For a lot of gamers who came up during the heyday of the NES, most modern boss battles are a breeze. Back in the day, you might have a couple of extra lives, but saving and restarting wasn’t a thing in a lot of games. Eventually, players would reach a point that would grind their game progress to a halt if they couldn’t figure out a way past in a few tries. That usually ended up being a boss battle.

In the litany of thumb-destroying boss battles that occur in numerous NES games, there are still a few that standout as the toughest of the tough. They also still probably cause players to toss and turn at night all these years later.

10 Bowser: Super Mario Bros.

The most iconic franchise in Nintendo’s history involves a certain Italian plumber named Mario. Over the course of the last few decades, Mario has appeared in dozens of video games in different styles, and Bowser has been his most consistent enemy.

While it seems absurd to say this now, beating Bowser was a huge deal when Super Mario Bros. came out in 1985. It took a lot of practice and finesse to stop him, but, once players had the rythem down, it wasn’t all that difficult. After all, this fight usually lasts all of two or three seconds.

9 Wood Man: Mega Man 2

The Mega Man series has proven to be one of the most popular video game franchises in history. That’s due in no small part to the fact that Mega Man is a character who is almost as iconic as Mario. But, those games have often been as difficult as they are popular.

Mega Man 2 continued Mega Man’s battle with Dr. Wily and his super nasty robots. While each one of the boss fights was difficult in its own way, the battle against Wood Man stood out as one of the toughest boss battles of all time.

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8 The Jaquio: Ninja Gaiden

The first game in the Ninja Gaiden series launched in 1988 and followed the exploits of Ryu Hayabusa. He travelled to America to avenge the murder of his father, which he discovered was committed by the Jaquio.

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The Jaquio’s plan was to release demons on Earth that he would control. Naturally, Ryu ended up fighting the Jaquio and ultimately defeating him, but the battle is is incredibly difficult, and the level of difficulty keeps getting upped throughout the fight.

7 Yellow Devil: Mega Man 3

When Mega Man 3 released, fans were looking forward to another great entry in the series. They thought that the boss fights couldn’t get more difficult than Mega Man 2. Then, they met the Yellow Devil.

At this point, the Yellow Devil is one of the most infamously difficult boss fights in the history of video gaming. It’s not impossible to beat the rogue robot, but that doesn’t mean anyone playing the game is going to do it on the first, or even 50th, try. There is however, a pretty easy way to cheese the figght by pausing and unpausing at the right moment—in the original NES release, at least.

6 The Technodrome: Teenage Mutant Ninja Turtles

The first Teenage Mutant Ninja Turtles game for the NES is one of the most notorious games of all time for the system. It was overrun with badly designed levels and borderline game breaking glitches. Yet, it somehow managed to still be a fun, engaging game.

While there were numerous levels in the game that were so frustrating that the player just wanted to give up, fighting the Technodrome was easily the most difficult boss fight in the game. That’s saying a lot.

5 Jaws: Jaws

One of the most iconic movies ever made is Jaws. The tale of a massive, man eating shark tormenting a seaside town remains as incredible today as it was when it first came out. A video game tie in was released on the NES in 1987, though it was based on the overall film franchise.

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The game saw the player controlling a boat, then fighting off various sea creatures with a diver. As one would expect, you have to beat Jaws to win the game, but doing so requires absolutely perfect timing that can seem almost impossible. That’s because it is almost impossible.

4 Dark Link — Zelda II: The Adventure Of Link

Much like the multitude of games featuring Mario, the adventures of Link have become synonymous with Nintendo. Games with the character have appeared on virtually every Nintendo console and handheld devices.

The second installment in the franchise is generally considered to be one of the best Nintendo games ever made. Fighting Link’s evil doppelganger is an incredibly tough encounter, even for masters of the game, and takes a lot of preparation to be ready for. That said, much like Mega Man‘s Yellow Devil, there is a pretty easy way to overcome the faceless foe.

3 Stage 7: Contra

When people talk about the hardest games of all time, Contra had better be part of the conversation. The game is brutally difficult, and it absolutely punishes anyone who choses to play it. Of course, as every NES aficianado knows, that makes the eventual victory all the sweeter.

The level design was quite complex and featured a variety of perspectives. Busting through the gates at the end of each level is always difficult, though the Stage 7 boss is particularly hard. That being said, none of them are easy.

2 Dracula: Castlevania

An enduring multimedia franchise, Castlevania got its start on the NES in 1986. The main character is Simon Belmont, a vampire hunter looking to destroy Dracula. It was easy to guess where this game was taking the player.

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Fighting Dracula was inevitable conclusion of the game, and it was a hell of a fight. Few gamers these days can claim to have beaten this one without the use of savestates, and braving this adventure on the origianl NES is worth some serious bragging rights!

1 Mike Tyson: Mike Tyson’s Punch-Out!!

When Punch-Out!! originally came out in arcades, Mike Tyson wasn’t actually in the game. Then, it was ported to the NES, and the game became Mike Tyson’s Punch-Out!! That’s when things got really tough.

As if the game wasn’t already hard enough, Mike Tyson’s appearance as the final boss made it borderline impossible. Beating him is a matter of patience and perfect timing. Even then, players still need a lot of luck on their side.

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