I'll play ....
I was Legal Officer in my squadron, so I had plenty of experience with dumba$$ stories, but the funniest (?) I ever heard was when I was attending the Navy's Legal Officer School in Newport. We had a female Marine Major , former Military Judge, teaching one of the classes, and she kept hinting that maybe she would tell us the story about the wierdest case she handled. Finally, near the end of the three week course, we were all out at a local watering hole, and she had a few ...and told us the story of the young enlisted Marine (of course ..)who appeared before her on charges that he was attempting to (um how do I put this more tactfully than Major did --she was pretty salty !) engage in sexual relations with the tail pipe of a vehicle in the motor pool.
I had one young Airman who was always in trouble.. He was a good kid, but his brains were below his waist. I remember sitting down with him after yet another mast and telling him I'd buy him a beer if he made it through his enlistment.
My favorite was a young female Airman in my Division after I turned over Legal Officer . She was continuously in trouble for petty things, always bucking the system. When she protested the evaluation with a do not promote recommendation, Skipper directed me to look deeper into her background -- she had 3+ years of ROTC at a good college in her record, so I called the ROTC unit and spoke with an officer there who looked up her record - her evaluations there (which resulted in her being dropped from the program right before commissioning) were almost identical to what I had written in the eval., something along the lines of "inability to conform to military standards.." Her performance and conduct got worse over time, and at one point got court martialed for threatening the Legal Officer. (She declined Mast). Last I heard of her, I had to prepare the response to a congressional inquiry -- she had written her Congressman complaining that she was being held in the Philly Brig "against her will." I think I started my response to the Congressman's office with "Most people in the Brig are held against their will....but here's why Airman ___ is there...:"