino
Bagpipe song with the lyrics "I lost my sanity", "I sat down and cried", and "I wish someone knew my pain" especially. Can find longer versions on youtube.

French Gal - Poupèe de cire
Lyrics are about feeling more like a doll than human. TRIGGER WARNING FOR FRENCH LANGUAGE

Kazim Koyuncu - Fadime
Kemençe song with lyrics along same lines. Takes a bit before beat changes.

Sad lyrics and happy music/tone :
Danny Gonzales - Downhill
Song argues with a young adult on how rest of their life will suck.

Istanbul12 Orkestrasi - Bile Bile
Song about being unable to accept rejection.

Ayase/YAOSABI - Into the night
I am 70% sure "upbeat sounding song about suicide" is a genre in Japanese music.

Mmmm Bop

No that song doesn't exist in this timeline

Like half of Fall Out Boy's discography. "Hum Hallelujah" gets a special mention for literally being about a suicide attempt. Also "Dance In the Dark" by Lady Gaga, "Stomach Vs Heart" and "Humor of the Situation" by Barenaked Ladies ("Angry People" as well), "Slip Slidin Away" by Paul Simon, "When I Come Around" by Green Day...suffice it to say, I enjoy this trope a lot :P

pumped up kicks

Love - Forever Changes. The whole album.

https://youtube.com/playlist?list=OLAK5uy_lIfiGGgw0nJ6H3UcVvp1UbFhwr0LGPiBE

The Macarena I'd about a woman cheating on her BF getting drafted into the military with 2 other guys

Which is pretty intense for a song they taught to kids in grade school

No Rain by Blind Melon... literally a song about deep depression with upbeat music

He committed suicide not long after that song hit the charts.
Looking at wikipedia it was longer than I thought
- He ODed. So he did kind of kill himself, but it wasn't a suicide.

Timothy by The Buoys is a very happy song about men trapped in a mine collapse cannibalizing each other to survive.

Radiohead - No Surprises

Talking Heads - Life During Wartime and Once in a Lifetime spring to mind.

It's probably easier to list the Talking Heads songs that are not upbeat and depressing.

Bad Moon Rising by Creedence.

It's about the apocalypse, but you wouldn't know it from how upbeat it is.

If they didn't use this song in True Blood or just about any other campy Mississippi delta monster/ slasher film, then they done messed up.
I could only make it through the first season of True Blood, having read all the books that were available at the time. I actually learned about the book series and the show from a SDCC panel (we wanted good seats for the panel immediately after the True Blood one). Watching as Charlaine Harris's fans lost their everloving minds got me all curious.
Ah, rhe bathroom song.

Glory Days by Bruce Springsteen. It's about realizing that you've peaked and your best days are behind you.

This song hits different now that I have some mileage on me.
We'll time slips away and leaves you with nothing, mister, but boring stories offfffff glory days
I can watch my nephew checking out in real time if we tell too many back in the day stories at family dinners.
Also, my favorite sports bar used to be Glory Days.

When You Die - MGMT

El Fusilado - Chumbawumba. A happy clappy sunshiney recounting of the life and times of one Wenceslao Moguel, a soldier of Pancho Villa's who was captured, executed by firing squad, and lived to tell the tale. Short version: He got knocked down, but he got up again.
Scarborough Fair - Folk; often associated with Simon and Garfunkel. I'm stretching the definition of "upbeat" here, but it baffles me that this is counted by anyone as a love song. It's a song about two ex-lovers expressing how much they hate each other by assigning each other impossible tasks as conditions for taking them back. He says "tell her I'll take her back if she sews me a shirt with no seams, washes it in a dry well and hangs it to dry on a vine with no thorns." She says "O RLY? Well you tell him that if he finds an acre of land between the ocean and the beach, sews it all with one seed and reaps it with a leather scythe, I'll take him back. And I'll even make him his damn shirt." It's a bitter song.
Another Day In Paradise - Phil Collins. Again I'm stretching the definition of "upbeat," it's slow in tempo, kind of heavy, but it has that big sexy hook, manages to feel kind of breezy, it feels designed for first dances at wedding receptions, and the refrain is "It's just another day for you and me in paradise." It feels like a competitor to Fields of Gold by Sting. It's not! The verses are about the humanity crushing power of abject poverty.

