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I've updated the list to include the number 10-1 spots. Some of the later entries may surprise you.

Soon, I'm going to be hosting a Mario-themed competition on Discord, and one of the challenges was going to be called "Quest in the Deep." It would've had teams go on Google and search for official images of weird or disturbing things that were either created or licensed by Nintendo themselves. But then I reread the list and was like, "Most of these can be found on the front page." So I scrapped it for being too easy. But I still wanna share the crazy things I found, so I'll be making a list going from those that are more innocent and well-known to those that are... well... neither, starting with...
14. Barefoot Yoshi
Yeah, this is one of the reasons I didn't make it a Google scavenger hunt. If you look up "barefoot Yoshi" nowadays, odds are you'll be met with some fetishy stuff, but what if I told you there's an activity book from 199-something that actually reveal's Yoshi's adorable paw?

Now, with his design changing throughout the years, I highly doubt this is accurate, but it's nice to see Nintendo having the balls to do that.
13. Various characters getting drunk
In a few games from the 90's, there are quite a few examples of characters getting completely wasted. The most appropriate example for this site is Bowser chugging down a bottle of champagne if he wins in Super Mario Kart. In one of the Wario Land games, there are also penguin enemies that'll throw beer mugs at Wario, turning him into, this is the official name, "Drunk Wario." Unsurprisingly, these were both Japan-only.
12. A Shy Guy without its mask
Now I'm kinda cheating with this one, but it's still fascinating. Shy Guys' main thing is that they always wear masks because they're shy guys. But there are a couple of times where the masks came off, and they didn't even have to lose a singing contest. The first one is from Mario Power Tennis. If Shy Guy wins, during the cutscene where he's collecting his trophy, he'll trip and lose his mask. When he gets up, his back is turned to the viewer, but Luigi is mortified at what he sees.

Okay, that image doesn't show fear, but it's the best I could find.
There's also a blink-and-you'll-miss-it scene in the Mario Movie. While the camera is speedrunning through the rave scene, you'll see a Shy Guy take off its mask to a few other soldiers, who react in the same terror Luigi did back in Mario Power Tennis. Like that game, his back is turned to us. I kinda like how we never see what's behind the mask. It helps to maintain that sense of mystery that's always been a huge part of the character.
11. Donkey Kong holding a shotgun
In Donkey Kong 64, one of the weapons DK can use is his Coconut Gun, which is made to look like some barrels slapped together. But during development, it originally looked like a realistic gun. Once Miyamoto saw it, he immediately drew up the design we know now.
Well, that's all I have time for today. It gets a whole lot darker from here. What does the top 10 have in store? Find out when I edit this page sometime tomorrow.

Super Mario Sunshine is absolutely terrible and by far the worst Mario game, even counting spinoffs. Fight me

Sorry, I'm calling CAP on number 2. The only Sonic games worth buying in the last decade was Frontiers & Mania.

OH FU-

I'M INNOCENT I SWEAR Also @lance4-_ i'm gonna kill you then revive you just to kill you again because you killed Lely

Have you even tried reading a Scottish accent? It is harder than it sounds and it doesn't even sound like a thing that would happen but I have experienced it.

any drinks?

exept idk how to use complete mode so RIP

@TheNudgyHampter @osc-omb @Fiery @xrunner48 @Dietsoda @Pixel @Princess_Tsurara (kinda) @ChocoM1lk