The premise is simple: while studying for a test one night, Bart falls asleep and begins to dream. Within the dream, Bart has to evade enemies and collect the missing pages of his homework, so that when he wakes up he can pass the test and get a good grade.
The game drops players into the Hub World "Windy World", where Bart must evade various enemies and collect power-ups while searching for the pages of his homework blowing down the street. Bart's health is represented by a bar of Zs along the top of the screen; by blowing a bubblegum bubble into Zs he comes across, he can float them up to the top of the screen and catch them in the Z bar. By jumping into the homework pages when he finds one, Bart enters different worlds to retrieve his homework. The levels are:
- The Itchy & Scratchy Show: The Simpsons' house has been taken over by Itchy & Scratchy and other enemies, who fight Bart with slapstick hijinks. Visited twice.
- The Temple of Maggie: A Raiders of the Lost Parody world where Bart must make his way through the trap-filled Temple of Maggie. Visited once with two levels, each with a page.
- Bartman: A flying level where Bart as Bartman patrols the skies above Springfield fighting enemies with his trusty slingshot. Visited once.
- Bartzilla: Bart as a Notzilla rampages through the city before being shrunken down to climb a skyscraper and face King Homer and Momthra. Visited once with two levels, each with a page.
- Bart's Bloodstream: A Womb Level where a shrunken Bart fights off military germs in a bloodstream. Visited once.
The game is notable for its steep difficulty curve, more due to Fake Difficulty than actual difficulty.
This game provides examples of:
- Adaptational Villainy: Considering this is from the first seasons of The Simpsons, it makes sense that in the Bartman levels you'd fight Sherri and Terry, who liked to annoy Bart, or Smithers, who was only known for being Burns' loyal toady. But even back then there was no reason for Bart to fight with Barney Gumble.
- Anti-Frustration Features:
- Ironic given the game's brutal difficulty otherwise, the Temple of Maggie and Bartzilla stages have this. The stages are divided into two parts, each with a page to get, but you play through the entire thing on your first trip. If you complete the first part but fail in the second, you still get credit for the page from the first part, and when you revisit the stage later you can continue from the second part.
- The Itchy & Scratchy levels both have spots where you can freely farm extra lives, the bouncing eyeballs from the family portraits and the light bulbs thrown from the lamps. The only trick is timing your attacks to hit them, which isn't too difficult.
- The shrink ray in the Bartzilla stage won't be destroyed by the explosion from a nuclear plant's destruction, which otherwise destroys all enemies. Since there's no way to stop from destroying the plants when they happen to appear in your way, this averts you being forced to destroy the shrink ray for lack of control.
- Cursed with Awesome: The suit prevents Bart from attacking and slows his movement rate, but also stops him from taking damage from anything but Jimbo and his gang. It's worth it if you're in a jam.
- Damage-Sponge Boss: The furnace at the end of the second Itchy & Scratchy level has a fairly simple pattern you'll get used to quickly, but it takes an ungodly amount of damage to kill.
- Damn You, Muscle Memory!: The Genesis version puts the Windy World jump button on A. This is extremely rare among Genesis games that have different actions mapped to A, B, and C (most games put jump on C).
- Difficult, but Awesome: Jumping over a basketball in Windy World spawns a skateboard for Bart to ride, but as soon as he hits an enemy or rides over a crack in the ground, he falls off. The clunky controls make it difficult to jump over the bouncing basketball, and the increased movement speed coupled with the random spawns of enemies means it's difficult to stay on the skateboard for any substantial amount of time. However, if you can manage to stay on, Bart's Z bar will steadily increase and even expand to the sides to make room. Given how difficult it can be to acquire Zs randomly, mastering the skateboard is a huge advantage for surviving Windy World.
- Disappointed in You: Earning anything below a C has Marge, Homer, and Lisa glare at Bart with obvious disappointment. Bart himself looks at the floor in shame.
- Double Take: Should you receive the Good Ending, Lisa will look at the grade on the fridge, back at her brother, and back at the fridge again, unable to believe what she was seeing.
