RANKED! The 10 Most Challenging Bosses In '90s Video Games

Photo: Midway Games

Video games have long been an entertaining way to spend our time. They’ve provided countless hours of joy while we’ve burned away our brain cells, become mindless zombies or whatever other lame side effect our parents say these games cause.

But with all the happy moments, there have been some frustrating ones, and these have mostly occurred when faced with one of the many bosses we’ve fought in these games. In particular, ’90s video games produced some of the most, infuriating, irritating, aggravating and downright emotionally taxing challenges from bosses. These characters caused property damage in excess of billions (probably) as a result of game controllers being thrown vigorously across the room. They also caused us to lie to our parents about where all our allowance went, explaining that the school bully beat us down for it when really we dropped it all in quarters at the local arcade.

More Nostalgia: ’90s Music Videos That Explain Why We’re Like This Now

Yeah, the ’90s was full of video-game bosses that humbled us. Some we overcame after hours (years?) of attempts, and others remain undefeated. Let’s take a look back at the bosses that caused the gray hairs we have today (click on the “+” icon to read our takes)

90s video games

10. Bowser, Super Mario 64

You’ve all faced Bowser before and he’s been pretty tough. But there was a whole new level of anger we reached when we fought him in Super Mario 64. Since this was the first time we saw Mario in the 3D world, it’s also the first time we had to work our way around an environment to win. Throwing Bowser into waiting bombs was never anything we had to do before, and trying to accurately toss him around to beat the game was a challenge met with furious rage. Whatever happened to just running under him and touching the glowing ax that pulled the bridge out from under him?
9. Magneto, X-Men (arcade)

How much money did you carry to the arcade? If you didn’t have at least $10 in funds dedicated to X-Men, you needed to use a payphone to call your mom and ask her for more cash because you weren’t going to beat Magneto. The master of magnet wasn’t exactly fast or difficult to hit. No, it was more about the amount of times you had to hit this jerk. When he threw his shield up, all hope was lost and you had to survive until he was vulnerable again. What a metallic pain in the ass.
8. M. Bison, Street Fighter II (arcade)

Street Fighter II is arguably the greatest arcade game of all time. And if not that, it was the one most widely known for bringing us back to the arcades on a regular basis. Despite this, the four bosses were seemingly impossible to beat, and none were more difficult than the final boss, M. Bison. This guy flew across the screen like a damn torpedo and jumped off your head just to mess with you. In the end, it all came down to timing with Bison, knowing the right moment to strike while at the same time keeping the pressure on. Before you figured this out, though, you were dipping into your X-Men fund to beat this guy.
7. Goro, Mortal Kombat

Goro wasn’t even the final boss in the original Mortal Kombat, but he sure as hell felt like it. This ugly, four-armed bastard fell down from the ceiling, threw you around, and hit you hard enough to drain a ton of your power. To make it worse, he flexed for the camera in the middle of fights like a truly vain a-hole who knows he has you beat. After finally beating Goro, you welcomed Shang Tsung with a sense of relief (unless he morphed into Goro, which ultimately upset you all over again).
6. Alien Brain, Super Contra 3: Alien Wars

Remember how excited you were when Contra came to the Super Nintendo? Remember how quickly that excitement dried up after you finally faced Alien Brain, the final boss, and he just took you out like nothing? Yeah, this thing was a buzzkill like nothing you’d seen in the previous two Contras and no amount of up, up, down, down, left, right, left, right, B, A was going to curb your frustration. As with all side-scrolling games, you had to figure out the timing and precise movements in order to take this ugly thing down. Even worse, you had to do it three times because it took on a different form after you beat it, finishing off with an armored crab-looking beast while you hung from a helicopter. The anxiety felt while fighting this boss is rivaled by very few.
5. Shredder, Teenage Mutant Ninja Turtles (arcade)

More and more quarters spent on an afternoon of trying to beat a boss that seemed to have a little too much of an advantage. The Shredder was the final boss in the Teenage Mutant Ninja Turtles arcade game and, like Magneto in X-Men, cost us a bunch of money due to the seemingly endless amount of change we shoved into this machine. Truth be told, I cheated to beat this game. I let some other kids play the entire game in hopes they would get frustrated with Shredder and just give up. Luckily for me, they did just that, and I fed my quarter to the machine to continue their game and beat an already damaged Shredder. I walked out of the arcade a hero that day and I don’t care what you think of my strategy. I beat Shredder.
4. Shao Kahn, Mortal Kombat 2

There is nothing more annoying that some roided out underworld menace who walks around in his underwear and shoulder checks you into oblivion. This, boys and girls, is Shao Kahn. After beating what can only be described as Goro’s weaker cousin in Kintaro, you fight Shao Kahn and deal with his incessant shoulder checks and an occasional spear chucking. If he hits you four times, you’re done, which is really lame considering his go-to move is something reject offensive lineman do before they get cut from a football team. As you might imagine, this cost us dearly on the quarter front and made us toss up our hands before heading over to play The Simpsons arcade game.
3. Emerald Weapon, Final Fantasy VII

It’s extremely rare that a boss you encounter in the middle of a game is harder to beat than the final boss. This is the case with Emerald Weapon in Final Fantasy VII. You encounter it at the bottom of the sea while you’re cruising around in a submarine. Af first it looks harmless, but then you graze it with your sub and all hell breaks loose. Truth be told, I never beat Emerald Weapon, and I no longer have a desire to find out if grown-up me has what it takes to beat this super boss. But if you want to have your hand at it, by all means take your shot. The video above is valuable in your efforts.
2. Dracula, Castlevania III: Dracula’s Curse

This game literally had my mom threatening to take my Nintendo away if I didn’t stop yelling in frustration. In Castlevania III: Dracula’s Curse, you of course fight Dracula as the final boss. He lifts flames from the floor, shifts to different spots on the screen and keeps you guessing where you should stand next to hit him with your whip. When you finally get past that you think you’re in the clear, but he then turns into some weird-looking monster with a melting face that floats around and drops his nasty goop all over the place. Once you beat that thing, you fight a giant gargoyle statue that shoots lasers at you while the floor decides it doesn’t want to be a floor anymore and floats out from under you. He’s just supposed to be a vampire, but he hits you with three times the irritation and basically humbles you into rethinking your gaming purchases. I got this far in the game and just gave up, eventually trading up my NES for an SNES, never to give Dracula my time of day again… until the SNES Castlevania came out.
1. Psycho Mantis, Metal Gear Solid

Beating Psycho Mantis doesn’t just take skill, it takes you adjusting your hardware outside of the game. In one of the most mind-blowing moments of video game history, the player must figure out that they must remove their controller from Port 1 and insert it into Port 2. This prevents Psycho Mantis from reading your memory card. If you don’t do this, you’re screwed and you he’ll continue to own you as he reads how far you’ve gotten in Crash Bandicoot. This blew gamers away when we discovered this because of its unorthodox approach. It’s not like we had Google back then to look up how we could beat the game; we actually had to figure out this stuff on our own. What an incredibly sneaky move by the game’s developers. Kudos.