This is based on opinion. Please don't list it on a work's trope example list.
Nightmare Fuel / They Might Be Giants
Hide Away Folk Family, especially the coda, which culminates in something not unlike Courage suffering from catatonic shock.
"Rabid Child" from their first album is quite haunting. It starts off with a distorted and warbling voice that says "Lord, please don't take me away..." It also has a music video, which except for one clip, has NEVER been released to the public. Said clip has dark and ominous lighting and a disjointed vibe. The mystery surrounding the video certainly doesn't help with the creepy factor either.
Oh, you know that song "The Statue Got Me High"? The one with the statue that just makes people burst into flames and die? The song mentions it's being displayed publicly. And now, the weather.
To add to that, try not to scare yourself with John Linnell's intense stare. Who says statues can't move. And sing.
"Turtle Songs Of North America," a free download from one of their old sites, consists entirely of weird noises and John Linnell speaking in a creepily calm southern accent about several imagined North American turtles, including the Eastern Fighting Turtle, the Downy Tortuga, and the Mudflail.
"Replicant" from their 2013 album Nanobots. It's a slow jazzy song with some creepy electronic noises. The lyrics imply that the titular "replicant" has killed his human counterpart.
Replicant why do you lie on the ground, Shoveling handfuls of dirt on yourself?
The creepiness factor doubles when Linnell begins addressing the replicant like a son. And at the same time, it becomes clear that something very wrong is going on.
Replicant, someone is waiting outside He says you did something wrong to his friend Look at me when I'm talking to you What have you got there behind your back? I found this when I was cleaning your room I think you've got some explaining to do Whatever you did, we'll get through this Go out the back and I'll deal with the cops
"The Darlings Of Lumberland". If the demented woodwind section doesn't at least disturb you, John Flansburgh's demonic altered voice certainly will.
"Aaa," off "Glean" speeds through lines concerning everything from tinfoil-hat conspiracies and impending misfortune to distrust of surroundings and grievous bodily harm.
What's this button do? I wonder what's inside this ticking Package that's addressed to me, and how are sausages made And what am I made of? I'm gonna find out now
The early and obscure Dial-A-Song track, "Hi Honey I'm Home". Don't let the innocent-sounding title fool you. The song consists of Flansburgh depressingly singing "Hi, honey, I'm home" backed to a droning two-note synth loop and the sound of a car crashing.
It should be noted that the droning sounds exactly like a European-style emergency siren. Hell Is That Noise indeed.
The cold, synth-y "Am I Awake." It's about someone who's so trapped in the monotony of their daily routine that they've lost all sense of time, to the point that they can't even tell if they're awake!
"And when I close my eyes, it looks the same as when I open them again"
The brief track "Sleep" from Nanobots concerns a person who believes that when he goes to sleep, a doppelganger impersonates him.