Guybrush Threepwood from The Secret of Monkey Island (PC, October, 1990), produced by LucasArts of San Francisco, California.
The Monkey Island series remain my favourite point-and-click adventure franchise of all time, though it’s not like there’s much competition in that genre these days. I always particularly admired the amount of in-jokes and subtle visual gags the artists managed to cram into every scene and background. Much harder to do in the 3D era.
Suggested by an anonymous commentator.