Probably the time I dressed up as Captain Jack......Daniels (Jack Sparrow) on my last deployment in the Navy. We were at sea on Halloween, so the Captain decided to have a costume contest. I got some of the ladies on board to help me with the makeup.
When it came time for the Captain to judge all the contestants, I swaggered up to him, drew my (toy) cutlass, and challenged him to a duel for the ship.
The look he gave me at first made me think I might have gone too far until he disappeared for a couple minutes and came back with his (real) cutlass, looked at me, smiled, and said 'whenever you're ready'.