The hardest, meanest, and most challenging game enemies...

Toughest Video Game Bosses

Here’s a list of what I consider to be some of the toughest video game bosses in modern history. There are plenty of game bosses that are not listed, but these all came to mind fairly quickly.

Toughest video game bosses

Hitler, Wolfenstein 3D, PC
It’s impossible to sneak up behind this mechanized tyrant because he always faces you—something the designers implemented intentionally. Your best bet is to utilize the pillars for cover while keeping your chaingun screaming. Speaking of chainguns, he’s got four of them simultaneously flying through ammo—nice. An exhausting battle to be sure, with an ending that was worth every calorie burned. Who can forget the slow-motion death cam replay once he capitulated to your inferior weaponry. I can still hear him gasping, with his last digitized breath, “Eva…auf wiedersehen.”

General Raam toughest boss

General Raam, Gears of War, Xbox 360 (“Insane” on single-player)
What makes the General Raam boss battle remarkably challenging is facing him on “Insane” difficulty, within the single-player campaign (which is how I beat him). It’s not unreasonably hard on a lesser difficulty, and even on “Insane” it’s considerably easier within cooperative mode.

The final confrontation takes place on a speeding railcar, and I consider it to be one of the cooler, most visually-stunning boss battlegrounds in history. He begins by casually walking towards you from a distance, shrouded in a protective cloud of bats, which essentially shield him from anything but a well-thrown grenade. His oversized-machine gun blazes often, but periodically he’ll send the aforementioned bats to attack (which makes him vulnerable to your weaponry), at which point you must leave cover and seize the opportunity to get a torque-bow shot off—a headshot with active reload is key. If you can’t destroy him by the time he approaches your immediate vicinity, you’ve got to run the opposite way and put some distance between the two of you. Here’s something many players don’t realize: there’s a gargantuan turret on the far end of the railcar—one that can be used to make short work of Raam—the trick is getting there in one piece.

Akrid wasp toughest bosses

Giant Wasp Akrid, Lost Planet, Xbox 360
It’s not overtly difficult to damage the wasp akrid early on, but as soon as you get its power down to around 50%, it goes berserk! Not only does it begin moving much faster, but this coincidentally is usually about the time you need a new mech. If you’re unlucky enough to find yourself running around on foot, rest assured, you will be repeatedly pummeled by projectiles, making it almost impossible to gain a footing. Is it too much to ask that I be able to at least turn around before I get repeatedly drilled again? My internal dialogue was literally: “Could this be it? I have to stop playing already? This can’t be happening.” Finally, after trying for what seemed like forever, I tore that flying mutant a new one. What I later learned is that there is a hive in the back of the map that you can destroy, making beating this boss quite a bit easier, but still difficult. I unknowingly did it the ultra hard way. Yaaaaaay ME!

Mike Tyson toughest game boss

Mike Tyson, Mike Tyson’s Punchout, NES
Bordering on the laughable, Tyson can end the fight with one lightning-fast punch, and blocking…well…it’s completely and utterly useless. The funny thing is, it’s easy to start thinking you’re pretty good as you fly through the different pugilists in the game—the problem is, each of them is a cake-walk when compared to Iron Mike. In other words, you end up over-confident and under-prepared for the final fight. Immediately after you get inevitably pummeled, you think, “What just happened?” Sure he’s got a pattern just like every other fighter, but his punches are infinitely stronger, and his movements are immeasurably faster. He requires flawlessness.

Motaro toughest video game boss

Motaro, Mortal Kombat III, Sega Genesis
One of the more unique sub-bosses in the Mortal Kombat series, the centaur Motaro proved to be my arch-nemesis. I would rather go up against any other character, hands-down. Ok, so he can shoot fireballs from his metallic tail—annoying, but I can deal with it. He can teleport back-and-forth in rapid succession, even behind you, at which time he usually tries to either grab you and toss you (unblockable) for an inordinate amount of damage, or he’ll kick you across the screen with his back hooves—ok, getting angrier. Did I mention projectiles are entirely ineffective on him? So, you essentially have to defeat him without using your special moves (Sub Zero’s ice move, for example). To cap it off, your projectiles will almost certainly be deflected back at your character, resulting in self-inflicted damage—cheap! Motaro’s roars are demented, and I think it psychologically makes him seem more imposing. In the end, I despise him.

