Difficult choice.
I played Railroad Tycoon a lot, it was a very addictive building sim. I still know you could place 32 signals max to optimize the network, as well as max number of trains that could be running. It was so cool to see the cities grow over time after you connect them to the network, the landscape slowly changing from pastoral little villages to mega cities on the busy junctions.
Priority missions were fun to make some extra cash, get an express to deliver something asap by rerouting and stopping other traffic in the way. Then you had rivals you could start delivery wars with to win the rights over stations to expand your territory. Basically flooding those stations with products while making sure to always have trains standing by to hover up all cargo.
The best of all was making things run like clockwork, upgrading goods from mine/farm to bulk processing to factories to sell in cities with the highest demand. Yet mines would deplete over time so the work was never done. While in the late stage cities were big enough to shift money making to passengers and mail express trains.
This year also birthed Stunts
A game I played for many years just like Railroad Tycoon. The track editor was amazing and I made tracks with ridiculous jumps abusing the max speed glitch in one of the cars.
The Secret of Monkey Island totally blew me away at the time. I first played it at my friend's house on Amiga 500, then got a copy for PC. From text based entry to point and click, Monkey island made the transition flawlessly. It's such an influential game it's still remade and now already has a second appearance / season on Sea of Thieves. I played the remake while switching back and forth between the old and new style, I wish all remakes had that option :) Plus it was the first game that gave me ear worms, the music is still stuck in my head :)
My vote goes to Monkey Island.
