50 Years of Boss Fights: Video Game Legends

Introduction

I’ve always loved bosses, ever since I first ran into Doctor Robotnik in the SEGA Master System version of Sonic 1, way back in the early 1990s.

The scrolling screen powered by ‘blast processing’ would lock in place, the music would change, and you would have to figure out how to beat him. And even when you did win the fight, he’d keep appearing in different ways to keep challenging you, culminating in his Final Boss form — something that’s still occurring today with the latest Sonic entries.

At four years old, this led me to have a constant, low-level excited fear of what could be next to face off against. And it continued once the Sony PlayStation arrived — games such as Tekken and Ridge Racer made sure that bosses were an event, and they’d each be more challenging than the last one. Bosses expanded to not just being an end of game challenge — they became something more, something more fun than even the games themselves for some players.

Over 30 years have passed since then, and bosses have become the main focus of certain games, such as Elden Ring. The grandness and the challenge of them can be sadistic, especially as you’ll have seen the ‘You Have Died’ screen repeatedly, but these games have a certain charm where it’s fun to get that screen. It drives you to restart and approach them with a better strategy, which, in my opinion, has only reinforced how important bosses are.

It wasn’t until after my first book, The Making of Tomb Raider, launched in October 2021 that work really began on this project. While there are 51 bosses to read after this chapter, I’ve most likely played triple that, to see which ones are the most memorable, the most fun, and the ones that helped to redefine what a boss can be across generations.

During the making of this book, some bosses have been replaced, some have been revisited, and some feature interviews with the developers involved in the bosses, to better understand why these games and bosses turned out to be the way they became.

I also wanted each boss to show you what a game could be capable of — from unwinnable bosses to those that can only be fought through pressing a series of signposted buttons, usually called Quick Time Events (QTE).

A boss is more than reaching the end of the stage these days — it’s evolved to something where it can be an event, a moment that drives the narrative and keeps you engaged in the story and the characters you’ve been controlling so far.

I also think that bosses in games can reflect our superiors in real life that we’ve dealt with in the past — they could be in our jobs, in relationships, and even our pets. We’ve seen when they get annoyed and angry, and we can change our approach to defend our corner.

It could be situations surrounding a pay rise, an argument, or if a pet suddenly does a ‘zoomie’ moment where he’s running around like a madman and almost knocks some important objects over, as our dog Jolly once did.

Our imaginations run wild and we dream up situations of gaining the upper hand in these scenarios, inspired by boss fights that we have previously played — I have certainly had those thoughts across the years.

We’ve all approached bosses for most of our lives without knowing it — but it’s how we deal with them, and how we work with them in other situations, which allows us to succeed and win them over to our corner.

With video games, that feeling of fighting our corner is only exemplified by the worlds that the characters inhabit — that you reach a point where you almost feel ready to take on something harder, but there are some bosses out there that really stand out from the pack in memorable ways.

Granted, there’ll most likely be a boss or a game that you think should have deserved a place here. However, this list is relative — it’s one that honours the bosses that came before, as well as delving into the moment that arguably began the boss fight tradition way back in 1974.

There will almost certainly be some games that you will have never played before — whether it’s because it was before your time, or you never had the opportunity to own the console or handheld to play it. Of course, it could be harder due to licensing rights if the game can only be played on the system it was originally released on. Sonic 3 was a great example of this for years, until it was unveiled as part of the Sonic Origins compilation in 2022.

What I will say for the games in this book is that you should look for them to play as best you can. Read about them, learn why I chose them, and then make it a mission to find them to play one weekend. It’s like trying new foods from different cultures — you won’t know how they’ll make you feel until you give it a try.

So while the first boss after this is also an introduction to what began the ‘boss fight’ from 50 years ago, mostly told from the proprietors themselves, the remaining 50 bosses follow the same structure that all tell a story of what the bosses are, why they’re still so memorable, and why they need to be played at the earliest opportunity.

