Some of Shakespeare's early plays were very successful, particularly the Henry VI plays and Titus Andronicus. He may have written some clunkers before that which we don't know about, so it is difficult to say that he was immediately successful.
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Shakespeare was alive and writing in both the sixteenth and seventeenth centuries.
i think so
Shakespeare got much of his information from the writings of Plutarch. But remember, Shakespeare was not a historian, he was a playwright. He used artistic licence to change the characters and their motivations in order to write a good play.
We presume that Shakespeare did not start writing plays until after he moved to London to make a living in the entertainment world.