Arts & Entertainment
Wit, Deception and a Modern Spin: ‘The Merry Wives of Windsor’ Reimagined on a Chicago Stage
Shakespeare’s most raucous comedy, “The Merry Wives of Windsor,” comes to life at Chicago Shakespeare Theater, featuring Ora Jones (Mistress Page), Jason Simoon (Falstaff), Rohan Ryhs Degala (Robin Page) and Issy van Randwyck (Mistress Ford). Directed by Phillip Breen, running in the Courtyard Theater, April 2-May 3, 2026. (Kyle Flubacker)
An overly confident, disreputable knight tries to win the romantic affections of two married women in high-society England in a bid for financial gain. It’s a plan the knight, Falstaff, considers fool-proof as he, of course, must be smarter than his two targets. The underestimated wives, however — Mistress Ford and Mistress Page — learn of the plot and devise a plan of their own to deceive and humiliate the trickster.
That’s the sitcom-esque storyline of Shakespeare’s “The Merry Wives of Windsor,” the 400-year-old comedy now playing at Chicago Shakespeare Theater with a modern spin. Instead of a 17th-century backdrop, it’s 2012 while Queen Elizabeth II is still alive, and the characters are in modern dress and living in Tudor houses.
“It hasn’t always resonated with people for the last 400 years,” said director Phillip Breen, noting that the play is often considered in literary circles to be one of the worst of Shakespeare’s comedies. It has fallen in and out of favor throughout the years. “I think comedy on some level relies on transgression and taboo, and I think there’s a lot of transgression and taboo subjects in ‘The Merry Wives of Windsor’ such as class, money, the fake of masculinity, sex among the middle-aged, female desire and so on and so on. It never fails to strike a chord.”
People are always looking to set Shakespearean plays in periods of “great consequence,” said Breen, who directed “The Merry Wives of Windsor” once before at the Royal Shakespeare Theatre in Stratford-upon-Avon following the London Olympics in 2012.
“There was a sense of the Olympics being that last major progressive cultural moment, and in this period afterwards, the beginning of something a little bit darker,” Breen said. “The optimism of the period that the production first came from was very palpable.”
Shakespeare’s most raucous comedy, “The Merry Wives of Windsor,” comes to life at Chicago Shakespeare Theater, featuring Jason Simon as Falstaff and Ora Jones as Mistress Page. Directed by Phillip Breen, running in the Courtyard Theater, April 2-May 3, 2026. (Kyle Flubacker)
The thing about classics, though, is they’re always relevant.
“There have always been bad old men with delusions of their own sexual attractiveness in the world,” Breen said. “Obviously, that’s come into a much sharper focus for lots and lots of reasons, not least with, you know, in the run up to the 2016 election and the ‘Access Hollywood’ tapes when the president was recorded saying some pretty off-color things. That stuff does come into a kind of a sharper focus, as does the treatment of outsiders. Then things that are eternal — parents with money wanting to find the right husband-slash-wives for their children, education, boredom in marriages in one’s middle age, coming to terms with one’s own failing body, … maybe just maybe some of it is a bit sharper and a bit crueler.”
Contemporary Culture
Like so many of Shakespeare’s works, elements of “The Merry Wives of Windsor” are now intertwined in mainstream culture and media. The phrase “the world is my oyster” comes from the play, for instance, and “what the dickens!” has become a popular exclamation.
In the play, Falstaff is a loud, boisterous man who thinks too highly of himself. That archetype is still seen today in characters like Cliff Clavin from “Cheers,” Frank Reynolds of “It’s Always Sunny in Philadelphia” and Newman of “Seinfeld.”
For actor Jason Simon, portraying Falstaff is a dream come true.
“As a character actor, it’s a wonderful blessing because it means that you are now going from being the side character to being the leading man, if you will, although a bit of a defunct leading man, or I should say a very flawed leading man. Very funny, too,” said Simon, who played Falstaff previously in the Henry plays and is taking him on in the “Merry Wives” for the first time.
