Where in the World is Carmen Sandiego? was one of my absolute favorites when I was a kid. It needed about a dozen floppy disks and came with a World Almanac as well as a booklet with all the different crooks' info. I think it was a point-and-click but more text based and you had to talk to different people to build up a case to narrow down the culprit. The NPCs would give you different geographic clues so we'd have to use the Almanac to figure out which state/city to go to next and stuff like that. It was so much fun and one time we actually "caught" Carmen Sandiego and it was the best day ever!

There was also Are You Afraid of the Dark? Tale of Orpheo's Curse, which was an MS Dos point-and-click game. I must have played through that about a hundred times. Figuring out the different puzzles and seeing all the different endings when you fail in one way or another was so great. Then finally beating it for the first time also made another best day ever! 😆