Not even close to a contest, it was the Infiltrator for the NES. When I was a kid we didn't get many games, and my mom picked this out of the budget section at a store. It was in it for good reason.
Infiltrator has two types of gameplay. A kind of sub-Metal Gear spying and, um, infiltration game from a topdown view which is a lot of fun. You'd wear disguises, show enemy spies your papers, use gas bombs to knock them out and hunt around for secret gear and mission objectives. And a helicopter segment to get between those spying sections. It was the helicopter sections that I wasted way too much of a summer trying to get by.
The problem was that despite carefully reading the manual and seemingly being able to pilot Johnny "Jimbo Baby" McGibbits' Gizmo DHX-3 to the bases, I would literally crash every time I tried to land it. Landing the plane in Top Gun had nothing on this. Any little fiddly correction or speed issue or bit of damage sustained in the flight there would cause a crash. But I had tried it so much I thought I'd have to get it at least once. Nope.
At one point in a department store I found the Worlds of Power novelization of the game. It promised secret tips so I opened it and read that section. The only question was how to land the plane, and the book sarcastically repeated the advice from the instruction manual. I tossed the stupid book down in disgust.
In retrospect and reading faqs 20 years later I realized I probably hadn't been focusing enough on getting a perfect run before the landing, as even if you do everything right if some systems are damaged, and they are easily damaged, you'll crash anyway. The manual tells you that damage can cause a crash but I guess I didn't expect it to be that unforgiving.
I did manage to play all three of the fun infiltration levels, because the game has a password system with simple four letter codes that are hinted at in the manual and easy to guess. One was "Bomb," I remember.