My worst and best flight involved a check ride before I took delivery of a new R22 for delivery to Northern Alberta. My check ride was fairly uneventful until the pilot checking me out decided it would be a good idea to check my "bush sense" and asked me to enter an extremely tight confined area (even for an R22) with tonnes of overhanging dead fall, and tonnes of tree stumps. I said no initially, however he explained exactly how he wanted it done and that he wanted me to at least make an effort so after a few dummy runs in we went. Pucker factor of about 8....
After that I think he just got bored and he decided to demo OGE zero speed auto's and wrapped it all up with a demonstration of Vortex Ring State at altitude. It was needless to say an enlightening experience, but not an enjoyable one. In the end it was nice to see what the aircraft could do but it also gave me a healthy respect for staying within the flight envelope. Who knows maybe that flight saved my life once or twice?