I hope after reading this book, you’ll go forth and try to play almost all of these bosses, and then wonder what a boss fight could be capable of in the next 50 years. It could entail VR, AR, AI and anything else that is nothing more than a concept at this point.

For me, I can’t wait to see what else developers and players like you can come up with, so they can, again, make an impact on a young child who first encounters a boss battle, setting them on a path to fight their corner — whether that be in words, art, protests or anything else that they believe in.

Golden Dragon — DND (1974)

In order to look at the memorable bosses in gaming, we need to look back at what is considered the first ever boss in a video game, while having its two creators tell the story of how it came to be.

In 1974, two individuals created a game inspired by Dungeons & Dragons, the massively popular tabletop role-playing game, with this virtual version able to be played on a PLATO computer system.

This game, known as simply DND, housed an event for the player that made them face a dragon — this was to unofficially be the first boss in a game, ever.

The game is in orange and black, a standard for the PLATO operating system, and there would be no music — this would be where your imagination would kick into action, helping you to form the sounds and images of just what this Golden Dragon would do once you approached it for battle.

Gary Whisenhunt and Ray Wood first met as students, in a library at Southern Illinois University back in 1974, and both remember it clearly.

Wood kicks the story off for us, saying, "To go all the way back: there was a PLATO terminal on the first floor of Morris Library at SIU in Carbondale. One day, I looked in and there were a bunch of students huddled around it… probably six or so. So, I got permission to use the system and log on, and I began playing around with it. The room was about eight by eight metres. In order to see the screen, the lights were turned off.

"You could only sign up for one hour a day. Whenever you used the terminal, two or three or more people would show up and sit in the room with you. Sometimes we would just shoot the sh*t, or just talk about the programs. There was a group of maybe 10 people who regularly used PLATO, so we got to know each other.

"There were some games on it… MoonWar, Dogfight, and a few others. The PLATO rules were that you could only play games during ‘non-business’ hours — which was after 7pm and before 7am Monday through Friday. Also, games were given a low priority…so, users playing games were the first ones kicked off the system in times of heavy use.

"For some reason, Gary Whisenhunt and I hit it off, and we developed a friendship, which still continues. I think the reason we get along is because we had interests outside of computers and engineering.

"One day, a new game called PEDIT5 (written by Rusty Rutherford) became popular. PEDIT5, in modern lingo, is a God’s eye view dungeon crawl."

Whisenhunt takes over the story now, remembering the very first time he found that fateful computer: "Sometime in the fall of 1973 or the summer of 1974, I discovered the one PLATO terminal at the university. It was housed in the basement of the library — not many people knew of it and it was more of an interesting oddity than something that was being used for actually teaching anything.

"I was fascinated by it. I had always excelled at Math, but had never actually interacted with a computer — which were pretty rare prior to any type of personal computers existing. Beyond that, PLATO was way ahead of its time, and represented what it would take many years for mainstream computing to accomplish — graphical interfaces, multimedia, interactive communication, touch screens, and more.

"I started playing with the PLATO terminal and taught myself how to program it. The thought of creating a program was actually kind of exotic at the time.

"The PLATO terminal was housed in a small room and you could sign up for time in one-hour blocks, no more than one hour a day. There were several other students there who were also intrigued by PLATO as well — people would often hang around the room looking for extra free time as I sometimes did. One of those people was Ray Wood. He and I became good friends.

"Of course, given the graphical and interactive nature of the PLATO system, it was a great platform for games. Games were generally frowned upon, especially up at the PLATO home at the University of Illinois. However, the system was perfect for gaming and of course people started writing them. Several of us in Southern Illinois University would sometimes play some of these games: Airfight, Empire, etc. Around that time, there was a dungeon game called PEDIT5 which had been created. Ray and I had played that, it was loosely based on similar concepts of the Dungeons & Dragons paper game that had recently come out.

