Bullet In Head Loophole?

I can’t remember if its a movie or show or what. Someone is forced to kill someone else by putting a bullet in their head/skull. I feel like they might od been some kind of robot because of the absolute need to fulfill this request despite maybe not wanting to(cant remember how they felt but I think they didn’t want to). The person uses a loophole of just placing a bullet in their mouth so that they technically have a bullet in their head and calm the other person down, reassuring them that technically, with the wording, what they needed to do was done.
Please help and thank you!