Charles II

Here we have Charles II. It's his birthday (or was yesterday); he's 380.

Charles II's father was deposed and executed. Oliver Cromwell was in charge during that period. After Cromwell died, people decided they wanted the monarchy back and Charles came over from France to take the throne.

He was married to a Princess, but had tons of mistresses. He had sixteen acknowledged illegetitmate children, and dozens more he didn't acknowledge. He liked actresses, like Nell Gwyn, who was one of the wittiest and most fun royal mistresses of all time.

Charles II never had kids with his wife, but he had plenty with other women to the point that Princess Diana was descended from him in multiple ways. He had a lot of well known descendants, and some less well known ones. Hell, if you have any British ancestry there's a good chance you might be descended from him.

Charles's friends once played a prank on him where they took him for a night out at a brothel and then stole his money. He had to track down one of his girlfriends to get his money.

His wife, Catherine of Braganza, once walked into his bedroom to talk to him. After a few minutes of discussion, she noticed a woman's slipper next to his bed. She picked it up, gave him a dirty look and said: "I will leave you now so you can get back to the poor fool who's slipper this is."