"However, PEDIT5 would occasionally be deleted — games were seen as an illicit use of the PLATO computer in some places. Ray and I had done some PLATO programming before that, but had never written a game — no one at Southern Illinois had ever written a game. We decided that we should try and write our own dungeon game, and we were pretty sure that it wouldn’t get deleted because the person that oversaw the PLATO terminal really knew nothing about it and it was just something else he was supposed to manage. He’d never even know of its existence. So Ray and I set about writing the game. We would meet at different places when we had open times between classes — usually on the steps of the library, weather permitting. We would talk about what we wanted to accomplish and how the game would work. Then we would kind of divide up the programming tasks and each spend our allotted time on the one terminal to enter and debug the code."

Wood picks up the thread again here: "The problem with PEDIT5 is that you couldn’t play it during ‘work’ hours. So, all the guys at SIU complained about it. The other thing, which is going to sound crazy to people now, is that the university admins thought games were a waste of valuable computer time, and thus would regularly delete the game from the system. So, it would disappear for weeks at a time.

"Being the devious college students we were, Gary and I became the system administrators for the SIU Plato site. Thus, we were in control of the programming space at SIU. So, no one could delete computer programs but us.

"Anyway, Gary and I decided we would write our own dungeon crawl. Since we were SysAdmins, the game wouldn’t be deleted, we could play the game during normal hours, and all the guys at SIU could play the game whenever they wanted. So, everyone was happy.

So, we started writing a version of PEDIT5.

"PEDIT5 had some severe limitations. The biggest one was that a user couldn’t save a game. If you logged off PLATO or were kicked out of PEDIT5, your game disappeared. You had to restart from the beginning. So, no matter what items you found in the dungeon, they always disappeared in a few hours. None of that seemed particularly fair.

Wood wants to stress an important point, for the record, at this moment in the story: "Gary and I worked together. DND was a joint creation."

Wood continues: "Since at SIU we were limited to one hour on PLATO, the first thing Gary and I implemented was a SAVE GAME function so you could return to the game without losing your gold, weapons and levels. This made the game an actual RPG (Role Playing Game). In some ways, the save function made DND the very first real RPG.

"We had some fun with the game, trying to introduce some cheeky humour into it. We even patterned one of the monsters in the dungeon after a particularly obnoxious student.

"In order to program better, Gary and I would try to sign up for PLATO so that our times were next to each other. That way, we had a block of two hours to work on it together. We usually did it on Saturday morning. We would show up at the library and go to work.

One Saturday after we finished programming, we decided to go out for a burger at a local greasy spoon. It was next to the train station in downtown Carbondale. They had a couple of pinball machine games there, so we started playing them.

"The pinball machines had a high score function. If you had one of the top 10 scores, you could enter your initials.

"Gary and I started playing. Gary, being the guy with good eye-hand coordination, got a high score. I started playing, and unbelievably, I beat Gary and got the top score. This was the first and only time I ever got a high score on a pinball game. I was, to be honest, pretty excited.

"Gary and I started talking about how neat it would be to have a high score for DND where people could put in their name. But, the question came up, ‘What does a high score mean in a video game?’

"Because DND had a save game function, a person could simply play the game and get a new high score every time s/he played. So, it wouldn’t have any meaning.

We said, ‘What if we put an ending on the game, you know, where the game stopped?’ If a player ends the game, then he gets to put his high score up, but his character gets deleted. We came up with the idea of the players going into the Elysian Fields, the mythical place where Roman heroes resided after their death."

Wood highlights a second important point here: No video game in existence ended other than by the player getting killed or quitting.

Wood adds: "All other video games, the difficulty of the game increased until it was impossible to proceed further. The player would always ‘lose’. Take PONG… if you play single player, it gets so fast that no one can keep up. That is the way all the video games were prior to DND.

Once we came up with the idea that the game would have a planned ending, the game changed. If there is a clear ending to a game, then ‘why’ would a character play the game? If you are not going in simply to kill monsters and accumulate gold, then why do it? So, we decided that a player venturing into the dungeon must be on a quest to recover ‘The Orb’ (a MacGuffin, as Alfred Hitchcock would say)."

