The 8 Saddest Video Game Boss Fights

Video games are uniquely positioned to pull at your heart strings. As a fully interactive experience, the right game will demand a more emotional response from the user than any other form of media thanks to the connections we make with a game’s characters, setting, history, and direct involvement in overcoming the challenges presented throughout the game.

In this blog post, Game Observer takes a look at 8 of the saddest boss fights in video game history. Be warned, there are spoilers ahead.

1. Glass Joe – Punch Out (NES)

Imagine being punched in the face by championship boxers for 40 years. This is the role that Glass Joe, sometimes called France’s Glass Jaw, plays in Nintendo’s long-running Punch Out! Series.

Glass Joe has featured as the tutorial enemy in every Punch Out! game released, and serves to ‘show you the ropes’, as it were, by taking punch after punch from the player character. Joe will very rarely attack the player, and almost never dodge an attack, meaning the glass jawed frenchman has probably taken about a million punches to the face since his debut fight in 1983 – poor guy.

According to the lore of Punch Out!, Joe has officially participated in 101 fights in his career, with a total of 100 losses to 1 win by KO; a feat which was achieved against the main antagonists of 1994’s Super Punch Out!, Nick Bruiser. In an issue of Nintendo Power Magazine, it was stated that Glass Joe beat Nick Bruiser in a freak accident, though details of this accident are scarce, and the win was never counted against Bruiser’s record of 42-0.

Glass Joe has provided a heroic service to fans of Punch Out! for as long as the series has existed, and should be honoured as a legend amongst gamers. After all, being the recipient of so many knuckle sandwiches for almost 50 years can’t have been fun for the frenchman. 

2. Giant Six – Little Nightmares II

Little Nightmares II is a truly unique gem. The series plays out more like a puzzle-platformer than anything else. Players are pitted against a new monster in each chapter of the series, and are tasked with escaping its terrifying clutches through a series of puzzles that usually include the added stress of grotesque and freakish creatures chasing the player whilst they search for solutions to the game’s challenges.

At the conclusion of Little Nightmares II we see Six, the protagonist of the first game, transformed into a terrifying gigantic version of herself. Our hero, Mono, must confront the transformed Six through a series of clever portal-like puzzles in order to save her from herself.

The fight itself is stressful, haunting, and challenging enough to keep players on their toes throughout. Seeing the once innocent Six scared and cowering in the corner of twisted rooms really pulls at the heartstrings after the 4-5 hours worth of bonding that has taken place between her and Mono leading up to this point, and using the ‘call’ mechanic; which is utilised throughout the game as a means of communication between the otherwise silent heroes, as a puzzle mechanic for the final confrontation is a beautiful callback to the earlier sections of the game.

The entire journey of Little Nightmares II is one of great sadness, and it is at the conclusion of this final battle that we see Six, now saved from her giant form, betray our paper bag-wearing hero at the last minute.

3. Sif, the Great Grey Wolf – Dark Souls (PC, PS3, Xbox 360)

The Dark Souls series has some of the saddest boss fights in video game history, whether by the content of the fight, or the mysterious lore surrounding the characters hiding behind the series’ iconic fog doors- but the Great Grey Wolf, Sif, is surely the most harrowing of all.

In the original release version of Dark Souls 1, players discovered a wealth of lore regarding one of the series best loved characters, Artorias, and his trusted wolf companion. In the game’s storied history, Artorias and Sif travelled to a land named Oolacile to save it from the corruption of the Abyss, but when pitted against the overwhelming force of darkness, Artorias realises his death is close at hand and decides to use the last of his strength to form a protective barrier around the young wolf.

Thousands of years later, the player pushes through the fog door of Darkroot Garden to be greeted by the protector of Artorias’ infamous grave: the Great Grey Wolf, Sif.

The fight itself provides a difficult challenge for first timers, utilising a unique moveset provided for Sif that sees the wolf gracefully dancing from one end of the map to the other, slashing, hacking, and slamming the player character with the use of a giant sword that the wolf holds in its mouth. Challenging as this fight be, it is nothing compared to the emotional drain presented to the player at the gruesome task at hand, one that sees them begrudgingly confront the loyal protector of Artorias’ grave to prevent the spread of the abyss once more.

Once the player has drained a large portion of Sif’s health bar, his animations change to show the poor wolf hobbling and limping around the stage, valiantly carrying on in the face of imminent death. If that wasn’t bad enough, the developers decided to add an additional level of sadness after players save the younger Sif in the Artorias of the Abyss DLC, introducing a new cutscene that shows Sif recognising the player character as his saviour from the past, and letting out a lamenting howl before he is forced to fight you again.

Oh Sif, we were not worthy of you.

4. Cutie the Elephant – It Takes Two (PS4, Xbox One, PC)

It Takes Two is one of the best co-op games released in the last decade. The story follows newly separated parents, Cody and May, on a fantastical journey as they work to rekindle their relationship through a series of challenges that perfectly reference famous game genres of the past. 

The opening hours are charming, fun, and brilliantly develop the relationship between the player characters through a mixture of co-operative missions and dialogue exposition. It comes as quite a shock then, when the game takes a decidedly dark turn after our heroes meet Cutie the Elephant, and are forced to murder the poor stuffed animal in order to gain the attention of their daughter, Rose, who they hope can free them from the their transformation into childrens toys.

The entire scene is genuinely harrowing, and seemingly comes out of nowhere. The introduction of Cutie as a character shows her to be innocent and friendly, but that doesn’t stop our ‘heroes’ from mercilessly chasing her down; forcing the player to drag the poor elephant across the map, tearing off various limbs from the stuffed animal, and throwing her to her untimely death. The way the entire scene plays out, and the button mashing mechanics implemented in order to drag the struggling character to her death, create a genuinely uncomfortable, and unforgettable moment, that is as shocking as it is horrific.