Chumbawamba are great, especially that album.

I always found The Scientist by Coldplay to be a pretty upbeat song about the death of a loved one. And Viva la Vida upbeat, and all about the fall from grace.

Pick any Smiths song

"I was happy in the haze of a drunken hour, but Heaven knows I'm miserable now"
🎶 if a ten-ton truck 🌈 🎤 killed the both of us 🎶

Pumped Up Kicks - Foster the People.

Lots of mentions of The Boss, but not those other cheery Jerseyites. Bon Jovi with “Livin’ on a Prayer.”

I don't like Mondays by boomtown rats

https://open.spotify.com/track/7JFoeg0arawADjGcz9gBnq

Quite a chill and happy song about a school shooting

An actual school shooting and I think the shooter thanked Bob Geldof for making her more famous

Nothing but Flowers by Talking Heads is a cheerful song about post-apocalyptic life.

Hey Ya

Mack the Knife https://www.youtube.com/watch?v=fZ0OOHLWo4w

Has anybody mentioned Joy Division yet?

You are my sunshine (The Dead South do an excellent job illustrating how dark the song really is)

I'll Fly Away also fits that.
Love The Dead South, their vaguely ominous horror take on folk is amazing! Johnny Cash also does a wonderfully depressing version of the song

Walking on broken glass - Annie Lennox

Bullet by Hollywood undead.

Singing about killing himself in a super upbeat song, even has kids at the end going "I wish that I could fly, way up in the sky", the part where he was singing about jumping off a skyscraper.

Club America by The Cure

I think I have the best answer here: Gwar - Rock N Roll Never Felt So Good

Lyrics

David Bowie - Five Years Tennessee Ernie Ford - 16 Tons Iron Maiden - 2 Minutes to Midnight

And about half of Pink's oeuvre.

I think Enola Gay by Orchestral Manoeuvres In The Dark is a perfect example.

It sounds upbeat and fun but it's about the atomic bomb dropped on Hiroshima.

Some of the lyrics are incredibly powerful and I still get chills when I hear it.

Flagpole Sitta - Harvey Danger?

This was one I would absolutely belt out in the car when I was so over the DC life.
I'm not sick, but I'm not well

The only 2 songs I could think of, Pumped Up Kicks, and 99 Luftballons/99 Red Balloons were already brought up. So I had to think of some different songs. And I can't. Looked through a bunch of songs on my phone and back of some of my CD cases and I can't think of any right now.

Closest I can think of was just a video of someone reacting to the Japanese vocaloid song 「ごめんねごめんね」 ( I'm sorry I'm sorry )by Kikuo and not knowing what the song meant until looking up the lyrics. Even then, that's not a very upbeat song.

Edit:

I thought about "Belong" by R.E.M., but I would say it's near upbeat but not quite there. Also, the lyrics are more cryptic and confusing to dissect than depressing in my opinion.

Edit 2:

Wouldn't say it's quite upbeat either, but Mighty K.C. from For Squirrels as well. Not quite upbeat but definitely depressing lyrics considering it's about death.

Hard Times - Paramore first thing I thought of

I Am A Rock by Simon and Garfunkel

    
A winter's day  
In a deep and dark December

I am alone  
Gazing from my window to the streets below  
On a freshly fallen silent shroud of snow
I am a rock I am an island

I've built walls
A fortress deep and mighty
That none may penetrate
I have no need of friendship, friendship causes pain
It's laughter and it's loving I disdain
I am a rock I am an island

Don't talk of love
Well I've heard the word before
It's sleeping in my memory
I won't disturb the slumber of feelings that have died
If I never loved I never would have cried
I am a rock I am an island

I have my books
And my poetry to protect me
I am shielded in my armor
Hiding in my room safe within my womb
I touch no one and no one touches me
I am a rock I am an island

And a rock feels no pain
And an island never cries

In that vein, I guess, "The Sound of Silence" by Simon and Garfunkel also deserves a mention, even if it's up for interpretation how depressing the lyrics by themselves are.
But the first line in the song is "Hello darkness, my old friend / I've come to talk with you again." and there is a cover version by the metal band Disturbed, which has no shame to really lean into that sort of vibe.
And yeah, after having heard the Disturbed version, listening to the original certainly feels like there is a massive disconnect between how sad the song perhaps should be and how upbeat the original is.
- In what world is The Sound of Silence considered upbeat

Little talks - of monsters and men
It sounds very chill and upbeat but it’s about the loss of a loved one

I had a period where I could not listen to this one. It hit too hard.

