The difficult game at the moment that everyone is discussing/arguing over/rage quitting is Sekiro: Shadows Die Twice, with beating it being a point of pride and proof of one's gaming prowess. Meanwhile, Sekiro gives you unlimited lives, never forces you to have to start the whole game over again, doesn't require memorizing enemy patterns for entire levels, and never asks you to jump on moving platforms the size of a grain of rice. In other words: It's got nothing on the hardest games that the 1990s had to offer.
A case can definitely be made that the '90s is the toughest overall decade in video game history. The early parts of the decade saw the last gasps of the brutal era that was inspired by a desire to make games as difficult as possible so you'd have to keep pumping quarters into them, followed by the rise of hardcore PC gaming as well as fiendishly difficult 3D platformers and action games. It all conspired to make for an era of gaming that was difficult almost across the board, before the turn of the millennium and a new push to make games more mainstream than ever brought with it hand-holding tutorials, infinite continues, and auto-regenerating health.
Even modern games that aim to bring back '90s-era difficulty often do so with various quality-of-life tweaks that never would've flown 20 years ago. We'll probably never see another era like the '90s in terms of pure video game difficulty, and if you think we're overstating how hard games were back then, this list will surely change your mind (and cause painful flashbacks if you lived through this decade).
25 Aztec (Goldeneye 007)
Based on the movie Moonraker rather than the titular Bond film, the 19th stage of the iconic N64 shooter Goldeneye 007 was the stuff of nightmares even on default 00 Agent difficulty. Even just the basic guard enemies you'd been mowing down up to that point suddenly turned into super-soldiers in the Aztec stage.
Not only are they armed with two of the most powerful weapons in the whole game— the Moonraker Laser and the AR33 Rifle— but they are faster and more accurate than any other stage's basic enemy types. And we haven't even touched on Jaws, who dual wields AR33s!
24 Down The Tubes (Earthworm Jim)
One of the things that a lot of us forget when we reminisce about the greatness of Earthworm Jim is how fiendishly difficult it could be at times. But Down the Tubes— more specifically, the Tube Race portion— was a slimy one, for sure.
You had to steer a submarine through tight tunnels that were just big enough for it, with crashes not only causing you to lose health but also time. And that latter part is important, as the stage's timer seemed to only allow for a near-flawless run in order to make it under the deadline.
23 Cortex Power (Crash Bandicoot)
Speaking of forgetting about difficulty, it wasn't until people picked up the recent N. Sane Trilogy and revisited the original Crash Bandicoot that they remembered— or discovered for the first time— what a tough game it was/is.
It was bad enough that Crash 1 was still old school in that a Game Over could mean having to replay several already-beaten levels, something that was thankfully adjusted in the remake. But the Cortex Power stage encapsulates everything that made that first game challenging (and cheap), and will likely be the quitting point for a lot of people playing the collection when they switch over to the much more forgiving Crash 2 instead.
22 Wave Man Stage (Mega Man 5)
The Mega Man series as a whole presents some of the toughest challenges in video game history, and the NES originals are a primary reason why the term "Nintendo Hard" was coined.
If there is a single stage that demonstrates just how unforgiving the MM games can be— with the relentlessly difficult MM9 and MM10 being disqualified for not coming out in the '90s— it would have to be the Wave Man stage from the fifth core installment. From the steam-spouting pipes to jumping across tiny moving bubbles and, finally, riding on that slippery jet ski, Wave Man's stage requires almost superhuman controller mastery.
21 Elephant Graveyard (The Lion King)
'90s kids who were both gamers and Disney fans got to experience a golden age of those two things coming together, with some excellent platformers based on Disney properties released for various 8- and 16-bit systems. For all the fun that was had reliving our favorite Disney movies and shows in video game form, some of them were heartrendingly difficult.
We'll never know why the team behind the Lion King game decided to make it so hard, but it's honestly one of the toughest overall games of all time. Especially the nightmare fuel that was the Elephant Graveyard stage.
20 The Hammer Falls (StarCraft)
It should go without saying that we'll be getting to some iconic PC FPSs from the decade later in this list, but that's not the only genre that had '90s gamers tempted to kick a hole in their desktops.
StarCraft definitely belongs on any shortlist of the most influential games of all time, and final Terran level "The Hammer Falls" also belongs lists of most challenging missions in a strategy game. Starting with little in the way of base structures is just the first of many disadvantages that must be overcome in this relentless and frustrating skirmish.
19 Tubular (Super Mario World)
A lot of people like to dismiss Mario games as being childishly easy, and a lot of the time, that is true. But when a Super Mario game gets tough, it separates the men from the boys, so to speak.
The toughest stage in any 2D Mario game— yes, even including Lost Levels— Tubular from Super Mario World is a completely floor-less level that needed to be navigated using the unwieldy P-Balloon ability. One hit and you were done for, and the P-Balloons only lasted just long enough to get to the next one.