- Everything Trying to Kill You: Mailboxes, Jebediah heads, saxophones, Jimbo and his gang, Otto driving the school bus, the three-eyed fish... about the only friendly things in Windy World are the old woman and Skinner. This applies for the rest of the game too, with the only friend in the five stages being Apu in the Bartman stage, as he'll toss out a squishie health refill... as well as leave behind fragments of his flying carpet to attack you.
- Expressive Health Bar: Bart's face is present in his health bar and it goes from fine and confident to skeleton upon death. The color also starts to drain from his face as he nears death, going from a darker yellow, to green, to grey, and then skeleton.
- Fake Difficulty: Pretty much the design philosophy of the entire game. Guide Dang It!, Luck-Based Mission, and Trial-and-Error Gameplay are in full force and combined with clunky controls and hitboxes, and they make the game much more challenging than it would be otherwise.
- Windy World is full of enemies who are difficult to time jumps over or can only be killed by specific power-ups. Because pages spawn at random, you can spend real-time minutes wandering the street looking for a level entrance as enemies whittle down your HP and power-ups. For that matter, enemies, power-ups, and Zs to refill your life bar are also randomly generated and they become more scarce as you collect homework pages.
- In several stages, enemies can attack you from off-screen, and in the Bartman stage they can do it vertically as well as horizontally. The second Bartzilla stage may have enemies chain their attacks if you're unlucky, allowing them to knock you off the screen and kill you. The Itchy and Scratch stage not only has enemies that can attack from off-screen, but they'll deal a One-Hit KO.
- In the bloodstream stage, Bart is a One-Hit-Point Wonder, and a single hit from a grenade (which are hard to see) ends the level.
- The Itchy and Scratchy world is full of enemies who can kill you in one hit, and if you get hit by anything you lose your current weapon and go back to the mallet, which has a small melee hitbox and a slow attack speed.
- Forced Transformation: Getting hit by Fairy Lisa's magic dust turns Bart into a frog. If you hit the flying sax while trapped by Jimbo's gang, she will appear and turn them into rats.
- Foreshadowing: The latter half of the Bartman stage pits you against Smithers in a blimp twice, and sandwiched between these fights is a flight over the nuclear power plant with clouds of radiation in the sky. Between the location and the presence of Smithers, it isn't hard to guess that Mr. Burns will be the stage's Final Boss.
- Giant Space Flea from Nowhere: The final boss of the second Itchy and Scratchy level is... a furnace. It's ostensibly a reference to Home Alone, but it still comes out of nowhere.
- Guide Dang It!: The game opens with a title screen, Bart falling asleep, and then you're dumped into Windy World. If you don't know what to do from there, too bad.
- Certain enemies in Windy World can only be killed by certain power-ups, such as the TV only being vulnerable to otherwise useless watermelon seeds.
- In order to enter the actual levels of the game, you need to not just walk over the homework pages but jump into them. Even if a player takes an interest in the pages blowing down the street, it's not unlikely they'll be unable to figure out what to do with it.
- Each level has its own gameplay style and control scheme entirely different from Windy World and each other. The Bartzilla doubles down on this, with the stage divided into two parts that are each totally different. The Itchy and Scratchy stage and the Bartman stage have some similarities, in that they're side-scrolling action games and Bartz has extra lives and a health meter, but they otherwise play differently too.
- Scrolling the screen ahead left or right seems fairly useless, but it's critical to survival in the Temple of Maggie because the statues in the background shoot their pacifiers depending on the screen position, so players can trick them into firing when they're nowhere near the line of fire.
- Hub World: Windy World, where Bart has to find and enter his homework pages to get them back. Unusually for the trope, you'll spend far more time in Windy World than in the actual levels.
- Luck-Based Mission: Because Windy World is randomly generated, it's possible to find yourself assailed by enemies with no Zs in sight and thus you'll die quickly before ever seeing a page. Or you could run into a string of Zs in perfect position to get collected, or have a page blow on-screen the second you spawn.
- Multiple Endings: Depending on the grade Bart gets on his paper:
- F or D: The Bad Ending. Bart is disappointed and the rest of his family are all displeased with him.
- C: Bart seems pleased with his grade, as does Homer. Marge is still unimpressed and Lisa continues to mock him.
- B: Marge is satisfied with Bart's grade, but Lisa continues to mock him for it.
