5 Brutally Hard 2000s Games Nobody Could Beat As A Kid

Published Sep 26, 2026, 10:00 AM EDT

Jared is a writer, editor, and Communications Studies graduate who loves popular nerd culture (almost anything to do with Marvel, DC, Star Wars, or The Lord of the Rings) and the interactive storytelling medium. Jared's first console was the PS1, wherein he fell for Spider-Man, Spyro the Dragon, and Crash Bandicoot.

Video game difficulty will endlessly be a brilliant and intriguing conversation because it’s completely subjective, regardless of how hard a majority of players believe a game is, what difficulty settings players select, how overtuned a game’s tougher difficulty options can be, or how young you were when you first tried and failed to beat a game that you might be able to finish with laughable ease today. Assuming you were a kid in the 2000s, there are plenty of brutally difficult games that probably stumped you.

As an adult, perhaps you’ve mustered the courage to play a game that you couldn’t beat as a kid and found that it isn’t nearly as difficult today as it was when you were younger. That said, some games may have turned out to be tough to beat even when you finally possessed a fully developed prefrontal cortex. Either way, the 2000s were generational for video games. Hopefully, if any of these games bested you as a child, you’ll feel seen and validated in your defeat. And if none of them bested you when you were younger, then maybe you’d ironically find them harder to beat when you’re older.

5 The Legend Of Zelda: Majora’s Mask

The Legend of Zelda games aren’t necessarily known as being the hardest around, but they certainly lend themselves to a particular degree of difficulty regarding how little they hold players’ hands, and it’s no wonder if you weren’t able to beat The Legend of Zelda: Majora’s Mask as a kid due to a frustrating dungeon or puzzle, let alone the perceived pressure of the game’s three-day cycle.

Indeed, The Legend of Zelda: Majora’s Mask may have been one of the first games you played as a child where you got lost and were unsure of where to go or what to do, and playing it with a sibling or having unprecedented patience might’ve been the difference between beating it right then and there and shelving it until adulthood. Merely grasping the concept of the three-day cycle and reliving the same three days might’ve been tough, and that, bundled with The Legend of Zelda’s commonly cryptic design philosophies, made The Legend of Zelda: Majora’s Mask a uniquely stressful game as a kid.

Other 2000s-era Legend of Zelda games were no walk in the park as a kid, either. An official Legend of Zelda: Ocarina of Time remake is launching this November, and anyone who played the original as a kid will likely have PTSD from The Legend of Zelda: Ocarina of Time’s Water Temple as an adult.

4 Spider-Man (2000)

Depending on how old you were when it was released, Neversoft’s iconic Spider-Man might’ve been tremendously difficult, with many levels and encounters being tough to understand. Fans may remember being mildly perplexed by the first level alone, where Spider-Man rescues hostages from the black-clad Jade Syndicate and must figure out what to do with a huge bomb before it detonates.

Navigating enormous, labyrinthine sewers in pursuit of Venom probably proved fairly hard for children. However, if any level might’ve legitimately frightened you and discouraged you from trying to beat the game, it was likely the last one, where players flee from Spider-Man’s Monster-Ock. The hairs on the back of your neck would stand on end as this bone-chilling pursuer is never more than a few inches away from Spider-Man, and the corridors that players must web-swing and web-zip through are torturously narrow, ensuring that every movement players make needs to be calculated.

3 Jak 2

All three of the original Naughty Dog Jak and Daxter games are fairly tough and are increasingly hard, but anyone who wasn’t able or willing to beat Jak 2 would likely agree that the difficulty spike between Jak and Daxter: The Precursor Legacy and Jak 2 was sudden and steep. Jak 2 is arguably a brutally difficult game regardless of whether you’re a kid or an adult, as there are countless missions that players might dread having to revisit on a fresh playthrough later in life, such as taking down five Hellcat Cruisers or fleeing from the Water Slums with the Krimzon Guard on your tail.

Jak 2’s inherent difficulty is appropriate when you assess it narratively, since it’s intended to be a much different experience devoid of all the vibrancy and wonder of Jak and Daxter: The Precursor Legacy. Still, to this day, a lot of what’s aggravating about Jak 2 can boil down to its lack of checkpoints, making many missions a war of attrition that a kid might not have the bandwidth needed to conquer them.

2 Star Wars: Knights Of The Old Republic

If you were a Star Wars fan as a kid but had never played an RPG before, it’s possible that BioWare’s Star Wars: Knights of the Old Republic was your first. There’s an argument to be made that the game is never as hard as it is on the game’s first planet, Star Wars: Knights of the Old Republic’s Taris, and that it actually affords players every resource available to make the game absurdly easy once they train to become a Jedi on Dantooine and trade their vibroblade for a lightsaber.

That said, Taris hurls a lot of tough encounters at players in the first five-or-so hours of Star Wars: Knights of the Old Republic, particularly when fending off pesky rakghouls in Taris’ Undercity. Plus, the intended way to slay Star Wars: Knights of the Old Republic’s rancor, by planting a bait of synthesized odor and a frag grenade in a nearby corpse pile, might have understandably gone over your head as a kid.

With the Star Wars: Knights of the Old Republic remake seemingly dangling on a thinly frayed string, it’ll be interesting to see how hard it is in comparison to the original if it ever manages to see the light of day. If it’s a faithful remake, players should be able to wield the knowledge they have now about Star Wars: Knights of the Old Republic that they didn’t have when they first played it, and earn redemption for their younger selves by beating the remake with relative ease.

1 The Simpsons: Hit & Run

The Simpsons: Hit & Run is a 2000s-era sandbox-style action-adventure game that many kids might not have beaten, despite being able to skip virtually every mission. Considered Grand Theft Auto for children, The Simpsons: Hit & Run is no joke when it comes to difficulty.

It’s the kind of game that has apparently left such a stain on players’ childhoods that they don’t even want to try to beat it later on in life, believing that the satisfaction of enduring such hardship again, regardless of how easy it could be as an adult, wouldn’t be worth the trouble. Its legacy precedes it, with The Simpsons: Hit & Run being many players’ favorite PS2-era game.

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