By some accounts Shakespeare was a good-looking, witty young man, probably not unlike Joseph Fiennes's portrayal of him in the 1998 movie Shakespeare in Love.

Shakespeare could be intense, had a real eye for the dramatic in a situation, was extremely knowledgeable about stagecraft, and likely paid great attention to the world and the people around him, initially listening more than talking.

Shakespeare would likely have been the quiet one in a crowd at first, the one who sat in the corner entertaining himself and perhaps a friend or two by watching everyone coming and going in a room and making pithy, witty comments, probably in a low voice. But once the party got going, he was likely just as loud and passionate as others. Pity the poor man who had to get into an argument with Shakespeare. A nimble mind, a way with words, and a sharp tongue no doubt helped him win a lot more arguments than perhaps he should have won.

What Did Shakespeare Look Like?

We have all seen his likeness; the portrait of the bald man with a wispy mustache and prickly hair under his lip, big black eyes staring at — nothing. This image is from the Droeshout Engraving and first appeared on the title page of the First Folio, the original collection of Shakespeare's plays. Yet, is it a correct representation of the man? The engraver, Martin Droeshout, was fifteen when Shakespeare died, so the portrait certainly didn't come from life, nor do we know if the engraver and playwright ever met.

The Chandos portrait is far more romantic, offering an idealized face of the playwright wearing a gold earring. Richard Burbage, the best-known actor in Shakespeare's company and an artist, was once thought to have painted it, though the more likely artist is one John Taylor. It is called the Chandos portrait because it eventually came to be in the possession of the Duke of Chandos.

The worst likeness is no doubt the Janssen bust, which is in Holy Trinity Church in Stratford and is placed near Shakespeare's tomb. He is shown as a bloated figure, the features puffy, which could be a reflection of his illness in the last years of his life.

Shakespeare's Fees from His Writing

Most of the records that mention Shakespeare deal with lawsuits. He was a businessman and the theater was the movie house of its time. Shakespeare was both a “sharer” in the acting company and a “housekeeper,” or part owner of the theater building itself. As such, he received 10 percent of all profits. He was careful with his money (perhaps as a result of lessons learned from his father's misfortunes). He earned fees not only from writing plays and from their production, but also from investments in real estate. He did not own his plays — those were owned by the Lord Chamberlain's Men, later known as the King's Men. But since Shakespeare gained from the company's buying his play as well as producing it, his profit was greater than those playwrights who were not sharers. He became a very wealthy man.

We have no evidence that he traveled abroad, although it is certainly possible given his knowledge of other countries and the things he wrote about in his plays.

Was Shakespeare a Womanizer?

Certainly the movie Shakespeare in Love showed him involved in an amorous relationship. One can easily suppose that as an actor he had access to many sexual companions. A law student named John Manningham wrote this in his diary in 1601 when Shakespeare was age thirty-six:

Upon a time when Burbage played Richard III there was a citizen grew so far in liking him that, before she went from the play, she appointed him to come that night unto her by the name of Richard the Third. Shakespeare, overhearing their conclusion, went before, was entertained and at his game ere Burbage came. Then, message being brought that Richard the Third was at the door, Shakespeare caused return to be made that William the Conqueror was before Richard the Third.

This anecdote may only be that — a funny story. But what is known to be fact is that Shakespeare addresses most of his love sonnets to a young man and some to a “dark lady.” What those facts mean is more debatable.

Performing for Royalty

Shakespeare wrote and performed for both Queen Elizabeth and her successor, King James. He also had a royal patron. These circumstances no doubt helped him write convincingly about royalty. It is not a stretch of the imagination to think that as the leading playwright and poet of his time, he was often in the company of leading political and social figures of the time, whether aristocrats or not.

In 1603, Queen Elizabeth I died and James VI of Scotland became James I of England. He took Burbage and company under his sponsorship, renaming the company the King's Men. James commanded more court productions from this premier troupe than did Queen Elizabeth. For him in particular, Shakespeare wrote “that Scottish play,” Macbeth.