?90s? iMac or Windows 95 Pirate Trivia

[Williambrutal]

I was very young, not very clear memory. Game was probably shareware. Game started with a text box and possibly a 2d pirate or monkey head asking pirate trivia questions, but I was always under the assumption there was more to the game because I never even got to a start screen. Felt like you had to answer questions to even start the game? Unfortunately never answered enough correctly to get a score or advance. We had one of the first all-in-one imacs and a windows PC that was probably running windows 95. I think I found it around the same time as MegaSimpsonHomer, another shareware game. I thought the name might have been something "Monkey" or "Pirate" but searches always just turn up curse of monkey island or treasure island.

[MrFlibble]

Maybe look in this list:
https://www.mobygames.com/group/5990/th ... sort:date/

[Swiftcutter]

Redhook's Revenge?