The hardest boss fights in video game history

By Jesse Lennox Published February 1, 2025

From the first console generation to the last, there have always been boss fights. These battles upped the difficulty to test players on all the skills they learned up until that point and push them even further beyond. Boss fights come in all shapes and sizes depending on the genre, such as shooters and fighting games, but they always stand as the game’s highest challenge. A perfectly tuned boss fight can be the highlight of a given game, but if it leans a bit too far one way or the other in terms of difficulty, it can fall flat. An easy boss fight is dull, but one that is way, way too hard can completely ruin a game. Thankfully, most games hide their intentionally punishing bosses as secret or optional challenges, but there are a few that have caused many players to give up before seeing the credits roll. We don’t know if any upcoming video games will feature bosses harder than these brutal battles from all of video game history.

One of the most unique aspects of Undertale is the fact that you don’t actually have to kill a single enemy. You can play the game as a complete pacifist and are rewarded for it. However, anyone who opts to go the opposite direction and aim for the genocide ending will be faced with the most difficult boss in the game: Sans. The normally cheerful and joking skeleton will show up as your final opponent to stop your rampage and will probably be successful. Each of his attacks, which play out in various iterations of bullet-hell-style dodging sequences, require near-perfect execution and memorization to avoid. Even though you will have a ton of HP at this point, even a single too early can ruin your run since his attacks will inflict poison and slowly dwindle your health away. Unlike most bosses, this one really makes you feel like you’re not supposed to win.

Boses in the NES era were notoriously difficult. Games were much shorter then, so they were extra difficult to make up for it. Mike Tyson’s Punch-Out!! is one of the first examples of a boss-rush game, where you go from one boss to the next in a gauntlet all the way to the end. There are tricks to each fight, Tyson included, but even if you know the tells it is still incredibly hard to execute. Tyson is fast, can knock you out in one or two shots, and only gives you a few frames to counter with that you need to hit perfectly. Dodge once in the wrong direction or jab one too many times and you will be down for the count. This isn’t so much a boss fight as it is a test to see if you’ve memorized Tyson’s moves and can perfectly execute the counters.

Fighting games are most fun playing against another player, which is what they were primarily designed for. There have always been arcade modes and other single-player offerings, but typically you had to grab a friend or head online to get a reach challenge. That isn’t true for Mortal Kombat 9’s version of Shao Kahn. The lord of Outworld does not fight fair. All of his attacks deal massive damage, he can juggle you off of almost any move, he has way more health than any other character, and can ignore hit-stun whenever he feels like it. Oh, and that’s not even mentioning how obvious it is that he reads your inputs to counter you. Even professional fighting game players struggle to beat this boss without resorting to cheesing him.

We were spoiled for choices when it came to FromSoftware bosses, but we challenged ourselves to pick only one. In the end, it came down to Isshin from Sekiro and Promised Consort Radahn from Elden Ring: Shadow of the Erdtree. In the end, we had to give it to the latter for pushing so many players to the limit. Even Miyazaki himself claimed that this boss was probably the most difficult boss they could make within the limitations of the game. Radahn is huge, fast, and seems to never let up on his attacks. And that’s just the first phase. If you somehow manage to find a way to get enough hits in without getting wiped, he gets an entirely new set of holy AoE attacks that make it nearly impossible to heal, dodge, attack, or even see what is going on.

Hollow Knight shares a lot of elements from the souls-like genre in addition to being a Metroidvania, but the bosses might just give FromSoftware a run for its money. Absolute Radiance is the final boss of the last DLC for the game that expects no less than perfection from the player. There’s only so much you can do to prepare in terms of equipping charms and upgrading your nail so it really does just come down to skill. Between their 6 phases, you will need to deal with rapid-fire beam attacks, summon swords, spikes coming out of the ground, and more. You only get a small window to get your attacks in so you can’t miss your shot or risk another onslaught of attacks. Even the most dedicated Hollow Knight fans have given up in the face of this challenge.

Nearly every Final Fantasy game hides away one or more super bosses that are meant to be end-game level challenges. In the original Final Fantasy 7, these were the various Weapons you could attempt on the final disc. Of all the Weapons, Emerald is typically considered the hardest. You need to head underwater to encounter this boss, which means you need to defeat it within a time limit. By default, this is 20 minutes but you can extend it to 30 if you’re willing to waste a Materia slot to equip the Underwater Materia. Odds are you won’t need to worry about that timer since it can deal over 50% of the entire party’s HP with a single attack, counters with a stomp that also hits the entire team, and also has a move that deals damage to everyone based on how much Materia you have equipped.

It is a little strange to call a song a boss, but there’s no other way to describe playing Through the Fire and the Flames on Guitar Hero 3. The difficulty of this song is based on the song, as every song is, but we almost think it would be easier to learn the song on a real guitar than keep up with the notes blazing down the track. Words can’t accurately describe how insane it is to watch this song be played by someone skilled enough to somehow keep up. The notes are so clustered to gether that it would be impressive if anyone could hit them all at half the speed the game asks.

We’re giving one honorable mention to the Absolute Virtue boss from Final Fantasy 11. We didn’t want to include bosses from live-service or MMOs on this list, but we had to highlight just how insane this boss is. Initially, FF11 players thought this boss was actually unbeatable after spending literal hours fighting it with no progress (excluding illegitimate methods). Some teams had gone upwards of 30 hours fighting it but couldn’t take it down. It was so extreme that it remained undefeated for years until Square Enix released a patch that cut its HP almost in half and nerfed many of its stats. To compensate, a 2-hour time limit was also put on the boss. Only with all of that, plus the level cap being raised from 75 to 99, did players finally manage to overcome this legendary boss battle.