SimCopter was and still is one of my all-time favorite video games. I remember playing SimCopter quite a lot on our Windows 98 HP Pavilion as a kid; mainly flying around, sometimes completing a mission or two, but always having fun.
This game was far from the best in terms of graphics or programming integrity, but it made up for it in charm. The antics that you cause due to said lack of programming integrity also made for a lot of unintentional fun. The soundtrack (and spoof radio commercials) was great, too...
Here’s an amusing and informative review done by someone else, that also shows gameplay (and the infamous “Easter Egg”):
(I still wish I could have been a helicopter pilot some days...)