The Plot: Helena, ward of the Countess of Rossillion (Marsha Mason, left), is in love with military man Bertram of Rossillion (Tony Roach, right), but he’s not into it, even when she wins his hand in marriage as a favor from the king.

In the never-ending quest to say something new about the plays of William Shakespeare, scholars have categorized and recategorized the 38 works: You’ve got your comedies and tragedies, your histories, romances, apocrypha and your “problem plays.” With the Shakespeare Theatre Company restaging the hard-to-pigeonhole “All’s Well That Ends Well” for its annual Free For All, we asked Shakespeare scholar, author and University of Maryland professor Michael Olmert for a crash course in the Bard’s complexities.

“All’s Well That Ends Well” is often categorized as a “problem play.” What makes a play a problem?
People have always wanted to put Shakespeare’s plays in two categories: comedies or tragedies. But there are, depending on how you’re counting, four to eight plays that are … problematic. They end well, but the solution to the dramatic problem was not quite ethical — which certainly is the case in “All’s Well That Ends Well.”

So, do you think it’s fair to call it that?
People don’t say that anymore. There’s no perfect play — and the problem plays are more interesting to us! They’re more ambiguous and less morally certain. We just watch human beings get themselves into — and not quite out of — moral dilemmas.

The play gets resolved so strangely. It’s hard for modern audiences to see the ending as “happy” the way Shakespeare’s contemporaries would have, even though there’s a wedding.
I think Shakespeare was smart enough to have [the wedding] in there as a little time bomb. “You’re free to be happy … now.” I’ve been to wedding receptions and danced and eaten the cake, and at the same time saying, “This isn’t gonna work out.” We’ve all done that, and not because we had a couple of drinks. Shakespeare wants that [doubt] to live in your head, I think. Great art does live with you.

But it’s all so disconcerting!
These plays are poems, most of them. For poems to be good, they have to suggest more than they say. The endings can do that, too. Watch the fireworks, have a dance, have a cuddle, feel good — and then drive home in silence.

Shakespeare Theatre’s Sidney Harman Hall, 610 F St. NW; through Wed., free; 202-547-1122. (Gallery Place)