The Trickiest Retro Video Game Levels

The Ocarina of Time retro video game levels

In the late '80s and early '90s—the heyday of old-school platformers—video games could only aspire to so much. Open-world adventures, realistic physics simulations, or online competition would not arrive for years. Gamers found themselves left looking at 8-bit canvasses that tended to scroll from left to right.

With heavy limitations on the gameplay style, making the game harder often seemed the best way to distinguish the product. The result turned out that we now look back on the time as having produced some of gaming's most difficult titles.

We've put together a list of some retro video game levels from these titles that will likely remain challenging for generations to come.

1. “The Final Fight With Mike” – Mike Tyson's Punch-Out!! (1987, NES)

Mike Tyson as depicted in Mike Tyson's Punch-Out!! on NES
Image Credit: Nintendo.

“Everybody's got a plan until they get punched in the face,” famously said heavyweight champ Mike Tyson, who moonlights as boss of the game in Mike Tyson's Punch-Out!!, the 1987 hit from Nintendo, before later versions replace him with Mr. Dream. Protagonist Little Mac seems comically undersized compared to Tyson in this exaggerated David v. Goliath matchup. Any blows Tyson lands in the first 90 seconds will guarantee a knockout, ratcheting the stakes to crazy levels of tension. The punches arrive nearly instantaneously and with no easy-to-discern pattern. Few casual players will beat the champ.

2. “Turbo Tunnel” – Battletoads (1991, NES)

Battletoads level Turbo Tunnel
Image Credit: Mayasa and Tradewest.

The NES classic Battletoads features a maddeningly difficult level called “Turbo Tunnel” that deserves a viewing on YouTube. The level, which takes place inside the body of a monster, begins easily enough with straightforward beat-em-up action. Then, in a somewhat unwelcome acceleration, the player mounts a hoverbike that reaches ludicrous speeds, with chasms and obstacles incoming. Screw up any one of these nearly impossible-to-predict challenges and get ready to start again from the beginning.

3. “Welcome to the Machine” – Ecco the Dolphin (1992, Sega Genesis)

"Welcome to the Machine" - Ecco the Dolphin (1992, Sega Genesis)
Image Credit: Sega.

Sega Genesis played with themes of environmentalism and the erosion of habitats when it put out Ecco the Dolphin in 1992. While most of the game occurs in serene, natural environments, the “Welcome to the Machine” level places the titular dolphin inside a biomechanical fortress that reeks of oppression and entrapment. The player must fight off monsters with his sonar blasts—or echoes—as the map constantly moves forward, threatening to grind Ecco into fish food between underwater features and the edge of the screen.

4. “Heat Man's Stage” – Mega Man 2 (NES, 1988)

"Heat Man's Stage" - Mega Man 2 (NES, 1988)
Image Credit: Capcom.

Mega Man 2 has more than its fair share of style, with each level layout embodying its boss character. The infamous “Heat Man Stage,” known for its stapler-like enemy, combines intense reds and yellows in a lava-filled gauntlet Mega Man must cross. Blocks disappear without a clear timing pattern, making every moment life-or-death. Luckily, some relief lies in the ease with which one can get the robot enemies to scroll off the side of the screen.

5. “Tubular” – Super Mario World (SNES, 1990)

Super Mario World level Tubular
Image Credit: Nintendo.

Nestled within the Special World of Super Mario World, the “Tubular” stage presents us with the ephemeral balloon power-up, which swells Mario and allows him to drift through the skies. Unfortunately, the ballooned state only lasts a few seconds, forcing players to find additional power-ups, and therein lies the heart of the challenge. To make matters worse, a brigade of Chargin' Chucks fling fireballs at Mario as he makes his way across this groundless level, while Winged Goombas further hazard the airspace.

6. “Dam Level” – Teenage Mutant Ninja Turtles (NES, 1989)

"Dam Level" - Teenage Mutant Ninja Turtles (NES, 1989)
Image Credit: Konami, Ultra Games, and Palcom.

Teenage Mutant Ninja Turtles mostly takes place on the streets of New York or in its sewers, from whence the turtles spring; however, the near-mythically difficult “Dam Level” offers up an underwater challenge full of tension and precision. The turtle must defuse a series of bombs while passing through electric coils and electrified pink seaweed in tight aquatic pathways. Over the years, the stage has gained notoriety among players as one of the most frustrating retro video game levels.

