3Odette de Pougy
It doesn't get any more wholesome than this: Odette de Pougy was an abbess; the Mother Superior of an abbey of nuns.
In1265, the Pope Urban IV decided to build a church on the site where his father's shoe shop used to be. De Pougy, unaware or not caring that the Pope was her boss, informed him that the property belonged to the abbey and that he could not build there.
Unarmed with the knowledge we have on nuns today, he went ahead with it anyway because he was the freaking Pope. Back then, if you opposed the Pope that was like jabbing God with a sharp stick.
Is it cool with everyone if we just throw in a picture of a hot nun once in a while?
De Pougy didn't give a shit. In true nun fashion (in the context of this article, anyway) she brought armed thugs to the construction site to drive away the Pope's crew. Urban waited two years and tried again, only to witness the return of her personal army. The Pope struck back by excommunicating her entire abbey for 14 years.
He eventually got his church built... but he waited until de Pougy had died to do it.
2Catalina de Erauso
When Catalina de Erauso was 15 and in pre-nun mode, she ran away from the convent where she was raised. It was the first time she had ever seen a street. It goes without saying that like most sheltered kids, the first taste of freedom made her crazy.
She changed her name, dressed in drag and, according to her autobiography, she "hustled, killed, maimed, and wreaked havoc."
After the thug life got old, de Erauso joined the Peruvian army, as a dude. This was all well and good, until she was severely wounded in battle. A priest came to give her last rites and it became that big reveal scene from every transgender comedy ever.
"Nothing to see here, sinner!"
She survived her wounds, though (Medic: "The enemy has a weapon that grows boobies on our men!") and with severely limited options for an alternate career, she went back to the Church and finally became a nun.
It's just that regular nun pictures are so boring.
The Pope even gave her special permission to wear men's clothing, which sounds very progressive until you consider how the Pope dresses.
The shoes. Look at them.