I have been playing through Cyber Shadow and as I was doing so I couldn’t help but contemplate how well designed the bosses in that game are. I began to think back to some of my favorite bosses and realized that there were some great standout encounters in the past decade, many of them most memorable and challenging bosses in gaming history. Whether these villainous encounters were memorable for their narrative impact, zany encounter, or the difficulty they posed for the player, the bosses on this list all come from different types of gameplay. All the games included in this list are from 2010-2019 and there can only be one boss per series.
Also, you may recognize there are a couple notable exceptions in the list and that is because I have missed the entire PS4 generation. I do recognize that God of War and Bloodborne are two examples of potentially great boss encounters but instead they are on my list to play! I will get to them I promise. With that, let’s dive into my most memorable bosses fights of the past decade.
Sunset Overdrive- Fizzie
Sunset Overdrive is one of the most underappreciated games of the last generation. From the wacky weapons to the partially dated pop culture references, the game is fun for just being one of the most like, well, a game. Sunset Overdrive is about having fun and not getting too bogged down in the details. Jump, grind, and dash across a post-apocalyptic city brought to ruin by the latest energy drink craze while the true enemy is capitalism!
There are hints that the company behind the zombie genesis might have known more than the public was led to believe and this is only confirmed when you come face to face with the mascot of the company, Fizzie. Fizzie starts out as a giant balloon with laser eyes and a serious potty mouth. You are tasked with playing gymnastics on the top of a skyscraper while avoiding all of Fizzie’s attacks until you can get shots off at him. It’s a fun and strange encounter that helps to cements Sunset Overdrive as a classic in my book.
Minecraft – Ender Dragon
The only real challenge that Mojang ever put in the game; the Ender Dragon is the culmination of most player’s long hours in the game. It is a challenge in and of itself to even get to the battle which means heavily exploring the Nether and Minecraft main world for various items and the End portal. Once a player gets access to the End, they still have the Ender Dragon to contend with and will need to come prepared for the battle especially if they are running the battle solo.
The Ender Dragon is tough so enchanted weapons and armor are highly recommended to stand a chance against this sweeping threat. The final challenge of minecraft may not be the most exciting fight but it makes the player pull out all the stops in their playstyle to slay it. Or you could just use some beds but that’s a different conversation.
Bioshock Infinite – Zachary Hale Comstock
There are so few storylines that have stuck with me in gaming like Bioshock Infinite’s and part of that is because of the reveal of the true villain of Columbia, you. Or I should say Zachary Hale Comstock, the version of you that tried to repent for his sins during the war but got carried away with his own beliefs.
The gameplay leading up to this realization is nothing different from the rest of the game unfortunately which is what prevents it from being higher on the list. It does have some of the best use of the skyline and sky hook mechanics but that says more about Infinite’s inability to capitalize on its biggest gameplay hook rather than the effectiveness of the final battle. However, the ending of Infinite is such a great conclusion to a story of personal tragedy, addiction, compassion and guilt. The Bioshock series always gave you these gut punches that stayed with you long after you turned off the game. I just wish 2K would punch us in the gut one more time in the Bioshock universe.
Portal 2 – Wheatly
I almost forgot that Portal 2 came out in 2011 because the game just feels like such foundational part of the videogame landscape at this point. Portal 2’s finale stars the bumbling core Wheatley trying his best to stop Chell from reinstalling GlaDOS into Aperture’s main computer. To do this, Chell must work with GlaDOS and install corrupted cores into Wheatley while suffering poorly constructed insults from incompetent core.
The gameplay requires the player to do more of what they have done the entire game while meeting some of the most outlandish core personalities in the series. After Wheatley is successfully sucked out into space with his new best friend Space Core, the player is rewarded with one of the most memorable final scenes in any game as GlaDOS apologizes (sort of?) for the events of the past two games and sets the player free with a song and a long lost companion.
Borderlands 2 – The Warrior
The Borderlands series is known for two things: its seemingly infinite supply of weapon variety and the enemies you kill with said weapons. Borderlands would not be the same if there were not some memorable and hard hitting boss fights to go along with that formula and though there are harder bosses, the Warrior fight I believe is the most balanced and fun. The Warrior is Handsome’ Jacks final surprise for the Vault Hunters, as he unleashes this beast.
The Warrior fight itself involves rising and falling lava levels, giant stomps, and fire breath. All the while, other enemies are popping up from the ground and Handsome Jack taunts you from the sidelines until you are able to hit the final shot in the Warrior and send an explosion of loot into the sky, which is the universal signal of a job well done. The fight is a satisfying conclusion to Borderlands’ second trek around Pandora and now, I guess, all there is to do is to go and try to kill Terramorphous the Invincible.
The Legend of Zelda: Breath of the Wild – Calamity Ganon
The Breath of the Wild is a modern classic and there is little debate about that but there is quite a bit of controversy when discussing some of the classic Zelda tropes within the game. Whether people have issue with the lack of themed dungeons, weapon degradation, or obscene amount of collectibles, people have some criticisms but the most egregious criticism is the final boss of the game with Calamity Ganon. The boss had been hyped up from the moment the player walked barefoot into the Hyrulian sun so hype for the fight was high for many players but I believe it takes the best parts of combat and story progression to create a fight that is narratively appropriate yet offers some challenge for players.
