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Playing the Fool
She's a fool. And proud of it. Meet the city's official Municipal Jester.

Photo by Steven Bourelle

There are very few people in this life who enjoy being called a fool. Ann-Elizabeth Shapera is one of them. Originally from Geneva, Ill., and often found in the smoky jazz joints of Chicago during her childhood (her dad is veteran bassist Dan Shapera), she’s been appearing at fairs and fests as Jane the Phoole (her interpretation of Queen Elizabeth I’s court jester) for the past 20 years. But her crowning achievement may have arrived Sept. 21, 2004, when, by official decree – in much the same way the Common Council recognizes April 14 as “Milwaukee Day” – she was named the city’s official Municipal Jester. By day, she’s a mild-mannered purchasing agent for the city. She says it gives her brain a break from finding new ways to say “bad monkey” (more on that later). But no matter what role she’s in, she’s certainly no half-wit.

How did you break into the jester game?
I started performing at the Bristol Renaissance Fair in 1990 while a freshman at Northern Illinois University. There was a grad student in my program who said, “You know, you’re kind of loud and hilarious and should be outside.” And I’m like, “Excuse me?” She said, “No, you gotta see this gig that I got.” I went and auditioned, and I never looked back. 

And how did that lead to becoming Milwaukee’s official jester?
There is a family that has lived in the same castle in the United Kingdom for hundreds of years. In the 16th century, in Shakespeare’s time, that family had a jester named Thomas Skelton, who was so famous and infamous for his nefarious deeds that he became the reason we have the word “tomfoolery” today. About 13 years ago, the family decided to increase tourism at their castle by having an international jester tournament. They approached me to be one of the first American competitors and the first female competitor. Because the current city clerk, Jim Owczarski, used to perform at the Bristol Renaissance Fair with me, he said, “Well, you’re going to need some official cred.” So he approached the common council, the resolution was drafted, and that’s me today.

Is it a lifetime appointment?
It is. And it’s totally pro bono. I receive zero compensation. It’s important that the citizens of Milwaukee realize that zero dollars of their tax money go to my follies. 

What are your duties?
I don’t really have any, which is fitting, because if you look throughout jester history, there wasn’t really a specific job description. Fools and jesters did everything from being members of the royal household to being royal grooms to being advisers, being entertainers to being best friends. So while I do all of those things, there isn’t any particular one that I’m commanded to do. 

Are you tasked with entertaining our local politicians?
No, no, no, no. One thing about the actual function of a court jester is that we tell the truth. Like, what’s a good example? Stephen Colbert, he’s a pretty famous jester. Or Jon Stewart, he’s an excellent court jester. They tell the truth through comedy. And people are a lot more likely to hear the truth through comedy than they are through just getting it hammered into their heads. So unfortunately, in our culture, it’s the people who most need to hear the truth who do not retain people to tell it. I tend to stay as far away from politicians as I possibly can. And I think they appreciate that. 

Which Milwaukee politician most resembles a fool?
Oh, see that’s hard, because in my mind, fool is a positive thing. It’s a level of honesty and directness and not having ambition in the sense of not wanting to take advantage of other people. So that’s tough. I’m gonna back delicately away from that question.

Out of your bag of tricks, what’s your favorite?
I started collecting the phrase “bad monkey” in foreign languages. I’ve learned how to say it in 152 different languages now. My goal is to get to 200 by September. 

Do you sport a costume? 
I do. I have an entire basement full of costumes. I quickly learned that you can either pay somebody $3,000 to get a costume that doesn’t quite fit right. Or you can learn to make it yourself and have it fit you perfectly and be ridiculously beautiful. All of my fabric is from Mood Designer Fabrics in New York, because, why not? That’s the store that supplies “Project Runway.” 

What are the perks to being the city’s jester?
They are whatever I make them. If there’s a parade that I want to be in anywhere in the United States, I say, “Hey, I’m the official jester of the city of Milwaukee.” And all of a sudden, people are going crazy, saying, “Wow, Milwaukee has a jester. What a civilized place.”





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