Yep, back in the 1960s with a High Standard .22 pistol. Was trout fishing up on the Rim at Tom's Creek in Arizona, little sidewinder buzz tail rattled at me. I pulled the pistol, jacked one in and blew it's head off. Had the holster on the belt, but in my hip pocket, and there things went wrong. It was the wife's gun and I had told her a 100 times that due to the phony easily disengaged safety, never carry it with a round in the chamber, but forgot my own advice. I reached around to put pistol back into the holster, the holster hold down strap got into the trigger guard, when pistol did not go in, I manipulated it back and forth, taking it off safe, shoved down and "BAM." Bullet entered high on back of my thigh, traveled through meat 16 inches and lodged behind the knee. It hurt like hell after a few minutes, was told by the doctor who took it out at the Payson hospital I was lucky, (didn't feel like it) the bullet was resting between the main nerve column and artery. Was off work for several weeks.
I learned two things that day, a .22 rimfire has very good penetration, and stupidity with guns can get someone hurt.