The fight can be activated at any time during the game, since the player can go right up to the castle. The fight is as tough as you make it out to be but if you do everything in the game, Ganon will start with half health and Link will have additional abilities to crush Ganon down even further from the start. After the abilities have been exhausted, it is on the player to remember their dodging , parrying, and strategies to whittle Ganon down the rest of the way. The only reason this fight is not higher is because the final form (if it counts as one?) overshadows some of the satisfaction of defeating the harder phases of this fight.
Arkham City – Mr. Freeze
Batman usually makes unreliable alliances with the villains in his universe and Mr. Freeze in Arkham City is no different, as Mr. Freeze promises to help Batman create an antidote after he was exposed to Joker’s poisoned blood. Mr. Freeze changes the terms of the agreement though and Batman doesn’t have time for Mr. Freeze’s proposition so the two fight over the rights to the antidote.
The Mr. Freeze encounter is excellent for forcing the player to think outside their normal playstyle with Batman. Unlike most of the other bosses in the Batman Arkham franchise, Mr. Freeze learns as Batman scores hits on him which means Batman needs to use all his fighting skills and every tool in his utility belt to pull a victory out in this fight. The only bad thing about this fight is that it points to many of the glaring issues with many of the other Batman Arkham boss fights since none of them adapt to your techniques and can be defeated with the same repetitive techniques.
Cuphead – Grim Matchstick
Of course Cuphead made the list but I had a little bit of trouble choosing just one of these spectacular boss fights. Cuphead’s main schtick is being a bullet-hell gauntlet of boss fights and each boss has its own unique personality and fight patterns. Each fight is challenging in its own right but I believe the boss that perfectly takes all the elements of Cuphead and makes the player really use what they have learned the most is Grim Matchstick. A mighty dragon defending his castle, Grim Matchstick is often a wall for many new Cuphead players. Grim Matchstick is split into 3 phases and each phase is harder than the last.
The entire level requires that the player hop from cloud platform to cloud platform so as to not get hit or lose their footing while the big burly dragon works through his powerful phases. The first phase is easy and is just getting the player used to the platforming as Grim Matchstick shoots fireballs and eye beams to dodge, while the second phase brings on an army of fire demons who throw themselves at the player with increasing persistence. After the player is able to beat up Grim Matchstick enough, he transforms into his final and toughest form, which makes him the Cerberus of the skies with his three fire breathing heads. Grim Matchstick can be one of the toughest fights in the game while also serving as a final training ground for the player to succeed in the rest of the game. The platforming is tough and the dragon is heated but success is only a matter of practice.
Dark Souls – Asylum Demon
The Demon Souls series is known for its boss fights and this entire list could be made exclusively of the various challenges that Dark Souls poses for players, however the original Dark Souls’ Asylum Demon takes this spot for being the thesis for the entire series. For the vast majority of players, this boss will serve as a lesson in running to fight another day but for others it can serve as a test of will and persistence. The boss is completely beatable, though very slowly, when you first meet his bloated body in the ruins of the asylum but running will reward the player with a high ground advantage.
Players can learn that jumping from high up can hurt enemies more, that enemies are not necessarily meant to be beaten as you meet them, and that exploring the world of Dark Souls is likely to give you useful benefits that you can exploit later. The fight will stick with player’s through the entire game (and for some the entire series) as they continue to build upon the skills and knowledge they learn during encounter. The entire point of a boss fight is to act as a final test of the lessons that player’s need to succeed after all.
Hollow Knight – Nightmare Troupe Master Grimm
A short lived ally, Troupe Master Grimm is the most memorable and arguably the toughest boss by itself and that is before we consider his Nightmare version. The change in aesthetic that Grimm brings to the game is also a welcome change of pace with the blood red ascents of Grimm’s tent, clothing, and lights being especially alluring and mysterious as the troupe leader talks about his rituals. When the player has everything in place for the ritual, it is revealed that Grimm was only using the Knight to collect the flames of the kingdom. The proceeding fight is fast and ruthless where there is no room for error.
The first battle is tough but Nightmare Grimm is on a completely different level as Nightmare Troupe Master Grimm has no mercy for the spry little knight as he sends energy balls, demon shades, and sharp tentacles to take you out. The player can’t relax for a moment as each attack happens in succession and only gets faster as the show wears on while the cultish audience cheers on your demise. Troupe Master Grimm is the best looking and the most fast paced fight in the game and I really hope that the Troupe makes an appearance in Silksong but maybe I am hoping for too much.
The Game Campaign 
My lord, the entirety of Cuphead was pretty darn challenging. At least it was fun and kept me interested. Thanks for sharing!
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I was worried I’d never beat it! Hopefully the DLC is just as fun as the original game
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