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5 Unsettling Boss Fights in Retro Games (That Made Me Question My Gaming Decisions)

As kids, we were ill-equipped to deal with some of the more unsettling boss fights.

Boss fights in retro video games kept the player guessing. You might find yourself fighting a giant baby like in Zombies Ate My Neighbors or a giant robot version of a narcissistic character like Dr. Robotnik’s Giant Mech Suit in Sonic 2. Some of them were really awesome, but every once in a while the boss fights were a little too freaky for their own good. Here are five unsettling boss fights from retro games that made me sit back and really think about what I was witnessing.

5. Mike Tyson in Mike Tyson’s Punch-Out!!

The monster himself.

 “My style is impetuous, my defense is impregnable. I’m ferocious. I want your heart”

Mike Tyson

This one isn’t unsettling because of the boss himself. He’s scary because he’s a tame version of the real thing. The reason I have to start this list with Mike Tyson is that he is a real-life, human boss fight. If you aren’t familiar with Iron Mike, take a few minutes to go watch some of his fights. 

…I’ll wait.

Did you see that? The guy was scary in the ring and out of it, and I grew up watching his fights.

Mike Tyson was simultaneously the most entertaining and horrifying individual in boxing when I was young. He would weave around his opponents’ punches, unleash a flurry of devastating blows and look like he enjoyed every minute of it. 

So, when the opportunity came to play Mike Tyson’s Punch-Out!!, I was thrilled to fight the champ. Naturally, as a little kid, I was too busy getting beat by King Hippo to try him, but my older brothers did get to him and got mopped more than once. 

Now, the unsettling part about this boss fight was that I started playing this game right around the time Mike was starting to go off the deep end. Here I am watching the news about him getting sentenced to jail for some terrible crimes, and he’s in my video game. Not only did that make him a little more intimidating, but I also had to sit back and think about which was scarier- the video game or the man himself.

Another thing to consider was that the real Mike Tyson sounds like a video game boss when he speaks. Some Mike Tyson quotes include:

“I just have this thing inside me that wants to eat and conquer. Maybe it’s egotistical, but I have it in me. I don’t want to be a tycoon. I just want to conquer people and their souls.”

“How dare they challenge me with their primitive boxing skills?”

In the game, when you finally beat him, he gives you some words of encouragement. But look at this face. Those are not the eyes of a happy person. They’re the eyes you’d see in a shark.

“I’ll be seeing you again real soon.”

I don’t think we beat him. I think we just made him angry.

4. Creator in The Final Fantasy Legend (SaGa in Japan)

Have you ever wanted to punch a deity in the face?

Well, before the days of God of War, we had The Final Fantasy Legend, a Gameboy RPG that was actually pretty good in most respects. 

Anyway, you battle through different worlds as you climb a tower that is supposed to lead to paradise. Pretty basic stuff, right? Well, it turns out that the whole thing was set up by the Creator. 

That’s right. All the suffering your characters lived through and the trials faced by the people trying to reach paradise in the past were just players in a complex game. Apparently, the Creator wanted to see if heroes could defeat the evil in the tower. The Creator made everything happen for his entertainment.

So, there you are standing before a deity that nonchalantly tells you that you did all that for basically no reason, and he offers you a wish as compensation. Not one for every party member. Just one. Next thing you know, you’re fighting the creator of your world. Eventually, you win and go back home without a wish because I guess the game ran out of space to give you a happy ending. 

To recap the situation: you beat up a god, maybe THE god, after learning that you were just pawns for his amusement. He was perfectly fine with killing you and a bunch of others along the way. That was pretty unsettling to say the least.

The implications in the game world are terrible because your characters apparently pack up and go home, knowing that they are ants and that other cosmic forces have the magnifying glass.

As far as the real-world implications, that’s some heavy stuff to drop on someone in the last 15 minutes of the game.

3. Belcha: Donkey Kong Country 3: Dixie’s Double Trouble

“Hey, remember when you didn’t have nightmares? That’s done now.”

What has Donkey Kong been doing since he first appeared in game-form in 1981? He’s been yeeting throwing barrels at people and breaking them open. What’s the worst thing that you could find out about those barrels? That they could be alive and sentient

Well, Belcha, a giant pissed-off barrel, seems kinda upset about the whole situation and tries to kill you. I’m not trying to read too much into this boss fight since Donkey Kong games are just silly fun. 

However, is it just maybe possible that we killed one of the other sentient barrels at some point during our zany adventures? Perhaps one related to Belcha? Is this our comeuppance for the misdeeds? Even worse, since we steamroll past this early boss, are the rest of the weaker barrels condemned to die knowing that their strongest fighter wasn’t enough? Perhaps that Creator fight did more to me than I thought. 

2. Mecha Hitler from Wolfenstein 3D

Questionable historical accuracy

So, you spend Wolfenstein 3D shooting your way through the hordes of enemy soldiers and bosses in different “episodes” of the story. Well, in the last part of one of these episodes, you get a fight with Mecha-Hitler

On one hand, who else would you have as a boss in a game about Nazis? On the other hand, it’s Hitler in a mech suit with four chain guns.

This fight, which I only took part in recently, made me stop and stare at the screen for a minute. After I had turned Hitler into a pile of goo, of course. I don’t think it was irreverence, either. Sometimes it feels better to go with a monster that nobody expects instead of the real thing.

1. Vortex Queen from Ecco the Dolphin

The first time I played Ecco the Dolphin, I was about four years old. So, I didn’t get into the game very much. I swam around, bumped my head, and never really advanced too far. It’s a very relaxing game, though. 

I picked up the game again a couple of decades later and it blew my mind.

You start out swimming in the ocean and communicating with other members of your pod. From there, you open new areas and watch as the game slowly loses its mind.

I’m talking about taking trips to Atlantis, some time travel, and going into space for a showdown with the big bad. It sounds ridiculous just writing about it, but that’s what happens. 

“What did I just get myself into?”

While in space, you encounter the Vortex Queen, a massive alien being that had eaten the members of your pod earlier in the game.

Just to recap: we went from swimming in the pristine ocean to fighting this Alien-inspired horror in outer space. Not only is that one frightening monster, but you’re totally unprepared for that thing to appear on your screen. You’re exploring the level, and then suddenly she is there in all her terrifying glory.

Naturally, you fight her and get your friends and family back to you. Then you go back to living in your nice ocean waters wondering what the hell you just saw. The ending gives you some vague closure, but seriously – what just happened?

Retro video games are special for a lot of reasons, but one of them is that they got away with some pretty unusual characters.

Whether you have real Mike Tyson and pixelated Mike Tyson fighting for the title of “scariest human being” or you’re questioning reality thanks to a malevolent Creator, it’s safe to say that some retro bosses were just plain unsettling. 

(Into retro games, huh? Check out The Ghetto Gamer’s Guide to Collecting Retro Games.)

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