When it comes to high-pressure adrenaline-loaded action in gaming, there’s really nothing quite like a serious boss fight. Coming face to face with the big bad waiting at the end of the level can induce some sweaty palms, clumsy fingers, and disorganized thinking in a hurry. And when that boss is unusually difficult to down, it can also inspire some serious frustration.

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There are many notable boss battles in the Nintendo 64 canon and the toughest of the tough rank up there with the most excruciating of all time. These bosses were enough trouble back in the day to make a player lose all hope, yank the cartridge out with the system on, and possibly even return it to the Toys R Us it came from.

8 Wizpig – Diddy Kong Racing

Perhaps the most notoriously excruciating N64 boss fight of them all is Diddy Kong Racing’s big bad, Wizpig. The initial race against him is done in a kart, with trees falling all around the track and the unscrupulous pig wizard even cheating for a head start. The second race is in the tricky-to-control plane, and it’s harder in every single way.

Without knowing that they can let go of the A button when hitting a boost pad to get an extra blast of speed, it may not even be possible for players to beat this boss. And even knowing this little secret is only enough to down him if they execute a just about 100% flawless run. This game is becoming a more forgotten gem as years go by, but anyone who played it long enough to reach this nightmare most definitely hasn't forgotten.

7 Boba Fett – Star Wars: Shadows Of The Empire

Boba Fett Standing Shadows of the Empire

Shadows of the Empire is a notoriously difficult game altogether, which has been an area of criticism for an otherwise highly appreciated Star Wars entry. The difficulty is a selling point for some, but even the most masochistic fan should be able to admit that the Boba Fett fight is just plain unfair.

Learning how to locate the bounty hunter and avoid his attacks while landing some on him is exceedingly difficult in and of itself, but even after defeating him he pulls one of the dirtiest tricks in the boss battle playbook and hops in Slave 1 for another round of painstaking combat.

6 Ganon – The Legend Of Zelda: Ocarina Of Time

Adult Link facing Demon King Ganon at the end of Ocarina of Time

It’s incredibly important for any great and challenging game not to leave players feeling a sense of anticlimax with their final boss battle. Considering the fact that Ocarina of Time is a legendarily great and challenging game, it sort of goes without saying that its final boss is far from anticlimactic.

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Ganon always proves to be an epic foe, and in this case, he’s also an irritating one. His first form isn’t all that fearsome, but once that Master Sword is knocked away and the Demon King is approaching, things can get pretty dicey.

5 Hard Mode Andross – Star Fox 64

Andross' head in space in promo art for Star Fox 64

While in most instances the journey to a boss fight probably shouldn’t be considered an aspect of the fight itself, Star Fox 64 is a unique case in which that’s just the undeniable truth. Rather than swapping through difficulty settings to achieve a greater challenge, players in this game must meet certain goals to control their trajectory through the game map in order to experience its hardest difficulty. One wrong move and the path is changed, meaning no Hard Mode Andross.

Difficult path aside, Andross himself is still plenty difficult to defeat once he’s reached. The battle begins on a treacherous course through a temple that’s liable to steal the player’s precious upgrades in the blink of an eye. Then, once the giant-faced creep is reached, things don’t get much easier. Coming out victorious on this one is almost more relieving than exciting.

4 The Beastector – Mischief Makers

Bestector Mischief Makers

Mischief Makers is a seriously underrated but also seriously challenging game. There are several bosses throughout this title that can push a player to the edge of their own sanity, but the final battle involves just about all of them, so it’s fairly easy to call it the toughest.

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The Beastector is a super cool Megazord-looking robot, only this one doesn’t fight evil, it just is evil. Avoiding damage can feel impossible at first, and that’s because it almost is, but with enough perseverance players will ultimately find themselves grabbing him by the foot and shake-shaking him into oblivion.

3 King Krusha K. Rool – Donkey Kong 64

Donkey Kong 64 boss looking through barrel at boxing K Rool

Some bosses provide their challenge by throwing an obscene number of attacks at the player, some do it by making an inscrutable puzzle out of figuring out how to hit them, and some, like King Krusha K. Rool of Donkey Kong 64, does it by taking absolutely forever to take down and being timed.

This is a wildly long boss fight, and to add to the frustration if the player happens to lose at all they have to start from the very beginning. This irritating little wrinkle is fitting, actually, because although this Expansion Pak-packing title is beloved among N64 fans. It’s also notorious for its painful amount of backtracking.

2 Bowser – Super Mario 64

bowser mario 64

Spectacular hand-eye coordination can serve any gamer well in a plethora of situations, but it’s rarely more important than it is in the final battle against Bowser in Super Mario 64. The fight is fairly straightforward, as it’s almost identical to the other times players must battle him throughout the game, only this time things are made far more tricky when the stage breaks down into the shape of a Power Star, which makes tossing King Koopa into the conveniently placed spiky mines something of a nightmare.

Those with incredible aim and an uncanny grasp of the awkward camera angles this game provides may find this battle fairly simple, but for everyone else, it can be treacherous. It makes for one of the most classic Mario fights ever.

1 Mizar – Jet Force Gemini

Mizar Jet Force Gemini

This boss battle could have been a recreation of Bowser in the first world of Super Mario Bros. for the NES and Jet Force Gemini would still be considered among the hardest Nintendo 64 games ever made. That’s not the case, though, because it is really tough.

Mizar employs the classic boss tactics of blasting a seemingly unavoidable barrage of attacks that drain an obscene amount of damage with a single hit and combines it with the added nightmare of offering players no opportunity to acquire more health or ammo. Any player to have cleared this demon deserves some sort of collectible Nintendo ribbon.

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