The Secret Island of Dr. Quandary

The Secret Island of Dr. Quandary is an Edutainment Game produced in 1993 by MECC, the same brains behind Oregon Trail, Odell Down Under, and the Number Munchers series.

The player character attends a carnival, plays a shooting game hosted by the "Quintessential Quizmaster" Dr. Quandary, and wins a doll "Lifelike Action Figure". But upon claiming their prize, the player's soul is transferred into the doll, which is whisked away to Dr. Quandary's private island. The only way to escape is to solve Dr. Quandary's quandaries and find the ingredients for his "Fixer Elixer"!

... did I mention the whole thing looks like it belongs in the Uncanny Valley?

The Secret Island of Dr. Quandary contains examples of:

 * Deadpan Snarker: The player character has some hilarious comments.
 * Easy Mode Mockery: Once you win the game as B. Ginner, Dr. Quandary challenges you to come back and try again as O. D. Nary or D. Feecult, and even draws attention to the doll's Punny Name.
 * Elmer Fudd Syndrome: The Tax Cowwector.
 * Everythings Better With Monkeys: William Apespeare
 * Evil Laugh: Dr. Quandary cracks two: once when you choose your Lifelike Action Figure after Troggle Shoot, and once in his letter to the player (in writing).
 * Game of Nim: Disc Appear, played with a Beach Dudette and her collection of (rightfully) unwanted compact discs. The loser apparently has to listen to them.
 * Genre Shift: Target-hitting minigames abound, as well as the Acid Test, which is basically a Bullet Hell.
 * Getting Crap Past the Radar: At the carnival, clicking the ferris wheel cars, the ticket booth, the crowd, and the fortune-teller's sign will get you comments. One of the comments from the ferris wheel is "Harder! HARDER!", with the car shaking appropriately.
 * The doll O.D. Nary doesn't seem to be wearing pants.
 * Guide Dang It: The objectives of Tad-Pult are not indicated, nor is the correct post for the Tire Tower puzzle. Fortunately, there is a Help! option in the menu that will tell you these things.
 * Tax Factor can be a case of "Math Class Dang It", as it requires a head for numbers and has been known to stop adult players in their tracks, even on the easier difficulties.
 * Harder Than Hard: "I was certain O. D. Nary would be too much for you... Play as D. Feecult! You'll never make it off the island alive!" Thanks to Tax Factor, he's probably right.
 * Hitbox Dissonance: Makes all the target-hitting mini-games and Acid Test really annoying.
 * Incredibly Lame Pun / Hurricane of Puns
 * Insistent Terminology: Used and then subverted. Dr. Quandary initially insists on calling the dolls "Lifelike Action Figures". Once you're on the island, he makes fun of you being stuck inside the DOLL.
 * Interface Screw: Tunnel Vision, Acid Test.
 * Jerkass: Dr. Quandary. What kind of jerk does that to a kid, and then writes them a letter mocking them about it?
 * Large Ham: The only explanation for Quandary writing an Evil Laugh into his letter for the player character.
 * Medium Awareness: The player character suggests using the Num Lock key (of the computer) to open the Num Lock holding Sir Pillory. Pillory replies that this isn't that kind of program.
 * Mythology Gag: Troggle Shoot at the beginning of the game.
 * Parental Bonus: It seems incredibly unlikely that many of the references would have been understood by the target audience.
 * Punny Name: Choosing a Lifelike Action Figure to play as sets the difficulty for the rest of the game. The names of the dolls reflect this: B. Ginner, O. D. Nary, and D. Feecult.
 * Puzzle Game
 * Rhymes On a Dime: William Apespeare.
 * Robe and Wizard Hat: Subverted. Dr. Quandary wears a purple robe and a matching top hat.
 * Shout Out: To the likes of William Shakespeare, Louis Armstrong, and... Sir Edmund Hillary?
 * "Go ahead. Make my door."
 * Simon Says Mini Game: Ape the Ape, of course! "Watch what I do, then you do it, too."
 * Solve the Soup Cans
 * Towers of Hanoi: The Tire Tower puzzle in a junkyard. The completed tower enables the doll to reach a can of motor oil for the Fixer Elixer.
 * Transformation Trauma: The player character's initial reaction to waking up in the doll.