Tom Waits’ I Don’t Wanna Grow Up - its raucous tune makes it easy to take it as playful (and joyful) Peter-Pannism, but it you pay careful attention to the lyrics, it’s clear that it’s about suicidal ideation:
"A dragon lives forever, but not so little boys
Painted wings and giant strings make way for other toys"
My son is three years old … these lines are hitting me harder than they should 
Walk in the Park by Oh No, Oh My! - On the surface the poppiest of the pop. But it’s also got darkness, right there in front of your face!
There is a Light that Never Goes Out by the Smiths , maybe?
More Barenaked Ladies: I’ll Be That Girl. What. The fuck. Is going on in that song? The totally peppy chorus goes:
I’ll be that girl
you would be right over.
If I were a field,
you would be in clover.
If I were the sun,
you would be in shadow.
If I had a gun,
there’d be no tomorrow.
The rest of the song is no less weird and creepy. But you really have to listen to the lyrics to notice because it sounds so upbeat and cheerful.
Pretty much everything Sublime recorded…
I hate when they play this after a baseball game. I always wonder if anyone actually listened to the lyrics.
Bye Bye Love,
Bye Bye Happiness,
Hello loneliness,
I think that I could cry
Huh. I figured the first example would be Gilbert O’Sullivan’s “Alone Again, Naturally.” It always comes up in this context.
In a little while from now
If I’m not feeling any less sour
I promise myself to treat myself
And visit a nearby tower
And climbing to the top will throw myself off
“Maxwell’s Silver Hammer” by The Beatles
“Walk On The Wild Side” by Lou Reed
The Housemartins, and later incarnation The Beautiful South, made a career out of sweet, catchy tunes with acidic lyrics. Personally I think they shot themselves in the foot slightly, because the tunes were much better than the words, which seem slightly juvenile in hindsight. So now you get cosy radio stations like Magic FM playing things like “Song for Whoever” without any irony.
It wasn’t the first. It got slipped in at 13.
Tomorrow Belongs to Me from *Cabaret *is a good example:
The sun on the meadow is summery warm.
The stag in the forest runs free.
But gather together to greet the storm.
Tomorrow belongs to me.
It’s a beautiful ballad about taking the hope and promise of the future…
Sung by Nazis.
Death Cab for Cutie - No Sunlight.
Very catchy little track.
<pedant>giant rings… or possibly giant’s rings</pedant>
One of my favourites, my mother sang it to me as a little nipper. I sang it to my little boy… and it reminded me of her, and I missed her.
“Billy, Don’t Be A Hero.” Honest. A light, puffy sounding song which often gets dismissed as one of the worst songs of the 70s, with Billy’s embittered fiancee throwing away the letter describing Billy’s heroism under fire and how he sacrificed his life to go for reinforcements. His sacrifice was meaningless to his fiancee, who wanted Billy to keep a low profile and come home to marry her.
Lemon Tree by Will Holt, popularized by Peter, Paul, & Mary.
The song goes on to tell of a woman ripping a guy’s heart out.
“Happy Birthday.”
After a certain age, it’s not so happy.
Copacabana
The Housemartins’ words seem slightly juvenile in hidsight, or all of Paul Heatons’s stuff? The Housemartins I agree with - the Christian Marxism sounds a bit idealistic and naive. But the Beautiful South stuff is mostly about relationships and drinking, which still works, IMO. And it’s inevitable with this type of music that some people are going to take the music at face value without paying attention to the lyrics - it’s worth it when they one day get that “Aha!” moment and realize they’ve been humming along to lines like “Don’t shoot someone tomorrow that you can shoot today”.
Half Man Half Biscuit’s The Light at the End of the Tunnel (Is the Light of an Oncoming Train) has an upbeat tune and rhythm for a rather bitter song.