While still in his early teens, he scrawled on a textbook "Thys Boke Is Myne Prynce Henry" - "This Book Is Mine Prince Henry" - in letters almost an inch high.
"He was a very arrogant young man," said Richard Kuhta, curator of an exhibit that features the textbook. The show opens Wednesday at the Folger Shakespeare Library.
Henry's behavior got more aggressive as he got older. He married six wives, beheaded two of them, broke his country away from the Roman Catholic church and set himself up as head of the Church of England.
The exhibit, titled after Prince Henry's scrawl "Thys Boke Is Myne," is about the owners of books and what they do with them.
The display has 114 items, including the dog-eared copy of Shakespeare's Sonnets that Walt Whitman carried around but did not write in. There's also a copy of "Shakespeare in Harlem" by black American poet Langston Hughes, with a poem handwritten in it by Hughes himself.
"Somehow we know more about these human beings by the way they wrote in their books," Kuhta said.
One early book collector, more generous than Henry, wrote at the top of the title page of his books that they belonged to him, adding at the bottom "and to his friends."
Another inscription in the exhibit comes from a prayer book given to Henry by one of his wives, Anne of Cleves. Before the wedding, she wrote gently on the last page: "I biseche (beseech) your grace humbly, When ye loke (look) on thys (this) remember me."
Anne was the daughter of the Duke of Cleves, who ruled what was then an independent Protestant duchy. Henry was convinced he needed its help to counter a Catholic alliance between France and the Holy Roman Empire, so he married Anne, sight unseen.
When Anne arrived in England, Henry found her ugly. He had the marriage annulled six months later and executed the adviser who had urged it.
Henry's selfishness is a theme in a play that Shakespeare wrote long after the king's death. "King Henry the Eighth," was Shakespeare's last work, a collaboration with John Fletcher.
In Shakespeare's day - the 1500s and 1600s - collectors often added a motto to their signature in a book. The poet John Donne used an enigmatic biblical reference that he took from an earlier poet: "I served for Rachel, not for Leah."
It recalls the story of Jacob in the Old Testament who wanted to marry Rachel. To get her he worked seven years for her father Laban, only to be tricked into taking her elder sister Leah instead. To get Rachel, he had to work another seven years.
Kuhta said he had no idea why Donne chose the motto, which is among the items on display.
A more recent contributor to the Folger collection is Franklin D. Roosevelt. On the first volume of a Shakespeare set, the president wrote in the midst of World War II:
"This set was given by me to my mother Sarah Delano Roosevelt about 1900 and was in the room in Hyde Park until her death in 1941, when it came back to me."
By Carl Hartman