- A: The Good Ending. Lisa, finally, is aghast that Bart managed to get an "A", meaning that all of the Simpsons (except for Maggie, who of course reacts the same in every ending) are impressed with him.
- Obstructive Foreground: The trees in the foreground of Windy World block your view of anything behind them, whether it be enemies, manholes, or the very pages you're looking for.
- One-Hit Kill:
- The Itchy and Scratchy world is full of one-hit deaths. All fire based attacks are instantly fatal to Bart, with the little boy crumbling to ashes.
- In Bart's bloodstream, getting hit with a grenade from a virus instantly sends you back to Windy World.
- Player Nudge: If the player gets caught by Jimbo and his gang, saxophones start continuously flying past you. It's a hint to hit one of them and summon Lisa to turn them into rats.
- Projectile Kiss: An old lady known only as "Grandma" wanders the streets in Windy World and blows a kiss to Bart. If it connects with the young Simpson, he will be unharmed but will lose points. If Bart had been transformed into a frog, the kiss will return him to normal.
- Reduced to Dust: Bart immediately disintegrates if the young boy is hit by a fire-based attack.
- Schmuck Bait: Early in the Temple of Maggie, bird eggs will be tossed onto a pillar in plain view. Collecting them earns Bart a 1-up, but the reason it's Schmuck Bait is that its quite difficult to make it to the egg before a bird drops down to grab it, and if Bart is caught by the bird instead, he dies.
- So Proud of You: Achieving higher grades pleases Homer and Marge. Getting an A grade has Lisa stare at Bart with utter disbelief.
- This Is Gonna Suck: Getting below a C has Bart utter "Uh oh...", realizing his family is about to be very unhappy with him.
- Trial-and-Error Gameplay: A lot.
- As mentioned, the game never has any sort of tutorial or makes any effort to explain the gameplay and your objectives. If you don't have the manual or an online guide to explain things to you, you'll figure out how to play by pressing random buttons and remembering what does what.
- The Temple of Maggie consists of stone columns where stepping on one makes another rise, and it's always the same ones. If a column falls too low, jumping on it kills you. Eventually you'll get to points where the entire line of columns ahead are at their lowest point, so it's time to randomly jump on other columns and see which one makes the path open up.
- In the bloodstream stage, you disable the force field protecting the page by blowing up viruses who aren't wearing helmets, which causes Smilin' Joe Fission to appear. The game never makes this clear to you; while you'll probably figure out that touching Smilin' Joe causes the force field to weaken, it isn't clear that he appears when you kill a specific type of enemies.
- Two Roads Before You: Jumping on a page presents you with two choices of doors.
- Unintentionally Unwinnable: Only in the levels, fortunately; dying in them just takes you back to Windy World and you can try again later. Still...
- In the Bartzilla stage, the stage ends when the military shrink ray comes out and shrinks you. If you accidentally kill it (which is very possible since the stage trains you to shoot anything that moves), it'll never respawn and the stage will continue forever until Bart dies. In the second part of the level, you need to electrocute King Homer to win, but each time you use Bart's electrical shock, its duration lowers; eventually it'll last such a short time that it's almost impossible to get Homer with it.
- It's possible to box yourself in on a pillar in the Temple of Maggie stages where any move will end the level. But given that the pillars are connected in no particular pattern, you either have to be very unlucky to have this happen, or be trying to make it happen.
- Unique Items: There's exactly one Sleeping Bart item in the whole game, in the Bartman stage. Its only use is giving you one Z in windy world.
- Violation of Common Sense:
- Lisa will turn Bart into a frog if she gets him with her spell, and killing a flying saxophone always causes Lisa to appear shortly after. But if you get caught by Jimbo and his gang, the only way out is to kill a saxophone and call in Lisa, who inexplicably uses her magic on them instead of you this time.
- Despite it being the point of the entire game, collecting all eight pages has no impact on the ending and Bart's final grade — his grade is based on the player's score, not how many pages they collected. This also means if you spend long enough in Windy World fighting enemies, you can get a high grade without collecting any pages at all.
- A Winner Is You: The ending is the same no matter how many pages you collect; the only thing that changes is the grade on the paper Bart holds up, and if it's high enough the family will smile at him as they look at it, when otherwise they'll scowl.
