I've been planning on replaying Y for a while now and finally got around to rescuing all of my Pokémon and depositing them in the pokebank. (I had four boxes worth since I transferred some from Heart Gold too.) As I was looking through my Pokémon, trying to find the ones I wanted to keep and finding out that I had a ton more shinies than I thought I did in the process, I noticed that some of the names were a little... weird. I named a Tirtogua "Kai" which is a name I later ended up giving to a Carracosta I bred for competitive battling. I named a Cranidos "Blue" and it just so happens a few years after I did, a certain dinosaur-themed movie came out with a Raptor named Blue. The creepiest one was a Pidgeot that I had named Piper. As some of you may know, about 6 months ago I got a little birdie irl that I named Piper. I agonized over coming up with a good name for her and Piper was a name I just happened to come across on a naming website, so it's a little weird that I would name a Pidgeot that. Especially considering that I always name my bird Pokémon after the birds I've owned. So yeah, funny little coincidences. I still can't believe that though. Next time I get a new pet, I'll just look through my Pokémon nicknames to find a name for it. Oh I also had two Pokémon next to each other named "Big" and "Ben" so that's kind of funny I guess, though that's probably just past-me trolling me, as usual.
I remember when I plugged in my SoulSilver (or was it FireRed?) I had a Togepi named something... ominous. Like Tartarus or Diablos or some other monstrously evil name. Togepi, of all things. Generally that's the weirdest name that comes to mind. Generally I stick with pop culture references that apply to me, and I try to make them fit, and that mostly precludes me from most silliness.
I don't think I've ever really named any of my Pokémon something weird, I think that the weirdest thing that I've named was a Dratini called Shadowlaser, but that isn't super weird to me...
Almost all of my Pokémon are named after puns/pop culture references For example, my Shiny Blacephalons (yes plural, I have two) are named Dippin Dots and Pennywise.
Umm... I was doing a Torchic giveaway and was naming them all weird things... And... Did you know the 3DS has a square smiley face emoji? Yeah. I just spammed that to the limit. It also has sun and cloud emojis. I simulated the sky with the name of another. I also named an entei magicarp Oh, and my blissey on my team is named Arceus. Just to confuse my opponents a little.
I named a Feraligtr, BIGJAW. I was seven, soul silver, didn't know you could use lower case, and was uncreative. I now have much cooler nicknames I could give one, like Riptide. But, I still name every Feraligtr I get BIGJAW purely for nostalgic purposes. I named a Mudsdale, Bruho. After a horse mi papa got for me, long ago. It's supposed to be spelled 'Brujo' since it's Spanish but I've always spelled it 'Bruho' since that's how I spelled it as a kid. I may correct the spelling in the future though. I named a Charizard Kraiser, for some reason, and one Kaiser (German for king).
I don't usually give my Pokémon super weird names. Though I did name the shiny Audino I caught in White "The Beast", because my brother and I thought It'd be funny to do so.