TL;DR - saw a man under a streetlight in the dessert while driving at night, drove by again forty minutes later and he was still there. Not sure if drunk, person pulling a prank, or what.
So this isn't "piss your pants scary," but it was sure as hell unsettling at the time, and I've been waiting for a time to share it so here goes.
About eight years ago now, two nights before Halloween (which probably explains more why this freaked me out, and could explain what actually happened), my parents and I were driving to a local store to pick up some pumpkins. It was fairly dark by this point in the day, as we had waited for my dad to get home from work, and he typically works pretty late. I remember I was driving, which made the whole thing a bit more surreal in the end.
Where my parents live is on the outskirts of town, pressed up against the foothills of the neighboring mountains. It's high desert country, so once you go towards the hills you immediately hit sagebrush, open desert, and at night, plenty of unlit, uninhabited darkness. The route we took to the store ran up near the foothills, basically at the edges of the housing developments. This means that there was some housing, some streetlights, but also with fair stretches of land without houses built yet, though developments were still going in fairly quickly. This resulted in some paved roads that branched off from the main drag, leading nowhere but towards desert, some of them with a streetlight standing at the intersection, illuminating not much of anything at all. Back when I was an infant, if we were out driving at night, I would howl and scream about not going this way, as I was afraid of the dark, and this was the darkest place I could imagine.
Anyways, we went driving towards the store, taking this dark road to get there as it was faster than dipping down into town and hitting streetlights, stop signs, the usual hustle bustle. I knew to take this road fairly slow, as we got plenty of deer in the area wandering down from the hills, and you don't want to come around a bend too fast with one of those things standing in the middle of the road. I remember very clearly scanning the edges of the road, high beams blasting, focusing harder than normal so as not to miss any details. This is why I think I saw it, and why I think it startled me so badly.
As we were coming around a long curve, edging towards one of those developments that hadn't been completed yet, replete with road to nowhere and streetlight for nothing, I glanced over to one of the empty roads. I remember not registering anything until about a second before passing the street, but as we came abreast, catching sight of a man, standing in the middle of the empty street directly below a streetlight. I only saw him for a second, maybe two before we passed him, but I remember seeing in that moment very clearly that he was dressed entirely in rags, his hair was long and matted, and he was swaying where he stood. I remember jumping when I saw him, but then we were past and I had to keep focusing on the road.
I remember rationalizing it at the time. The guy was probably a homeless man. The swaying was because he was drunk. He was out near the desert because no one would bother him there. What I'd seen wasn't that much of a big deal, and I should just let it go. Plus, it was almost Halloween, and if the guy wasn't drunk, wasn't homeless, it was probably some jackass in a costume out and about a bit early. I let it go.
We were at the store for a good forty minutes, picking out pumpkins, getting those stupid little pumpkin carving kits, picking up some other groceries while my parents remembered item after item after item they needed and the trip dragged on and on. By the time we were done I'd entirely put the man under the streetlight out of my head, at least insofar as I wasn't jittery anymore. I'd rationalized the incident, and as we got in the car to drive home with our pumpkins and other odds and ends, I didn't think anything of it as I took the familiar route down the dark desert road.
As we started getting closer to that bend though, I started being curious again, thinking about what I'd seen. I knew there was no way it was anything supernatural, since that shit doesn't happen. I was more curious where the guy had come from, why he'd been standing under the streetlight, where he was headed. It was nearly November, remember, and the nights were cold and long, and most of the city's homeless stayed closer to downtown where they could find shelter and marginally more warmth. So I didn't think anything of it as we rounded the corner, coming abreast of the side street to nowhere once again. I looked off to the side, thinking about what I'd seen earlier.
He was still there. Standing in the exact same spot, swaying in the exact same way, lit in stark contrast by the light directly above him, outlined against the empty street and the desert beyond. Forty minutes later, and he was in the exact same spot. He hadn't moved an inch. The car zipped past him, and after another second we had rounded the bend, leaving him out of sight.
This might not be the creepiest thing in the world to some people, and this doesn't end with any sort of crap about escaped prisoners or crazy axe murderers (the escaped prisoner thing actually happened a year later). For all I know, all I saw was a drunk, homeless man dressed in rags, too wasted to move from the edge of the desert for almost an hour or longer. It could've been a scarecrow for all I know, or just some asshole playing a prank. Regardless, it spooked me the hell out, and now whenever I'm back visiting my parents, I always check that spot if I'm driving by at night.