Akrid spider Lost Planet game boss

Spider Akrid, Lost Planet, Xbox 360
The Spider Akrid is a mystery to me. I’m not sure if it was extraordinarily tough, or I just had way too little thermal energy when I faced it (2,400). Either way, I eventually sent this giant peckerwood packing. One of the most frustrating aspects of Lost Planet’s gameplay is how your character, when hit, goes into a script where he stumbles, falls to the ground, and then shakes it off and stands back up—the entire time you wait helplessly. So, as luck would have it, the Spider Akrid just loves using it’s gangly legs to inexorably pound you into oblivion should you be on foot. Then, it releases a ton of those mini-bugs that knock you down upon contact. As if that weren’t enough, it then spins a giant spider web that traps you in close confines with the mini-bugs; and repeat. Add in some terrible hit detection and this boss catapulted my frustration to a whole new level.

Hostage rescue COD

In-flight Hostage Rescue, Call of Duty 4 epilogue, Xbox 360 (“Veteran” on single-player)
Once you complete the game and wait until the credits stop rolling, you’re automatically warped to this entirely unexpected level that doesn’t seem to have any tie-in with the game. Serendipity! Not so fast. You find yourself on a large passenger jet, tasked with eliminating all the terrorists, locating a VIP, and parachuting to safety. Yes, there is a timer, so you’ve got to progress at a fairly brisk pace. It’s frenetic, it’s a blur, and it’s throw-your-controller difficult. If you finish the mission, you are rewarded with an achievement (nicknamed “the mile-high club”). After 40 or so attempts, and a few oh-so-close moments, I never did complete it.

Archfiend toughest video game boss

Archfiend, Ninja Gaiden 2, Xbox 360
First of all, I’m not a fan of games where you think you just beat the final boss, only to be introduced to the real final boss. It's just demoralizing. I played through the entire game, and ended up spending a disproportionate amount of time battling the Archfiend, who I learned to hate. It only made matters worse that I thought this was the final boss. Following several punch-the-couch-out-of-frustration episodes, I finally laid this beast to rest--having to rely upon a bow and arrow didn't help matters. Then, get this, I meet the REAL final boss--what the?! I gave it a few attempts, but ended up having an epiphany--I realized that I wasn’t having fun any longer and retired this game to the archives. The easiest thing to do was just let your character die and go make a sandwich. Never played it again.

Mounted Samurai, Ninja Gaiden, Xbox
Though many gamers heralded Alma as the toughest boss, I found the mounted Samurai in level two to be a major headache (in fact, I couldn't even find a picture of him online
that's how irrelevant he must have been to the gaming community). Maybe it was because I was still learning the controls, but it must have taken me 30 attempts. The various warriors taking pot shots at you definitely increases the frustration factor. When I finally defeated that equestrian bastard, I think I may have done some sort of white-guy dance. I just didn't think Alma was that toughin fact, I beat her on the second attempt.

List of difficult video game bosses

Keep in mind—generally speaking, we now invest more time on each boss than in prior generations. For example, NES boss battles often ended within 60 seconds or less, win or lose. Today, we have protracted confrontations in expanded game environments that can last five minutes or more.

As a result, there’s a greater time investment required so I find myself getting more frustrated when I lose, and thus my list of most difficult and frustrating video game bosses of all time is primarily from games produced within the last ten years.

Come to think of it, I remember being really frustrated with some boss battles playing Fester’s Quest for the NES. Definitely an honorable mention.

Thanks for reviewing my list of the toughest video game bosses of all time!