The Context: After what initially seemed to be the final fight of the game, Snake - and Meryl depending on if you met the requirements for the good ending or not - gets in a jeep and begin escaping Shadow Moses through an underground tunnel, but not before Liquid storms onto the scene with a jeep of his own. The Fight: This isn't a traditional boss battle by any means; Liquid actually doesn't even have a health bar. Instead, this is mostly a cinematic resolution to the game, but also one of the first cinematic moments of its kind for the gaming industry. It's literally just an on-rails segment where Snake must operate a machine gun turret and endlessly fire at Liquid until the ending of the tunnel is reached, kicking in the game's ending. The death of Liquid himself however, is one of the franchise's most iconic and revered moments; ("Fox....die?!") so despite the simplicity of the fight itself, it does get bumped up a notch.
28. Olga Metal Gear Solid 2
The Context: Snake encounters Olga on the observation deck of the game's opening Tanker chapter, and while she is a complex character, it's not something that is brought out early on. At this point she's just the daughter of a Russian general that Snake is here to stop. The Fight: Despite being a glorified tutorial for many of the game's mechanics and a prelude of the multi-layered fights to come, this fight actually has some depth to it. With a waist-high barricade and assortment of objects obstructing the way forward, Snake must play a bit of cat and mouse with Olga and actively shoot things in the environment - like extremely bright lights and tarps - allowing himself a view to get some tranquilliser shots off. When Olga is in the open the fight is pretty straightforward, but creating your shot is filled with interesting little tricks and actually grows in its complexity on harder difficulties.
27. Ocelot Metal Gear Solid 3
The Context: Before Ocelot was a God at twirling revolvers and marksmanship he was a green rookie in search of the weapon that would suit his preference for combat. He and Big Boss have their first of many encounters throughout the franchise early on in Metal Gear Solid 3, at a mountainous area with a crevice separating the two combatants. The Fight: Everything mentioned about the Olga fight from MGS2 can be applied here; it's a fairly straightforward fight with a purpose to ease you into the combat of the game. It's really just about picking your spots of cover wisely and firing bullets whenever an opportunity arises. Perhaps what's even more fascinating than this being the fight where Ocelot becomes the revolver aficionado we are familiar with, is the fact that while he is unconscious afterwards, you can kill him which results in a hilarious game over message stating that you have caused a time paradox in the events of the franchise.