10 bosses we still feel guilty about killing

James is a freelance journalist who has written for the likes of PC Gamer, Games Radar, Kotaku, LoL Esports, and many more. When he’s not writing about games, he’s usually playing them.

You had to beat them, you had no choice, it's not your fault. You monster.

We don’t usually feel bad for beating and overcoming video game bosses, especially when they pose a huge threat to our adventure. However, there have been cases where certain video game villains have left us to ponder who the real monster is. In fact, some games are so effective at toying with our emotions that we end up growing attached to them, to the point that we feel guilty for beating our virtual foes. Join us as we take a look at 10 video game bosses that still fill us with remorse to this day. Please be aware there will be major spoilers for each of the games discussed below.

Sif the Great Grey Wolf (Dark Souls)

Sif was the wolf companion of Sir Artorias, the Abysswalker and after his owner passed away, the loyal wolf became the sole guardian of Artorias' grave in the Darkroot Garden. The lore behind Sif becomes even sadder when we learn that Artorias sacrificed himself to protect Sif from the murderous creatures of the Abyss. It’s clear that Sif doesn’t want anyone to disturb Artorias’ resting place and the Great Grey Wolf proudly wields Artorias’ greatsword to cutdown those that dare trespass.

The fight certainly makes for a rather harrowing experience, especially when you see the Great Grey Wolf limping and whimpering near the end of the battle. Sadly, the heartbreak doesn’t end there. If you play Dark Souls’ additional content you have the opportunity to see Sif once again, however, this time you will find a young and frightened Sif lying under Artorias’ protective barrier. Once you save Sif from the Humanity Phantoms, you’ll be rewarded with Artorias’ Cleansing Greatshield and an alternate cutscene. Upon entering Artorias’ resting place Sif will now recognise you as its saviour and appears reluctant to fight. Unfortunately, Sif remains loyal to Artorias to the bitter end, making this fight a hollow victory with many a tear shed.

The Colossi (Shadow of the Colossus)

Team Ico’s Shadow of the Colossus tasks the player with slaying 16 monolithic creatures in order to resurrect a girl named Mono. It’s a rather simple premise and it doesn’t sound too dissimilar to the countless hero saves princess stories we’ve seen and heard countless times before. However, Shadow of the Colossus is memorable due to the guilt it makes us feel when we slay each colossi. The game plays hauntingly sad music when you kill a boss and then forces you to watch its lifeless body crash down into the ground below. You quickly realise that most of these ancient creatures don’t attack you until you clamber up their gigantic limbs and start hacking away. As a result, almost every victory over the 16 colossi feels hollow and burdensome.

This burden is even reflected in the protagonist Wander. Over the course of the game, his appearance begins to change as he continues on his colossi killing spree. His clothes will become dirtier, his skin paler, his hair will darken, and markings will appear on his body. He also begins to grow a small but notable pair of horns atop his head. Wander’s gradual transformation continues to raise our suspicions of our role in this tale, but we continue to slay each colossi with the hope of saving Mono. Unfortunately, our suspicions are confirmed at the end of the game, as we find out the colossi were all innocent, and there death was all a plot by the evil Dormin to recover the fragments of his former self. We didn’t just kill innocent and beautiful creatures, we also willingly carried out Dormin’s evil deeds.

The Boss (Metal Gear Solid: Snake Eater)

The fight against The Boss in Metal Gear Solid: Snake Eater is arguably one of the most emotional moments in the series. The game’s ending sees Naked Snake reluctantly face off against his mentor The Boss, with the orders to kill her for defecting to the Soviet Union. A tense battle of cat and mouse pursues in a beautiful field of white flowers, which tasks the player to rely on their hearing and superior mechanics to outgun their camouflaged foe. The lengthy fight comes to an end and the player is forced to kill Snake’s unarmed mentor.

It’s only after spending the night with Eva that we learn The Boss was not a traitor, but a spy deployed deep within Volgin's ranks in order to help the U.S. secure custody of the Philosopher's Legacy. By allowing herself to be killed by Snake, The Boss ensured America’s innocence, but also sacrificed her legacy as hero. Sadly, only Snake and a handful of others know of her heroic sacrifice, but we’ll always remember the true hero of the Metal Gear Solid franchise.

