Anne Hastings: I've written about Anne Hastings (Stafford) before - See my post about William Compton and Anne Hastings - but before she turned Will Compton's head, she gained the affection of the King. There is not much information about this relationship, and there are questions about whether or not the affair even existed, but in any case it was the cause of much scandal at court. Anne, who had recently married George Hastings was said to have been one of the King's first mistresses, starting in 1510. Anne was one of the Duke of Buckingham's sisters, and there is still confusion over whether it was truly Anne, or her sister Elizabeth, who was the mistress of the King. However, more evidence points to Anne, because around 1510 her husband became so angry that he sent her to a convent. As Eustace Chapuys reported, "the husband of that lady went away, carried her off and placed her in a convent sixty miles from here, that no one may see her."
Jane Popincourt: Jane was a French maid-of-honor at the courts of Louis XII and Francois I. She was clearly older than Henry, though there is not much known about her early life or date of birth. During Henry VII's reign, she came to the English court and became a tutor for Henry VIII's two sisters, Mary and Margaret. In 1509, she was appointed as a lady-in-waiting to the new King Henry VIII's wife Queen Katherine of Aragon, and by 1514 rumors were circulating the court that she was the King's mistress. Although little is known about their relationship, it seemed to be pretty brief, Also, despite her being homesick and desiring to return to France, King Louis XII refused to allow such an "immoral woman" to return to his court and attend his new wife (who was Henry VIII's sister, Mary Rose.) Instead, she remained in England until at least 1516 and received a parting gift of money from Henry when she returned to France.
Mary Boleyn: The timing of this affair is unclear, but some say it started around 1521, after Mary Boleyn had married her first husband, William Carey. At this time, Mary had already served at the French court and reportedly embarked on several scandalous affairs, including one with King Francois himself! She was called "The English Mare," and later known as the "Great Prostitute." Typically, it is thought that the affair with King Henry VIII lasted roughly five years and produced two children - a daughter named Catherine and a son named Henry, although the King never acknowledged the son the way he had acknowledged Henry FitzRoy, so it is unclear whether or not this child was truly the King's. It is largely believed that, if he was the King's son, he would have been given titles and honors like Henry FitzRoy, who was made the Duke of Richmond when he was only a toddler. The affair apparently ended before the birth of Henry, and the King moved on to courting Mary's sister, Anne Boleyn.
Mary/Margaret Shelton: It is unclear exactly which Shelton sister was the King's mistress during his marriage to Anne Boleyn, but it seems the many historians lean towards Mary, rather than the modern portrayals of Margaret "Madge" Shelton. She was a cousin of Anne Boleyn and one of her ladies-in-waiting.
** I'd like to note that, although I am not going to discuss them here, both Anne Boleyn and Jane Seymour were also mistresses of King Henry VIII. Although Anne refused his offer to make her his official mistress (and held him off for six years), she was pregnant with her daughter Elizabeth at their wedding, so it is quite clear that she succumbed... Jane, likewise, was Henry's mistress during his marriage to Anne Boleyn, prior to becoming his third wife.**
So there you have it - some of Henry VIII's most famous and well-known mistresses. Don't forget, there could be many more where those came from! It is also important to note that Elizabeth Blount and Mary Boleyn are the only two mistresses who are completely unquestionable by historians. There is enough evidence to guarantee their relationships with the King, but the information about everyone else is a bit fuzzier. Hope you enjoyed this post, and please share any extra facts/opinions!
"A court without ladies is like a garden without flowers..." -King Francois I