Legend of Zelda: Encountering Wizzrobes

The original Legend of Zelda has some intense boss battles, but they aren’t always as annoying as other encounters. For example, fighting Wizzrobes can easily lead to you screaming at the TV.

These guys teleport around dungeons, fire long-range attacks, and always hunt in packs. And if you don’t have a Magic Shield to deflect their attacks, then you are likely to become a permanent resident of the dungeon floor.

Chrono Trigger: Golem Sisters Battle

With the right strategies, you can make the Golem Sisters fight in Chrono Trigger more bearable. On your first playthrough, though, this fight is downright rage-inducing!

The enemies can copy your abilities and throw your strong magic right back in your face. And if you don’t have some very specific gear, these twisted sisters will make short work of your entire party.

Ninja Gaiden: Bloody Malth Fight

If you make it as far as the Bloody Malth fight in Ninja Gaiden, you’re a damn good gamer. But this boss fight is one where you have to be lucky rather than simply good.

The boss channels lightning and shoots fireballs at you. The catch? The fireballs are almost impossible to dodge, and each hit takes three of your lifebars away!

Contra III: The Alien Wars: Fighting Big Fuzz

Contra III had plenty of memorable boss battles. But the fight against Big Fuzz is the first fight that seems downright unfair.

Despite the cutesy name, Big Fuzz is like what happens if a Terminator meets a Titan. First, you fight two smaller robots, which is an annoying battle unto itself. When the big robot appears, you need to dodge his fire breath while also dodging energy that follows you around. And just when you think you’re going to survive the fight, he starts throwing bombs that are almost impossible to dodge.

Castlevania: Fighting Death

The first Castlevania game is almost perfectly balanced. It is difficult without being an annoying grind, and the enemies get more complex as you learn more about how to play.

But the fight with Death is something else entirely. While the battle with Dracula is arguably harder, dodging death and his spinning scythes is enough to make anyone want to walk away from their NES.

The Lion King: Second Level

You might expect Disney games aimed at children to be a bit easier. But retro gamers know damn well that titles like Aladdin and The Lion King were among the most difficult titles Sega ever released.

In fact, the second level of the Lion King is a notorious platforming nightmare. It combines platforms, puzzles, and even an ostrich ride into one of the most difficult levels ever created.

Ghosts’n Goblins: Fighting Red Arremer

Ghosts’n Goblins has a reputation for being one of the hardest games ever made. And that makes it kind of hard to pick the most frustrating moment.

Looking back, the worst moment is your first fight with Red Arremer. He is fast, he flies, and he quickly reminds you how easy it is to die in a game where you can only take two hits.

Star Wars: The Empire Strikes Back: Probe Droid Fight

The Super Star Wars games on the SNES are legendary. But the Empire Strikes Back game quickly signifies it will be more difficult than its predecessor.

It all happens when you must fight a giant Probe Droid. You need to find angles to shoot it while avoiding fire, all while jumping on platforms that sink into the water. Land in the water and you’ll get electrified.

Basically, the game turns a droid that never did much in the movie into one of the hardest boss fights you will encounter.

Sonic the Hedgehog 2: Giant Robot Fight

The final battle in Sonic the Hedgehog 2 is very memorable. You are fighting Robotnik in a giant robot, and the fate of the entire world is at stake.

Just one problem: you must fight with no rings, meaning a single hit will kill you. And attacking the robot mostly means finding the exact moment where you can hit his belly and not his claws. After dying to this boss enough times, it’s tempting to give up and go play some Sonic Spinball instead!

Super Mario Bros. 2: The Lost Levels: Water Pit

Super Mario Bros. 2: The Lost Levels was the “true” sequel to the original game. But when Nintendo thought it was too hard for American gamers, we ended up getting a reskin of Doki Doki Panic instead.

You can play The Lost Levels now, and most of it is fun to play. But the first underground level has a section that looks like water where if you jump in, you fall to your death. It’s a petty and manipulative level design practically designed to make players walk away from the game.

Goldeneye 007: Fighting Jaws

Goldeneye 007 did many things right, including frustrating moments. That’s because developers put the most frustrating fight into an optional part of the game.

In the Aztec Control mission, Jaws functions as your “big bad.” And he takes a ton of damage before dying, meaning most players will die long before they put Jaws down.

How tough is he, though? We’ll put it this way: if you are using the Golden Gun which takes enemies out in a single shot, it actually takes multiple shots to kill Jaws!

Mega Man 2: Heat Man’s Platforms

Mega Man 2 was always my favorite game in the series. But it also contains some of the most frustrating franchise moments.

For my money, one of the worst parts was the disappearing and reappearing platforms on the Heat Man level. Eventually, you must travel over molten metal and bottomless pits, and unless you have help from Rush, you have to perfectly time each jump or you will fall to your death.

Teenage Mutant Ninja Turtles: Water Dam

The original Ninja Turtles game on NES is surprisingly complex and rewarding. Sadly, most players never got past the water dam.

The underwater controls are terrible and the map is unpredictable as you try to disarm some bombs. And even if you get good at understanding the controls and finding the bomb, electrified reefs can instantly kill you.

Forget the Technodrome. If Shredder had an underwater base, the turtles would all die on their first attempt to find it!

Mike Tyson’s Punchout: Mike Tyson Fight

There are plenty of hard moments in Mike Tyson’s Punchout, including run-ins with scary fighters like Bald Bull or Sandman. But nothing is as discouraging as the Tyson fight.

For the first 90 seconds, Tyson rains down blows that knock you out in one punch. And if you survive that, he throws in surprise punches to frustrate your attempts at finding a pattern. Players were far likelier to land a punch on their TV in rage than landing a punch on Mike.

Battletoads: Speeder Bikes

Battletoads is a great action platformer with some really exotic levels. Unfortunately, most players never made it very far at all!

That’s because of the damn speeder bike stage. This level is legendarily difficult, and even in an age of save states, it can be damn hard to make it through.