Dragon Slayer Ornstein and Executioner Smough (Dark Souls)
Right, Dark Souls. You all know it for being one of the most difficult games of the decade so far, and this fight is (arguably) the reason why. Until now, players have faced all manor of monsters, and even a few groups of enemies, but this was the first fight where two very difficult enemies, who attacked at once, had wildly different strategies to defeating them. Focusing on Ornstein meant the much larger Smough would come from off-screen and turn you into paste; chipping away at the slower Smough’s health was a invitation for Ornstein to spear you from behind. Once you did finish off one, the other would fully heal and become far more powerful, so it was unwise to try and split your damage output.
Defeating the two was possible via a few options; summoning either AI or player controlled help to divide their attention was the most common, but where is the fun in that? Adding to the dilemma is the items they drop, each depending on the order they were defeated; so if you did want a certain reward, you’d have to hope your allies cut them down in the correct order. Attempting to keep hem both on screen at the same time was the “purist” way to do things, and in my opinion definitely the most rewarding.
Once these two guardians were defeated, the entire second half of the game opened up to you. These two guardians are widely discussed in the Dark Souls fan-base, due to Ornstein (or a very similar enemy) appearing later in the sequel. Although considering what’s going on, and who’s in charge, behind the scenes of the city these two lovable scamps are fought in, who is to say either of them are real at all?
Pokemon Trainer Red (Pokemon Gold/Silver/Crystal)
Last, but absolutely not least, we come to the oldest entry on the list, and potentially the most unexpected. I would have been 9 or 10 when I finally climbed the slopes of Mt Silver, entered a dark cavern and saw a lone trainer standing at the end of the tunnel. It took trawling through two regions, eight Gym leaders, the Elite Four and a Pokemon Champion to even be allowed entry into the area of this mountain, so imagine my reaction when the final opponent just so happens to be the player character from the previous generation of games, making this one of very few games I can think of that hold this honour.
Leading the charge is Red’s Pikachu (obviously a reference to the Pokemon anime, and the Pokemon Yellow adaption), which at level 81 is the highest leveled opposing Pokemon you’ll find in the game (and if we go by the remakes, it’s level 88 AND has the item which doubles it’s speed and attack!). Also on his team are fully evolved versions of every starter from the previous games, each of which alone could cause real problems. Ideally your team would be strong enough to defeat him by now, but if it’s not, this contest can quickly become very one sided.
So these may not be categorically the best boss battles in gaming, but as far as challenging, meaningful and, above all, memorable moments go, these are my personal favourite five. If I’ve forgotten any obvious ones, or there are any you think I should check out then let me know!