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 homeworld 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.
- 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.
The game is notable for its steep difficulty curve, more due to Fake Difficulty than actual difficulty.
This game provides examples of:
- 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 and collect its page, then fail the second part, when you re-enter the stage from another page you can continue from the second part of the stage, and will still get credit for the first page if you game over.
- 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.
- 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.
- Fake Difficulty: In so many ways. The amount of Guide Dang It!, Luck-Based Mission, and Trial-and-Error Gameplay, combined with clunky controls and hitboxes, make the game far more challenging than it ought to be.
- 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.
- 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. 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.
- 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. Further complicating it is that to enter the pages you need to actually jump into them, not just walk over them, so 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. Also, each level has its own gameplay style and control scheme entirely different from Windy World and each other.
- 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.
- 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.
- Trial-and-Error Gameplay: 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.
- Two Roads Before You: Jumping on a page presents you with two choices of doors.
- Unwinnable by Mistake: 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.
- 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.
- 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. Even if you collect all eight pages, the ending is the same, and getting all eight doesn't even guarantee Bart getting an A — his grade is based on the player's final score, not how many pages they collected.