18 Big Boulder Alley (Frogger: He's Back!)
Whenever a classic game franchise was revived in 3D during the late-'90s, the smart thing to do was to be incredibly skeptical about the results. But not all such examples of that were a disaster, with 1997's Frogger reboot being one of the better ones.
The stiff, jerky movement was meant to replicate the original, but it also ended up making the game that much harder in later levels. Big Boulder Alley is also an area where the third dimension was a detriment, with bouncing boulders that were tough to judge the position of and resulted in a lot of squashed frogs.
17 Welcome To The Machine (Ecco The Dolphin)
The Sega Genesis is home to several games that are so insanely difficult that many gamers have never even gotten past the first level. The beautiful— yet confounding— Ecco the Dolphin is perhaps the most-owned, most-played Genesis game with which few people have seen the second stage.
Tough out Ecco long enough, and you'll get to the real stuff of "Sega Hard" nightmares, Welcome to the Machine. It probably wouldn't be an exaggeration to say that only a few dozen people have ever gotten to this stage and then beaten it without cheats or emulator-specific assistance.
16 Stage 8 (Super Castlevania IV)
Not that the post-Symphony of the Night "Metroidvania" installments were a cake walk, but the classic-style Castlevania games remain some of the toughest side-scrollers ever made. And while each of them have their notorious stages, Super Castlevania IV's eighth level is the toughest thing that Simon Belmont has faced this side of his awful portrayal in Captain N.
In fact, this is one of the rare examples where a Castlevania stage is difficult to the point of feeling unfair, taking the cheap game overs that the series typically uses sparingly and instead throwing them at you every few steps.
15 Rusty Bucket Bay (Banjo-Kazooie)
"I'm Banjo! And I'm going to make you want to break your N64 controller faster than a round of Mario Party!" Rare's 3D platformers for the N64 were legendary and are a big part of why the console was and still is so beloved— but they could also be irritatingly difficult.
If you thought Conker had a potty mouth, wait until you try to take on Rusty Bucket Bay. If there is any stage in Banjo-Kazooie that'll make you want to abandon trying to collect every doodad and thingamajig and just get through the thing, it's this one.
14 C-130 Wreck Site (Syphon Filter 2)
After the first Syphon Filter felt like a fun but shameless rip-off of Metal Gear Solid, its sequel developed a more distinct vibe and story and really helped the franchise come into its own.
That said, Syphon Filter 2 could get extremely difficult at times, most notably in the level that begins after the crash of a C-130 aircraft. Among the biggest challenge is the army of snipers that seem incapable of missing, and you basically have to spend the level in an almost-constant dodge roll to stay alive. The level looks really cool, though!
13 Mars Needs Cheerleaders (Zombies Ate My Neighbors)
One of the 16-bit era's great sleeper hits, Zombies Ate My Neighbors is comes packed with nearly 50 stages of zombie-shooting and neighbor-rescuing action. Obviously, things are pretty crazy difficulty-wise by the end, but it's the game's 12th level that is its most infuriating.
The zombies in Mars Needs Cheerleaders seem to know how to stay a really annoying distance from you in order to render your best weapons useless against them. The one saving grace is that the punishing spaceship boss is possible to avoid fighting, but when you aren't that lucky, well...
12 Animal Antics (Donkey Kong Country 2)
Back in the SNES days, Rare was one of the only "outside developers" that Nintendo trusted enough to make platform games using its iconic properties. The resulting Donkey Kong Country trilogy certainly didn't have them regretting that decision, literally helping to turn the tide in the 16-bit war and giving Donkey Kong himself a new look that he maintains to this day.
The DKC games were also crazy hard at times, none more difficult than the second game and, in particular, the notorious Animal Antics stage. You thought you hated the swimming stages? The "flying" ones are way worse.
11 Lud's Gate (Tomb Raider III)
Tomb Raider III sometimes get lumped in with the series' decline in its later PlayStation years, but that's not fair, as its a solid sequel that is almost as good as the celebrated second installment. If people have sour memories of Lara's third outing, it's likely due to its high difficulty.
The early portions of the Lud's Gate stage are deceptively chill. But then you're thrown into a dimly-lit underwater maze gauntlet that would've been tricky enough without forcing you to navigate it in a clunky submarine thing. Oh, and TRIII dropped the ability to let you save anywhere, so good luck returning to far-back checkpoints when you fail.
10 Stage 5 (Gunstar Heroes)
When some of the key people behind the Contra series left Konami to start their own independent studio, they immediately proved that Treasure was a force to be reckoned with when its very first release was the action masterpiece Gunstar Heroes.
