Growing up I was obsessed with any and all Legend of Zelda games. I was also a child who was prone to massive anxiety and freaked out by anything remotely uncomfortable. This was problematic because as fun as Zelda games are...they can also be just as unsettling and creepy at times! These characters would creep me out and keep me from playing the game past sun down! Seems silly now, but I haven't tried to play Zelda at night in awhile so maybe these still hold true!
By the way no Tingle in this list...I know he's creepy but that's basically cheating to have him in this.
Grog (Multiple Games)
The very first time I entered Kakariko village it was at night. This was the days before fast internet and walkthroughs were expensive so I had no idea I needed to wait until day to progress the game. If I remember right I was so horrified of those little skull things that attack you in the overworld I was just happy they weren't chasing me anymore!
So here I am in a new area and the entire place looks empty. Looking back I blame N64's lack of draw distance for my initial fear of Grog. A kid sees a big tree in the middle of a big village and he immediately wants to roll into it! So I'm running at this thing and all the sudden this creepy ass looking dude is sitting under it and his head immediately darts up when I'm in range.
I remember thinking he was a boss or something and I hightailed my Link clear across the area! I'm doing everything I can to try and escape this guy! This includes running to the back of the level...seeing the graveyard and Dampe and immediately turning right back around. I start trying every door and quickly realize that was a terrible mistake (more on that in a bit)..and I'm stuck.
I really really don't want to talk to that guy, but the sun isn't coming up, and he doesn't seem to be attacking me, so I approach. I talk to him and immediately I'm sucked into...
"People are disgusting. My parents are disgusting. You must be disgusting too!"
11 year old me is like "WTF" and that wasn't even a phrase yet. It helped though because you slowly learn Grog is more of a sympathetic character than his appearance would lead you to believe. Plus he's a lot cooler in Majora's mask...he has a mohawk and everything!
Unfortunately those who do not remember how Ocarina Of Time progresses Grog gets lost in the "Lost Woods" seven years after you meet him and apparently becomes a Stalfos...likely one that you killed on your way to the Forest Temple.
Skulltula Family (Multiple Games)
Of course when I'm already shook up by Grog and looking for an exit I go into this house. You walk in a room that looks scary enough and then all the sudden a half human spider monster descends from the ceiling!
I'll admit I tried to end it then and there! The messed up part is the game actually lets you hurt them! You can't kill them...but rather stun them and they let out this disturbingly muffled human shriek that I can still remember to this day. After I got over my trauma I learned that these people too are not bad guys...well totally anyway.
The "Fabulously Rich" family were turned into Skulltula's due to their greed and would only be cured if all the golden skulltula's in the world died. Kind of a messed up curse considering they can't even leave their house!
Once again I eventually conquered my fear after my cousin informed me helping them gives me a larger wallet. Before the internet we had older cousins to help us get through video games.
??? (Multiple Games)
I would imagine this would be the first guy on everyone's mind when they saw the title of this post. Spanning across 3 Zelda titles (Majoras Mask, Oracle of Ages, Skyward Sword), ??? has had the same role in each game. He's a man who lives in a toilet, his hand is the only thing visible, and he desperately needs paper. Is he writing a novel? Maybe he has a lot of wiping to do since he's getting it both ways...we will likely never know.
What we do know is that Shigeru Miyamoto created the character due to Japanese horror stories he read as a kid. Supposedly these stories contained monsters who would pull people through toilets as they sat on them. Sounds like Japan right?
Truth be told this wasn't something that bothered me as a kid. I actually thought it was hilarious there was a dude living in a toilet. Then I got older and the whole logic of the thing really creeped me out.
Kamaro (Majora's Mask)
You remember this guy right? You see him on the outside of the city dancing only in the very late hours of the evening. Out of all the characters who die in Majora's Mask, he's probably the funniest, but the combination of his weird ass dance, and the fact that he literally gives you his rotting head to wear as a mask kind of send it over the top. PLUS THAT MUSIC....ugh still gives me chills.
The Happy Mask Salesman (Multiple Games)
I think the Happy Mask Salesman didn't really get creepy until the whole "Ben" creepy pasta, but it doesn't dismiss the fact that he is kind of the creepiest guy in the game. For starters he's the only character besides Link and Epona who is capable of traveling between universes. Crazier still, he seems to be able to do so at will. In a sense the sales man is the all powerful figure in this universe, yet uses none of his power to affect the tragedy happening within either world.
Think about it. This guy had Majora's mask during Ganondorf's seven year reign...and did nothing. Why?! What larger role does he play in the Zelda universe? I would love to find out one day.