Shakespeare’s most raucous comedy, “The Merry Wives of Windsor,” comes to life at Chicago Shakespeare Theater, featuring Jason Simoon as Falstaff (center), along with Teddy Gales (Bardolph), Zach Bloomfield (Nym), Rohan Rhys Degala (Robin Page), Bret Tuomi (Host of the Garter Inn) and Colin Huerta (Pistol). Directed by Phillip Breen, running in the Courtyard Theater, April 2-May 3, 2026. (Kyle Flubacker)
Queen Elizabeth I enjoyed the character of Falstaff in the Henry plays so much that she commissioned Shakespeare to write a story with him at the center, falling in love.
“The Merry Wives of Windsor” was written 14 days later.
The haste with which it was written also lends itself to the play’s criticisms — as well as Shakespeare’s experimentation with language and structure, abandoning blank verse for prose.
A modern critique centers on whether the play is inherently fatphobic. Simon doesn’t discount that as a valid concern.
“Most of the time they are discussing the person, and the verbiage that they use is what we would consider very fatphobic, but really at the heart of what they’re all saying is, like — the audacity of this outsider to try and come in and basically try and break up our marriage is incredible,” Simon said.
Falstaff, however, is not without depth. In a famous monologue, he compares himself to the Roman god of the sky, Jove, or Jupiter — once again proving his own audaciousness with rather beautiful language.
Understanding Shakespeare
The audience is an integral part of the show for a couple of reasons. For one, comedies are pretty beholden to viewers’ reactions and response to the absurdity taking place on stage. Second, the characters break the fourth wall, the invisible barrier between the imaginary and reality to speak directly to onlookers.
“They (the audience) are our witnesses to this, and it’s fun to be able to look at them and say, ‘Do you see what I mean? Do you understand what I’m saying?’ Because they do. They really do,” said Ora Jones, who performs the role of Mistress Page.
Jones’ onstage partner in crime, Issy van Randwyck who plays Mistress Ford, have an electric comedic chemistry together on and off the stage. In an interview with WTTW News, Jones and van Randwyck questioned how they were able to stop from laughing at each during their duos’ onstage hijinks.
Shakespeare’s most raucous comedy, “The Merry Wives of Windsor,” comes to life at Chicago Shakespeare Theater, featuring Issy van Randwyck as Mistress Ford. Directed by Phillip Breen, running in the Courtyard Theater, April 2-May 3, 2026. (Kyle Flubacker)
During one popular scene, the wives lure Falstaff to Mistress Ford’s home while her husband is away and plan to hide him in a laundry basket before Ford’s jealous husband returns home. The plan works as the clumsy knight climbs into the basket full of dirty clothes before the servants are directed to take the basket full of clothes (and Falstaff) and dump it into the Thames River.
If some of the language is confusing to some audience members, the heightened physical comedy helps put the story back into perspective.
“Remember, when this was written, people would go to an execution or a hanging for an afternoon’s entertainment,” van Randwyck said. “We now go to see the Cubs play or go and see the Bears. But at that time, they thought seeing people hurt was a great sport. Now people watch ‘Friends’ or you watch any of those sitcoms. People love schtick. It makes people laugh and it takes them out of whatever misery they’re in.”
How Women Are Represented
Some critics of “The Merry Wives of Windsor” think the titular wives fail to subvert traditional gender norms of the time. Others view it differently, as more of a progressive nod that shows women are funny and witty enough to engineer tricks to outsmart and prank a man.
“It’s a great feminist piece,” van Randwyck said, “because the women basically are the brains behind the whole thing — even the final cut is all their idea.”
“(Mistress Page’s husband) lives in a constant state of incredulity about his wife and what I’m able to accomplish,” Jones said. “He actually says to Falstaff, ‘Don’t feel so bad. Come on over. We’re going to have a big party at my house. We’re all going to laugh at my wife.’ So, yes, it’s an evening of, ‘No, you didn’t.’ ‘Yes, I did.’ ‘How are you going to do that?’ ‘Watch me.’”
“The Merry Wives of Windsor” plays at the Chicago Shakespeare Theater through May 3.
WTTW News arts coverage is supported by the JCS Arts, Health & Education Fund of the DuPage Foundation.