Feeling like a game full of crazy ideas that the team clearly had for Contra but probably weren't allowed to do, Gunstar is also often much more difficult than any Contra game— particularly its fifth stage, which isn't afraid to go on for way too long but still not let up for even a second.
9 The Elder God Shrine (Quake)
Unless you were around for the peak years of id, Epic, and 3D Realms in the '90s, you have no idea what a "difficult first-person shooter" really is. Quake was the first FPS that id created that was truly 3D, and you better believe that they made full use of having action that could literally come at you from any direction.
It would be interesting to take some tough-talking, Prestige-ranked modern Call of Duty player, drop them into the Elder God Shrine stage of Quake, and watch the game have them humbled within mere minutes.
8 Rainbow Road (Super Mario Kart)
If you get a little shudder when you hear the words "Rainbow Road," it's likely because you are an OG Mario Kart player who remembers the original incarnation of the token final race. The original SNES Rainbow Road had zero walls or boundaries of any kind— so good luck if you had been relying on bumping things in order to stay on the track.
And you'd better make sure you stay in a comfortable first place the whole time as well, as anyone who bumps you as they pass— and everyone will— almost always sends you sailing off the narrow track.
7 Pencil Pentathlon (Rayman)
As the hype for Beyond Good & Evil 2 (very slowly) builds, it's the perfect time to look back at the game that put Michel Ancel on the map— the innovative, gorgeous, and unforgivably difficult Rayman.
The entire Band Land world is brutal and almost any stage from that could've made this list, but Pencil Pentathlon is the best (worst?) example of what made that world— and the game itself— so frustrating. This is the point in most gamers' relationship with Rayman that the charm of its good looks starts to wear off and its quirks become much less tolerable.
6 Water Temple (The Legend Of Zelda: Ocarina Of Time)
No video game is perfect, but some come really close (at least for their time)... The Legend of Zelda: Ocarina of Time is definitely a candidate for a game that flirts with perfection. Unfortunately, the two-hit combo of the Water Temple and the fight with Dark Link are enough to keep this masterpiece from being truly flawless.
The Water Temple's puzzles are an exercise in old-school tedium and trial-and-error, and the Dark Link battle, while one of the coolest moments in gaming history just before the fight begins, is a beast until you figure it out. Which typically takes approximately 255 retries.
5 Xen (Half-Life)
When a game isn't specifically built around precision jumping, trying to shoehorn platforming into it ends up feeling awkward and frustrating— but almost every game in the '90s thought this was a requirement. And few levels are more notorious examples of this than Half-Life's Xen area.
As if first-person jumping in a game that isn't Metroid Prime or Jumping Flash isn't bad enough, Xen takes place in low gravity— a gimmick which never fails to be terrible. Cap this off with a horrible final boss fight, and Xen is a cheaply difficult final stage in an otherwise perfectly-balanced game.
4 Carnival Night Zone, Act 2 (Sonic The Hedgehog 3)
Many of you reading this clenched your fists as soon as you saw that screenshot of Sonic standing on what has been nicknamed the "barrel of doom." The second act of Carnival Night Zone is difficult enough with its very tight time limit, ending with a Robotnik battle that seemed particularly designed to take as long as possible.
But what really makes this stage legendary is that you encounter a barrel that requires you to do something that makes little contextual sense in order to get past it. Ah, the obtuseness of '90s gaming, how we haven't missed thee!
3 Stage 4 (R-Type III: The Third Lightning)
It was hard not to have half of this list be stages from shmups, as it is a genre that is notorious for its difficulty and for weeding out casual players literally within seconds of pressing start.
The fourth stage of classic R-Type III serves as a pretty good representative for how absurdly difficult shmups can be. Not only is much of the stage on a diagonal incline— one of the trickiest angles to play a shmup in— but the second half of the stage involves you replaying the first half in reverse, which is fun since you can't turn around or shoot behind your ship.
2 The President's Run (Driver: You Are The Wheelman)
Driver has the distinction of being one of the only video games in history with a tutorial that people literally struggled to beat. It's probably more accurate to describe the infamous parking garage segment as a test to determine who was (and wasn't) going to be able to handle the rest of the game.
It should go without saying that a level with a challenging tutorial level would have an absolute beast of a final stage. The President's Run mission starts off relentless and never lets up even a little bit, requiring an almost more-than-perfect performance against completely unfair odds from start to finish.
1 Clinger-Winger (Battletoads)
Everyone immediately thinks of the speederbike portion in the third stage of Battletoads when discussing how difficult that game is. And it's true that a lot of people quit and swear off the game forever after that point.
But there is still a whole bunch more game after that, and not surprisingly, it gets even more difficult. You see people brag about how easy the speederbike part was/is for them, but ask those same show-offs how many times they've finished nigh-impossible final stage Clinger Winger. If they tell you give you any number besides zero, be extremely skeptical.