This is the notorious portrait that tricked Henry VIII into marrying his fourth wife, Anne of Cleves.

After divorcing his first wife, offing his second wife, and losing his third wife to childbirth, Henry dispatched Holbein to Germany to paint Anne, bachelorette #4. He gave Holbein express instructions to be brutally honest, though the standard practice was to flatter potential royal brides to seal the deal.

Henry was not amused when he saw the real Anne. While Holbein’s portrait seems to show a very attractive woman and Anne had a reputation as a “middling beauty,” (i.e. not a total hottie but kinda cute), and some even said “every creature rejoiced to behold her,” Henry was the Donald Trump of his time and wouldn’t settle for anything less than a perfect 10. He commented she was “nothing so fair” as her portrait. After their wedding night, Henry said, “I liked her before not well, but now I like her much worse.” All romance, that Henry! He later claimed she had “breasts so slack and other parts of body in such sort that [he] somewhat suspected her virginity.” ‘Cause everyone knows getting laid gives you saggy tits, right?

Henry was one to talk. He had packed on pounds and looked a lot less like Jonathan Rhys Meyers in "The Tudors," and a lot more (at the risk of beating a simile to death) like Donald Trump. In a playful mood, Henry introduced himself to Anne disguised as some random dude, and she “regarded him little.” She was probably relieved that he apparently couldn’t get it up enough to bang her. He claimed they never had sex, though they must have gotten close enough to second base for him to see those offending saggy boobs. Even as he questioned her virginity, he pulled her “V card” to claim non-consummation and get an annulment, which Anne happily agreed to.

Anne got the last laugh. She was poorly educated but she had street-smarts, or rather “court”-smarts. She loved a stiff English beer and a game of cards, and fittingly, she played her hand well. She made off with a hefty annulment settlement, leaving her a rich woman. She and Henry remained good friends, and he often sought her council. She is perhaps his only wife to get a real happy ending, independent and free to pursue her own desires. She outlived Henry and all of his other five wives, dying during the reign of his daughter Mary, just before his daughter Queen Elizabeth I acceded to the throne.

Anne has also lived long in pop culture. Elsa Lanchester played her in "The Private Life of Henry VIII" (1933), opposite her real-life husband Charles Laughton, who won an Oscar as Henry. She went on to appear in an episode of "The Simpsons," and was somewhat inaccurately played by music star Joss Stone in Showtime series "The Tudors."