It would be easy to mistake this for a ‘kids game’ up until this pivotal moment in the story, but that assumption is extremely wrong.

R.I.P Cutie the Elephant. You didn’t deserve that.

5. The Boss – Metal Gear Solid 3 (PS2)

When MGS3 came out in 2004, we were blown away by the revolutionary new setting, survival mechanics, and graphical upgrade, but it was the story of this Soviet-era espionage epic that truly left its mark on video game history.

Metal Gear Solid 3 followed Naked Snake, the former antagonist of the original Metal Gear series, and father of Solid Snake, as he undertook a clandestine mission in the Russian woodlands to rescue former Soviet nuclear scientist, Sokolov. What follows is a truly unforgettable story of betrayal, redemption, and the horrors of nuclear warfare, as Naked Snake traverses the wilderness in search of ‘The Boss’, his former mentor and now a defector to the Soviet Union. The Boss’ betrayal may not have come as much of a shock at first, in what some people thought was a story beat that echoed tropes of the spy genre, but the eventual unravelling of her true intentions as a double-agent, whose focus was to thwart the efforts of a nuclear obsessed enemy in the height of the cold war, crescendoed into one of the finest redemption stories ever told.

By the time players reach the final act of the game, Snake is tasked with killing the Boss by his own hands. The fight takes place in one of the best endgame arenas ever made, one which has seen many callbacks in video games since, but the true beauty, and sadness, in this final battle comes from the Boss’ revelation that she was, in fact, never Snake’s enemy. It is after this that our hero comes to understand the Boss’ death is imperative so that she may be used as a scapegoat for earlier events in the game, and help America avoid an all-out war with Russia. What follows is a difficult emotional battle between two former lovers, where the player and the main character both understand that killing the Boss is morally reprehensible, but ultimately the only option if they wish to save the lives of millions from war.

Metal Gear Solid 3 is one of the finest games ever made, and the final act continues to be remembered throughout history as one of the greatest examples of how the characters in a video game can connect deeply with the players.

6. Astraea – Demon’s Souls (PS3)

The Maiden Astraea is the final boss of the most frustrating area in the original Demon’s Souls, the Valley of Defilement, which heavily features some of the most difficult platforming sections, enemy types, status inflictions, and red phantom invasions in the entire game.

At the end point of this area players are greeted by the Maiden Astraea and her protector, Garl Vinland. At which point players have the option of either fighting Garl directly, or traversing an alternative path to reach the maiden directly who, instead of fighting the player, laments to them at the nature of their task to gather the Demon’s Souls by mercilessly killing the innocent or downtrodden creatures of the world. If players choose not to attack the maiden, she will simply commit suicide after offering the player their ‘precious Demon’s Soul’, leaving the demoralised Garl Vinland to bow his head in shame.

7. The Last Guardian – Master of the Valley (PS4)

Fumito Ueda’s long awaited successor to Shadow of the Colossus captivated audiences when it was first announced, thanks to the charming dog-bird-cat creature, Trico, that stole the show at E3 2009. The game was originally announced for the PS3, but after a series of delays and almost a decade in development, Trico and the Boy (possibly a better title for the game), finally graced our screens on the PS4 in 2016.

Despite some awkward character controls and uncooperative AI for Trico, the Last Guardian was still an emotional and visually impressive experience that provided players with an enjoyable journey through a desolate ancient kingdom. The fighting mechanics were predominantly handled by issuing vocal commands to Trico, who would proceed to stomp, slam, and bite the enemies in its path.

At the final summit of their journey, the heroes find themselves set upon by a pack of evil Trico-like creatures, who attack both the boy and Trico in a desperate fight that sees our poor bird-dog companion savagely torn at by the enemy creatures – they even rip the poor fella’s tail off.

The final fight is emotional, and after the player figures out how to banish the evil creatures from the arena, we see Trico safely deliver the boy back to his village before flying off to the sunset. The ultimate fate of Trico is unknown, but his presumed sacrifice provides a satisfying but equally sad conclusion to the epic journey he and his small companion undertake throughout the game. The Last Guardian is a satisfying and concise journey, lasting around 12 hours, and one that is highly recommended for fans of Ueda’s previous work on Shadow of the Colossus and Ico.

8. Solid Snake vs Liquid Ocelot – Metal Gear Solid 4: Guns of the Patriots (PS3)

In the final act of the Metal Gear Solid series, Solid Snake finally confronts his long-time enemy, and his sort-of brother, in the form of Liquid Ocelot. Ocelot had been a recurring antagonist throughout the series, but it was in 2001’s Metal Gear Solid 2: Sons of Liberty, that Ocelot assimilated the arm of Liquid Snake, the antagonist of MGS1, and assumed his identity from there on.

MGS4 follows a truly desperate journey by Old Snake to finally stop Liquid Ocelot and the Patriots once and for all; both of whom were also at war with one another. Through a series of 6 story acts, players are met with betrayal, revelations on war and the true world order, and major character deaths in one of the best games ever made. Once Old Snake completes his final mission aboard the enemy vessel, Outer Haven, he is met by Ocelot to complete a final fight to the death between the 2 characters.

The fight itself is emotional, utilising 2D fighting mechanics for the first time in the series, but it is the subsequent story revelations that change player’s perspectives on the entire series that truly make this one of the greatest and saddest boss fights in video game history. The final fight in MGS4 is a masterclass in emotional direction and story development by one of the industry’s greats: Hideo Kojima, and is a fight that will stick with players for generations to come.

That concludes our list of the 8 Saddest Fights in Video Game History. Enjoyed this article? Why not read The Tragic History of Alpha Protocol.