Whisenhunt picks up the story at this point, saying, "While DND was a part of the Dungeons & Dragons genre, we had our own take on it. It had humour and was somewhat a tongue-in-cheek implementation of Dungeons & Dragons. Early versions — which some might call ‘alpha’ versions of the game — started being played at Southern Illinois and word spread to the University of Illinois and people began playing here. It was very popular. I had picked the name to be DND because when many people were saying ‘D and D’ it pretty much sounded that way.

"At some point early on, one of the things that we decided that we wanted to do is to give some goal for the game in PEDIT5 you wandered around and did stuff, but there was no endgame. On top of that, PEDIT5 had few characters that it could store. We had enough for everyone, and we decided that there needed to be a quest so to speak — a purpose. So we created The Orb, a great sphere for which someone should try to find and take out of the dungeon. The name for The Orb was inspired by the recent Woody Allen movie, Sleeper, which has a scene where there is an ‘Orb’ passed around and whoever touches it gets aroused. The scene is pretty funny.

So then we decided that we needed a special monster to guard The Orb, something that was extremely difficult to defeat and only a character with lots of experience and collected stuff had a chance. Even then, we wanted there to be a fair chance that even the most powerful might fail, because if you got The Orb and got out your character was retired to the Elysian Fields — kind of a hall of fame. Everyone who played the game could see the characters that made it to the hall of fame (and essentially ‘won’ the game). It was difficult enough that even Ray and I, knowing how everything worked, would have to work hard and still might fail to win the game. We also added many more levels to the dungeon and a few more monsters and treasures and pretty much released the game.

The game began to spread to other campuses, including the University of Illinois, which was hours away from Southern Illinois University where Wood and Whisenhunt had made the game. Whisenhunt remembers: "After this, it had become quite well known at the University of Illinois, where there were many terminals, and there were many people playing it. I think in the first few months there were over 100K game plays. While in today’s world, that doesn’t seem like a lot, but on a system that probably had a very limited number of terminals, and those terminals being chiefly used for academics, 100K was a lot. We were kind of pleasantly shocked. However, we started noticing that there seemed to be more people defeating the dragon, grabbing The Orb and exiting to the Elysian Fields, than we thought possible. We thought there must be some game flaw, something we overlooked. So I made a trip up to the University of Illinois in Urbana, IL for a weekend. It was a three and a half hour car trip. I was a poor college student so I camped at a rest stop on the interstate highway there overnight — which is now likely to get you arrested.

"So I went to the PLATO classroom on a Saturday night — dozens of terminals there and just wandered around and casually looked to see if people were playing DND. There were several. What it turned out that they were doing, indeed, was something that we had never thought of. They were stepping into the first part of the dungeon, taking a few steps around until they happened to encounter some monster, easily defeating it, and exiting back out. The strength or capabilities of the monsters was based on where you were in the dungeon, and at the very start, they were pretty simple to beat, particularly for a character with lots of experience, strength, etc. So these guys would do this little go in, kill something, then exit. Repeat for hours on end, and perhaps over several days.

"So that was the design error, we had never thought that anyone would spend that amount of time doing something rote and tedious. Boy were we ever wrong. So we changed the design of how the monsters worked. Attack factors, as Ray called them. We made it so that monsters of greater strength, i.e. more deadly, were attracted to how much gold you had accumulated. But this was based on a smaller random chance. However it meant that the longer you were in the game, the greater probability that you would get attacked by a monster with strength comparable to yours. If you just went in and out over and over again, you spent more time in the dungeon than if you explored lower levels and had to defeat more powerful creatures and found larger treasures. Since The Orb was the most valuable treasure, if you were carrying it, powerful creatures were very interested in you.

"The first few people to encounter this were surprised and they would post about it on the DND notes file (a notes file on PLATO was the equivalent of an internet forum or Reddit today). One such person wrote a poem about it, about how his long standing character