Pirate Games on Windows 98/98, on a school PC around 1999 and 2000.
This is a subreddit for finding the name of a game that you can't remember. Read the rules, post your description, and hopefully someone will be able to identify it. Be sure to help out if you think you may have an answer to someone else's post!
In hindsight, this mission from Peace Walker makes a lot more sense...
The subreddit dedicated to Wendigoon and his YouTube channel. Posts range from discussing video ideas to dadposting, among a giant list of other topics.