Henry VIII, Catherine of Aragon and Anne Boleyn

The poster boy for bad breakups, the teenage Henry became king of England in 1509 and soon afterward married his first wife, Catherine of Aragon, the widow of his older brother Arthur. By the mid-1520s Henry had grown unhappy that Catherine hadn’t produced a male heir; although she’d given birth multiple times, only one daughter lived past infancy. Additionally, the Tudor king had become besotted with Anne Boleyn, the sister of one of his mistresses. Intent on tying the knot with Boleyn, Henry, a Catholic, asked Pope Clement VII for an annulment of his first marriage. The pope refused, not wanting to upset Catherine’s nephew, Holy Roman Emperor Charles V. Henry married Anne in 1533 anyway and was excommunicated by the pope. The monarch subsequently had himself declared head of the Church of England and took over the nation’s monasteries, selling off much of the land. Anne, who gave birth to a daughter in 1533, eventually fell out of favor with Henry when she failed to provide him with a son. In 1536, she was found guilty of trumped-up treason charges and beheaded. Henry had four more wives: Jane Seymour, who died shortly after giving birth to a son; Anne of Cleves, whose marriage to Henry was annulled so he could wed wife No. 5; Catherine Howard, who was beheaded for treason and adultery; and Catherine Parr, who avoided the fate of her predecessors and managed to stay married to the king until his death in 1547.