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The movie is about the sisters, Anne Boleyn (Natalie Portman) and Mary Boleyn (Scarlett Johansson), who are both fighting for the affection of King Henry VIII (Eric Bana). Although initially reluctant to become Henry's mistress, Mary comes to fall for the King, while Anne is only interested in securing her own status. Their father, Sir Thomas Boleyn, and uncle, the Duke of Norfolk, engineer the sisters' coming to Henry's attention in the first place, capitalizing on his dissatisfaction with his wife, Catherine of Aragon, who has failed to bear him a living son. The ambitious men seek their own gain in having a female relative as the King's mistress. First they select Anne, who is older, more ambitious and unmarried, and arrange for her to catch Henry's eye, but when Henry is injured in a hunting accident, indirectly caused by Anne, they have Mary nurse him.

Rebellious Anne then marries nobleman Henry Percy secretly and confides in her brother George. George then tells Mary, but is confused as she is not happy about the marriage. Worried that Anne will ruin her reputation in marrying a nobleman without the King's consent, she tells her father and Uncle. They tell Anne that the marriage has to remain secret as Henry Percy is also betrothed to another and is set to marry another woman. The marriage of a nobleman is to be decided by the state. Anne argues that what is done before God cannot be undone, and that the marriage had been consummated. This angers Anne's father and uncle and she is sent away in exile to France.

While Anne is sent to France in disgrace, Mary becomes the King's lover; the Boleyns' fortunes seem secure when she becomes pregnant. But when Mary nearly miscarries and is confined to bed rest to protect the baby, Norfolk recalls Anne from France to keep the King's attention from wandering to another rival (such as Jane Seymour). Anne embarks on a successful campaign to attract Henry, showing herself to be more sophisticated and accomplished than she seemed before. By withholding her sexual favors, she ensures Henry's continued interest, finally making him promise never to bed his wife or speak to her sister in exchange for her giving him hope of eventually possessing her. Anne exacts this promise just after Mary gives birth to the much-anticipated son, making her sister's triumph hollow.

The ambitious Anne continues to refuse Henry's advances, until at last he obtains an unpopular divorce from Catherine and promises to marry her instead. The scandal of her brief, secret marriage to the young nobleman Henry Percy threatens the alliance, but Mary, out of loyalty to her family, returns to court and vouches for Anne. Despite the removal of this final obstacle, Anne's manipulations have pushed Henry to his breaking point. He blames Anne for England's schism with the Roman Catholic Church and rapes her. Confused and hurt by the attack, a now-pregnant Anne still goes through with her marriage to Henry and becomes Queen of England. The sisters reach a reconciliation and Mary stays by Anne's side at court. Despite the birth of a healthy daughter, Elizabeth, the royal marriage is unhappy. After Anne miscarries her second child, she becomes desperate and asks her brother, George Boleyn (Jim Sturgess), to try to impregnate her. Disgusted and horrified by Anne's request, Mary again leaves behind the intrigues of court. Anne and George are unable to go through with incest. Nonetheless, George's neglected wife, Jane, sees enough of their encounter to make her suspicious. Her testimony sets off the arrest, trial and, eventually, the execution of both Boleyns. Mary returns to court to plead for her sister's life, and although Henry seems to soften, he permits Anne's beheading to go on. He even warns Mary never to come to court again, because her family's disgrace could result in danger to her as well. Mary fulfills her last promise to Anne and takes care of her infant daughter, who will grow up, the film's epilogue notes, to be the strong and successful heir that Henry always wanted: Elizabeth I.