Saren Arterius (Mass Effect)

The rogue Spectre agent Saren Arterius has little regard for life, while his disdain for human expansion into Citadel space sees the Turian veteran embarking on a quest to overthrow the Council and allow Reapers to invade the galaxy. During our time with Mass Effect we end up pursuing Saren across many planets until we meet the rogue Spectre agent upon the Citadel. Depending on your dialogue choices, you can either convince Saren that, indoctrinated or not, he still has a way to stop Sovereign. If you choose this option, Saren will commit suicide by shooting himself in the head, to prevent himself from opening the Citadel relay, but not before muttering, “Goodbye, Shepard. Thank you." Saren definitely had warped beliefs when it came to saving the universe, but he did gain our respect with his final act of bravery.

Asriel Dreemurr (Undertale)

Undertale is rife with sad boss fights but Asriel Dreemurr forces the player to call their friend's souls, which are inside Asriel. These friends appear as Lost Souls, and the player must defeat them by reminding them of who they were. After the protagonist manages to save all the Lost Souls, Asriel's compassion returns to him, and he begins crying. Once the fight is over he breaks the barrier and returns everyone’s souls back to them. You can’t help but feel bit bad for the little guy, especially when he’s sobbing his eyes out in front of you.

Maiden Astraea (Demon’s Souls)

Demon’s Souls features some truly beastly bosses, but not all of them play out the way we imagined. One of the most memorable bosses from Demon’s Souls also happens to be one of the saddest encounters in the game. When you enter a boss fog in the Souls series, you’re usually met with some demonic beast who wants to rip you apart, but Maiden Astraea poses no threat to the player. Instead she plays with our morality.
Upon entering the depths of Astrae’s sanctuary, she’ll politely ask you to leave stating that “there is nothing here for you to pillage or plunder. Please, leave quietly.” Her bodyguard Garl Vineland will try and stop you from attacking her, but once you strike him down the Maiden acknowledges her defeat. If you talk to her after killing her loyal knight, she will simply commit suicide, telling you that she can no longer defend herself and that you can have your precious Demon's Soul. This is definitely one boss that still has us feeling guilty to this day.

Steve Burnside (Resident Evil: Code Veronica)

Steve Burnside’s tale is certainly one of the most tragic in Resident Evil history and he ends up having a rough old time in Code Veronica. Protagonist Claire Redfield meets Steve many times throughout her stay on Rockfort Island and he constantly helps her survive multiple ordeals. We eventually learn that Steve was sent to Rockfort Island prison along with his father, due to his father selling Umbrella Corporation secrets at auction. To make matters worse, Steve is later captured by Steve and Alexia and is injected with the T-Veronica virus, which mutates him into a disgusting monster.

Steve attempts to then lop off Claire’s head with an axe, but he regains control of his body and manages to free Claire from Alexia’s tentacles. Even though we didn’t kill him directly, we still feel bad for not being able to save poor Steve. His cheesy voice acting and tragic death will never be forgotten.

Marlene (The Last of Us)

While Marlene is not a boss, we still feel a little bad for the leader of the Fireflies After all, Marlene believes that Ellie’s immunity to the virus could lead to the development of a vaccine that could save humanity. Unfortunately, performing the surgery would prove fatal. However, Marlene sees Ellie’s sacrifice as a necessary evil and one which could potentially save countless lives.

Thankfully, Joel stops the surgery and kills Marlene to stop her coming after them, but her death is still a controversial talking point among fans. To many she will remain a ruthless commander willing to sacrifice a young girl’s life, while others believe she was a brave leader who was prepared to make hard choices in order to save humanity. Either way, Joel pulling the trigger was as satisfying as it was sad.

Vaas (Far Cry 3)

Honestly, Vaas is the only thing we really remember from our time spent playing through Far Cry 3. That’s not to say the game is bad, it’s just that his impact on the story was so big. Vaas wasn’t even the main antagonist in the game, but his loud nature and psychopathic tendencies made him one of the most interesting, yet terrifying characters we’ve seen from the series since. Even though Vaas was a terrible person, we couldn’t help but feel a little disappointed after the pirate leader was killed off hallway through the game. He stole the show in every scene he appeared in and once we beat Vaas the game was pretty much over.

Jen (Prey 2006)

Prey sees protagonist Tommy Tawodi along with his grandfather Enisi and girlfriend Jen abducted aboard an alien spaceship, referred to as The Sphere. After Tommy’s grandfather is killed, we are tasked with rescuing his girlfriend, but tragedy strikes when Jen is found alive in a strange looking pod. It turns out Jen’s torso has been surgically grafted into a monstrous alien. Unfortunately, Jen is unable to control the creature so Tommy is forced to kill her. Thankfully, it’s not all doom and gloom for Tommy as he manages to spirit Jen away to The Land of The Ancients, where she is seen with Enisi at the end of the game. This was one fight we’re glad had a somewhat happy ending.

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