1) Stalls, 2.5G windup turns and -1G pushovers in a 747SP as part of a test program for NASA. We lost $125K worth of access panels that decided to depart the plane over Texas.
2) Very few will understand this one. Pull the curcuit breakers for stick shacker and stick pusher and then do stalls in a Gulfstream III. Having the test pilot tell you "That one almost go away" is not something you ever want to hear.
3) Hands off landings in a various aircraft. Just ride it in and hope for the best.
4) Tell a career Colonel that he is no longer
allowed to fly "my" airplane because he is among the worst pilots I've ever seen. I was 28 running my first flight test program.
5) Landing with blown tires on a Falcon 20. We had a ABS malfunction on takeoff and one tire on each main landing gear strut locked up and burned through. Landing was a bit rough. A video camera on board whited out due to the vibration level.

To qualify this I'm not a pilot. I'm an engineer, I ride in back running a data acquisition system or up front behind the pilots acting as the test coordinator. I have very little control over the surroundings and have to trust the trained monkeys up front. For this I get as a benefit a company paid $100,000 death and dismemberment insurance policy and a salary about 20% below industry norms.