Windows 98/2k/XP
This 20-level game puts you in the drivers seat of an SUV, with a time limit to find the handicap space. Can you do it without running over people? How about not hitting other cars? It's harder than it sounds...
It even has a multiplayer mode, with split screen action (the only multiplayer game I've ever made actually). Give it a try for some old school fun.
A quick aside...this game was the one that got really popular back in the day and helped me to get better known in the GM community...shortly thereafter the GM Community was founded by a group of us but was ultimately taken down. SUV 2 bombed as well, and lessons were learned the tough way...
NOTE: There is a font in the directory of which you install the game. Put the JAEC font in your FONTS folder.