The Science of Selling Yourself Short by Less Than Jake

"I could be an expert on codependency, I could write the best book on underage tragedy. I've been spendin' my time at the local liquor store, I've been sleeping nightly on my best friend's kitchen floor. And so I sit and wait and wonder, "does anyone one else feel like me?" I'm so overdosed on apathy and burned out on sympathy"
Yeah, I think the song checks out lol

Flo by Smash Mouth

Fish Yu Mang is a great album, and I'll never miss an opportunity to give it love. Definitely the depressed thoughts of a dude who suffers from crippling alcoholism, but somehow manages to sound fun and upbeat the whole time.
- That's my take as well, I started giving it more attention only recently and there are many gems in it. Padrino is one of my all time favourites of the genre

Plenty of ABBA songs... Maybe Chiquitita?

It's a little more than kind of depressing but Bullet by Hollywood Undead comes to mind.

I wish that I could fly!

Last Kiss by Wayne Cochran. You kids probably remember the Pearl Jam version, which was a bit more subdued. But the 1964 hit by J. Frank Wilson and the Cavaliers is very upbeat and cheerful sounding. It’s about a boy who gets his girlfriend killed in a car accident while on a date and holding her as she dies. He’s consumed with guilt and can only think about dying so he can see her again in heaven.

Class A Team

Billy Idol - Dancing with Myself Loneliness masked as liberation.

Bulletproof - La Roux Emotional numbness disguised as empowerment

Some Linkin Park songs (Bleed it out, Up from the Bottom, etc.)

There's so many such songs...

Not entirely upbeat, but people always play Linger by the Cranberries like it’s a love song. Most definitely isn’t.

Mmmmbop

A good chunk of They Might Be Giants' discography.

Homeless Bleak Despair is about what's in the title.

Don't Let's Start "Everybody dies frustrated and sad and that is beautiful"

My Man is about being paralyzed.

That just scratches the surface.

I know that there are probably a lot that I'm forgetting but here are the ones I remember:

No more crying by Sound Holic (lyrics)

Border of my life by Sound Holic (lyrics)

THE END by A-One

IT IS SO by A-One

U.N. Owen Was Her? by A-One

For happy/energetic sounding but sad anime-style touhou songs there is also Stack, Stack, and Stack

No Sunlight - Death Cab for Cutie

    
When I was young
Lying in the grass
I felt so safe
In a warming bath
Of sunlight, of sunlight
The vast open sky
Could do no harm
Like an embrace
Of a mother's arms
In sunlight, in sunlight
In sunlight, in sunlight
With every year
That came to pass
More clouds appeared
'Til the sky went black
And there was no sunlight, no sunlight
And there was no sunlight, no sunlight anymore
And it disappeared at the same speed
As the idealistic things I believed
When the optimist died inside of me
No sunlight, no sunlight
No sunlight, no sunlight
It disappeared at the same speed
As the idealistic things I believed
When the optimist died inside of me
No sunlight, no sunlight
No sunlight, no sunlight
No sunlight, no sunlight
No sunlight, no sunlight
No sunlight anymore

Neutron Dance by the Pointer Sisters

Really? I'll have to check out the lyrics now. Such an 80s staple that I think I just sang along and never really processed the words.
- The title of the song is a reference to nuclear war.
- I don't want to take it anymore I'll just stay here locked behind the door Just no time to stop and get away 'Cause I work so hard to make it every day
  Whoo-ooh Whoo-ooh
  There's no money falling from the sky 'Cause a man took my heart and robbed me blind Someone stole my brand new Chevrolet And the rent is due, I got no place to stay
  Whoo-ooh Whoo-ooh
  And it's hard to say Just how some things never change And it's hard to find Any strength to draw the line Oh, I'm just burning doin' the neutron dance I'm just burning doin' the neutron dance
  Industry don't pay a price that's fair All the common people breathing filthy air (Lord, have mercy) Roof caved in on all the simple dreams And to get ahead your heart starts pumping schemes
  Edit- but the vibe of the song is so upbeat you’d never know

Almost anything by Tom Lehrer.

