Top 10 Funniest Video Game Boss Fights

Top 10 Funniest Boss Fights in Video Games

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Welcome to WatchMojo, and today we’re counting down our picks for the Top 10 Funniest Boss Fights in Video Games For this list, we’ll be looking at some of the most hilarious big bads we’ve encountered over the years. Some of them will be end-bosses, so be warned that there are some spoilers. Did a different bad guy have you cracking up? Let us know in the comments!

“Super Paper Mario” (2007)

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Francis isn’t like the hulking monsters and sinister maniacs who make up most of the videogame world’s rogues gallery. A geeky chameleon who spends most of his time on his laptop, he’s perhaps one of the least intimidating bosses you’re ever likely to encounter. The closer our heroes get to him, the more pathetic he becomes - describing his kidnap victim as his “only offline friend” and setting his fort security so that only “Francis or hot babes” can enter. When this leads to him coming face to face with Princess Peach, he immediately becomes tongue-tied. After losing that fight, he actually pops up again later on but doesn’t fare much better. He’s the kind of villain that’s hard not to laugh at.

“Metal Gear Solid 3: Snake Eater” (2004)

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Like cardboard boxes and elaborate geopolitical conspiracies, wacky boss fights are a trademark of the Metal Gear Solid franchise, and the third game brought us the world’s oldest sniper, The End. While the player can engage him in an epic, nail-biting sniper battle, they can also just set the internal clock on their console forward a little and watch him die of old age. It’s the same sort of meta-gag which made Psycho Mantis such an iconic boss in the 1998 game. A psychic who would taunt the player about the contents of their memory card, Psycho mantis could only be defeated by switching controller ports.

When your hero is a space-traveling worm, it’s always going to be a challenge to provide them with an antagonist who’s even sillier than they are. Enter Bob the Goldfish. Confined to his glass bowl, Bob is jealous of Jim’s suit and plots to steal it for himself. Naturally, Bob can’t put up much of a fight and relies upon his feline bodyguards to battle Jim on his behalf. Once his goons have been dispatched, the actual showdown with Bob tends to be a bit of a comic anticlimax - never more so than when Jim simply grabs Bob out of his bowl and swallows him whole.

“Borderlands 2” (2012)

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Stop us if you’ve heard this one before: a crooked one-time casino owner becomes President, boasting of his own importance and denigrating everyone else around him. We are, of course, talking about Handsome Jack! He’s a monster of a man who gleefully threatens people’s lives for not bringing him pretzels quickly enough. Quick with a clever line and dementedly committed to his own vision of personal greatness, Jack sure is evil, but he’s also very entertaining. Like a true villain, he remains monologuing right up to the moment the player puts a bullet in his brain. By that point, you may have grown so fond of his egotistic ramblings that you almost don’t want to pull the trigger. Almost.

“Ghost of Tsushima” (2020)

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With its painterly visual style and sombre echoes of Akira Kurosawa films, “funny” isn’t really the first thing that comes to mind when you think of this samurai epic. Ghost of Tsushima, however, still knows how to pull off a great gag once in a while. When Jinroku challenges you to a duel, the scene is perfectly set for a classic sword fight. The two fighters stare each other down under the moonlight on a quiet hillside, slowly unsheathing their blades. The tension builds steadily up to breaking point and then...Jinroku throws down his sword and begs for his life. It’s a perfectly executed bit of Indiana Jones-ish misdirection.

“The Secret of Monkey Island” (1990)

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LeChuck is an undead pirate captain with a devilish mind, a horde of ghostly crewmates at his command and a few nasty voodoo tricks up his sleeve. All things considered, he should make for a formidable foe. Having gone through the classic video game bad guy playbook of capturing the hero’s girl, LeChuck makes it all the way to the altar with his kidnapped bride-to-be. When our hero, Guybrush, crashes the party however, he discovers that Elaine (E-Lane) has already rescued herself. Rather than an epic battle, the player then gets drawn into a verbose insult match. Thankfully, this is a talent that Guybrush has been honing with his Insult Sword Fighting Lessons earlier in the game.

“Fallout 3” (2008)

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You’ve trudged across Fallout’s irradiated wasteland and survived countless deadly encounters— making all kinds of grisly moral compromises in the process. Finally, you’re standing face to face with the man responsible for starting the whole thing— Colonel Autumn! While gamers might have expected some sort of epic showdown with the game’s big bad, Fallout 3 chooses to play it as a dark joke—allowing the player to use the V.A.T (word not acronym - rhymes with “rat”) mechanic, take aim at Colonel Autumn’s head and blow him away like they would any other enemy. Ultimately, Autumn is just another human being, not a supervillain or monster. This makes for grimly funny anticlimax. If that’s not really your style of comedy, you do get the chance to insult him for a bit first.

“Mario + Rabbids Kingdom Battle” (2017)

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Combining the odd world of Super Mario and those raving Rabbids was always going to lead to a lot of bizarre sights. The game’s subversive sense of humor, however, is all part of its overall wacky charm, and nowhere is that more perfectly encapsulated than in the boss battle against the hulking Rabbid Kong. After scaling a giant tower in preparation for his last stand, Rabbid Kong is unceremoniously toppled by a chaos-hungry Rabbid Peach. He still manages to pose for a selfie on the way down, though!

“Conker’s Bad Fur Day” (2001)

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There are few games in existence as infamous as Conker’s Bad Fur Day. The game’s plot sees Conker trying to make it home to his girlfriend after a night of heavy drinking only to find himself pursued by the Panther King. As he gets increasingly side-tracked from his main mission, Conker faces off against all kinds of bizarre bad guys, but nowhere is the game’s childish, weird-out sense of humour more overt, however, than the battle with the Great Mighty Poo. It’s not a nickname! He’s a literal pile of opera-singing excrement who must be defeated using toilet paper and a great mighty flush. Gross.

“South Park: The Fractured but Whole” (2017)

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In true South Park style, the hardest boss fight in the whole game comes courtesy of someone no right-minded human being would ever dream of tussling with. That’s right, we’re talking about the man who convincingly voiced God himself, Morgan Freeman. It’s an optional boss fight, but the player best be ready should they choose to take on the beloved actor. If signature moves like Glistening Freckles don’t get you, the Million Dollar Bitchslap just might. The game has lots of hilarious showdowns but this one most effectively captures the “what the heck am I watching” feeling of all the show. It also makes for one of the most unforgettable boss fights in recent memory.