7. “Death Egg Zone” – Sonic the Hedgehog 2 (Sega Genesis, 1992)

"Death Egg Zone" - Sonic the Hedgehog 2 (Sega Genesis, 1992)
Image Credit: Sega.

In Sonic the Hedgehog 2, villain Dr. Robotnik has decked out his space station with jutting spikes and energy beams that Sonic must overcome in the run-up to the crowning challenge of facing the doctor himself. First, players face off against Metal Sonic, a hedgehog doppelgänger that is frankly not that difficult. Then, we have the Robotnik mech: AKA the death egg robot, a baddie armed with a rocket hammer and flamethrowers. The trick: The player has to attack the death egg robot while it stands still, or Sonic dies.

8. “Elevator Action” – Super Castlevania IV (1991, SNES)

"Elevator Action" - Super Castlevania IV (1991, SNES)
Image Credit: Konami.

Players of Super Castlevania IV descend into Dracula's castle, encountering the frustrating “Elevator Action” segment at stage eight. At first glance, the concept seems simple: vampire hunter Simon Belmont only has to move through the seemingly straightforward level, and yet from all directions, adversaries creep, fly, and lunge. Medusa Heads with sine wave flight patterns, handsy wall-affixed skeletons, and those ubiquitous spikes loom everywhere, threatening to send Simon back to square one at every move. Many a Gen X-er lost sleep trying to solve this, one of the toughest retro video game levels.

9. “Rainbow Road” – (1996, N64)

Rainbow Road, Mario Kart 64
Image Credit: Nintendo.

The Mario Kart series reprises the “Rainbow Road” level again and again, adding new hair-raising challenges in each edition. The Mario Kart 64 version continues to stand out, with its nauseating turns without guardrails and psychedelic visuals that can easily distract. The level feels like racing along a neon ribbon in the sky while alternatively hitting and dodging an endless array of power-ups and obstacles.

10. “Area 6” – Star Fox 64 (1997, N64)

Level 6 of Star Fox 64 on N64
Image Credit: Nintendo.

The classic rail shooter Star Fox 64 demands players get through the tricky “Area 6” penultimate level to reach the planet Venom and take on the villainous Andross. Fox McCloud must pilot his Arwing fighter through gauntlets of intricately patterned enemy rounds and use his limited supply of Nova Bombs and energy shields to come out in one piece. Whether to engage or evade certain enemies proves crucial to reaching the final battle with the Gorgon space station.

11. “The Water Temple” – The Legend of Zelda: Ocarina of Time (1998, N64)

The Water Temple in The Legend of Zelda: Ocarina of Time
Image Credit: Nintendo.

The Legend of Zelda: Ocarina of Time, one of the all-time great N64 games, features a challenging dungeon level called “The Water Temple.” Beneath Lake Hylia, gamers must don Link's iron boots to maneuver in this waterlogged and melancholy architectural puzzle. Water levels fluctuate, corridors twist, and those precious keys always feel just a bit too hard to find. “The Song of Time,” played on Link's trusty Ocarina, can raise or lower the water, letting the longsuffering elf reach new heights—or depths—while the Skulltulas stalk our hero as he seeks out the big baddie Morpha.

12. “Alien's Lair” – Contra (1987; Arcade, NES) 

"Alien's Lair" - Contra (1987; Arcade, NES) 
Image Credit: Konami.

The original Contra, one of the most popular games from the NES era, concludes with the level “Alien's Lair,” which feels heavily inspired by Ridley Scott's Alien. The level departs from the game's jungle settings to venture into the bizarre and grotesque, with a fleshy landscape complete with pulsating walls and erratic flying creatures. Power-ups do not abound, and one false move can quickly end things well before reaching the final boss—the beating heart of the alien.

Author: Tim Rinaldi

Bio:

Tim Rinaldi is a journalist who spent his youth inside a video game console, occasionally emerging to read novels and watch films. After earning his degree in Literature from Fordham University, he moved to China over a decade ago to teach English and learn the language, eventually migrating to Taiwan. There, he served as an editor at the nation’s primary English-language daily, Taiwan News, contributing to coverage spanning the arts, business, finance, Chinese politics, and cross-strait relations. Today, Tim is a freelance writer reporting on entertainment, personal finance, and other topics. In his spare time, he tinkers with 3D software like Blender and aspires to craft animated short films.