Bullet by Hollywood undead

Living La Vida Loca and Macerena are both pretty dark.

The fact that macarena has been played at nearly every wedding I've been to is diabolical.

Surprised that people haven't mentioned Yoru ni Kakeru (Racing into the Night) by Yoasobi. It's a Japanese song about depression and commiting suicide.

Specifically, it follows a guy who falls in love with a depressed and suicidal girl. Over time, the guy himself becomes depressed and tired of life and they both decide to commit suicide together.

^ Scrolled all the way down looking for this one.

Eleanor Rigby by The Beatles
Some Nights by Fun (and the music video really reinforces it)
I Wanna Get Better by Bleachers
a bunch of different songs by P!nk
Weird Al's presidential debate autotune songs ("Bad Hombres, Nasty Women" from 2016, "WE'RE ALL DOOMED" from 2020, and "Deja Vu (But Worse)" from 2024)

I have to disagree with Elanor Rigby. Yes it's a quick tempo, but the E minor key makes it very bleak even without the lyrics. And I may be wrong but it's also an overall pretty bleak song for Paul's typical compositions. So it's kind of always stood out to me.
I do love it very much though.
I would submit And Your Bird Can Sing as an upbeat melancholy song off Revolver.
- I have to disagree with Elanor Rigby. Yes it's a quick tempo, but the E minor key makes it very bleak even without the lyrics.
  Those strings go hard, though.
  I guess it depends on your definition of "upbeat." It could mean cheerful and happy, or it could mean lively and fast-paced.
  I don't think being in a minor key is necessarily enough to invalidate the first definition, let alone the second. I'm not gonna link it because fuck R*edit, but there's a thread there with plenty of examples of upbeat minor-key songs, including Uptown Funk, the Inspector Gadget theme, Get Lucky, Tunak Tunak Tun, Livin' LA Vida Loca, Get the Party Started, etc.

for some reason there's a bunch of upbeat sounding Japanese songs that are actually disturbing if you look into the lyrics (for example racing into the night)

Bad Apple

Mark Knopfler has quite a few. Postcards from Paraguay. Quality Shoe. Romeo and Juliet. Boom Like That. It's a thing with him - contrasting the music with the theme.

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.

It'd be hard for a song with a title like "Pompeii" to be anything but dark, LOL

Porcupine Tree - Blackest Eyes

Mew - She came Home for Christmas

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

on melancholy hill - gorillaz

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

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

You’re Gorgeous

Fuck You - The Used

A lot of Elliott Smith songs.

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.

I mentioned Bruce & CCR in another nested comment a little before you posted, but I don't think I'm familiar with this Stevie song. I'll go check it out.

Rise Against - Tragedy + Time

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

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

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®

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.

Checked out Apoptygma Beezerk's cover?

Twisting In The Wind - David Byrne

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

most of the after laughter album by paramore

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

Boys of Summer is about toxic obsession.

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.

Blackest Eyes by Porcupine Tree

Passion Pit - Sleepyhead

The Muffin Song

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

That's like Paul Simon's entire schtick. Alongside downbeat songs with uplifting lyrics.

I always thought Free Four by Pink Floyd fit that category well.

The entirety of hissing fauna are you the destroyer by of Montreal

The Antlers - Bear https://www.youtube.com/watch?v=dnHCQe-Y0nw

May I introduce you to The Smiths. Rusholme Ruffians and There is a Light That Never Goes Out are great examples, but really it describes most of their catalogue.

Ye, Renew the Plaintiff by Of Montreal

Ruru's suicide stream ? Would that one count ? Damn it's like all the songs flew out of my brain the moment I read this question ahahahh

Greenskeepers - Lotion https://www.youtube.com/watch?v=Jm86I_kezVY

Just Ain't Gonna Work Out - Mayer Hawthorne