Your Regional Guide To The Performing Arts

Celebrating 10 Years of Milwaukee's Shakespeare in the Park

Celebrating 10 Years of Milwaukee's Shakespeare in the Park
Photo Credit: Ron Scot Fry as William Shakespeare in "To Be! Shakespeare Here And Now" at Winnebago Lutheran Academy. Photo by Justin Connelly.

Much like performing outdoors, the past 10 years of Optimist Theatre have been unpredictable.

“It’s just been a runaway train that I’ve been trying to get in front of,” says Susan Scot Fry, co-founder of Optimist Theatre, which produces Milwaukee’s free Shakespeare in the Park. “I think I’m starting to get in front of it, but barely.”

Fry and her team started pursuing Shakespeare in the Park in 2008 during the height of the recession. The name Optimist Theatre served as a reminder to stay positive, despite the challenging time to tackle such an ambitious project.

“Shakespeare in the park is a cultural institution,” Fry says. “Everyone has one, especially a metro our size. I got a focus group of people together to ask if this would be a good idea for Milwaukee. Everyone was like ‘we don’t have a Shakespeare in the Park? How did that happen?’”

Angela Iannone and James Pickering in "The Tempest." Photo by Frank Miller.

After submitting a grant application to launch the program, the folks with Optimist Theatre sat in on a review meeting with the Wisconsin Arts Board, just to hear their proposal ripped apart.

“It was horribly written, it was awful, but you have to do it to get better,” Fry says. “At one point, because it was obvious what we were trying to accomplish and that we had the expertise and team to do it, a gentleman at the concluding of the review said, ‘I don’t know if they can pull this off, but if they can, we have to have our name on it.’”

Milwaukee’s first Shakespeare in the Park commenced with
The Tempest, starring established local actors James Pickering, Angela Iannone and Tom Reed in 2010. For the first three years, Optimist Theatre held their productions on green space at Alverno College, followed by four seasons at Kadish Park’s Selig-Joseph-Folz Amphitheater.

"As You Like It" (2013) at Kadish Park. Photo by Jill Newton Moore.

Today, Optimist Theatre prepares for its third season performing at the Marcus Center for the Arts’ Peck Pavilion. No longer does the company need to drag port-o-johns up the hill of Kadish Park, or cart costumes, lighting and sound equipment to storage at the beginning and end of each performance.

“The Peck is like luxury,” Fry says. “You would think of bathrooms or dressing rooms as something you could take for granted, but you can’t.”

Thanks to the Peck Pavilion’s amenities, Optimist Theatre has been able to focus additional efforts on community outreach. Optimist’s educational program,
To Be! Shakespeare Here And Now, features Fry’s husband, Ron Fry, as The Bard in a dynamic one-man show that travels to schools, libraries and other organizations.

Optimist’s latest workshop program,
Shakespeare Inspires: Stories from the City, debuted in summer 2018. Through the program, young people explore some of the questionable choices made by Shakespeare’s characters, while relating these decisions back to similar circumstance in their own lives.

James Pickering and Kat Wodtke in "King Lear" (2018). Photo by Michelle Owczarski.


This year’s production, The Comedy of Errors, again features James Pickering, along with his wife Tami Workentin and fellow veteran performer Robert Spencer. Fry says Optimist strives to cast emerging talent alongside these accomplished performers.


“We are going to introduce some people that I think audiences are going to go ‘wow! I had no idea they were here.’” Fry says. “The thing that we are doing with our equity actors this year is they are playing multiple roles. They are going to be in a lot of scenes with these younger actors and they are going to go help drive those scenes. Those actors are going to learn so much by working directly with the veterans.”

The Comedy of Errors features two sets of twins, a pair of masters and a pair of slaves, separated by shipwreck in infancy. As one of Shakespeare’s early farces, it relies on puns and mistaken identity for its humor.


“Now that we have nine seasons under our belts we can kind of see some trends,” Fry notes. “When we do a comedy we get younger audience members. They are willing to take a chance and go for it. Every year we get someone who has never been to the theater before. The younger audiences are going to get the most out of what we are trying to accomplish from a bigger mission perspective.”


The Comedy of Errors, presented by Optimist Theatre, runs June 27 – July 13 at the Marcus Center for the Performing Arts’ Peck Pavilion. Admission is free to the public.

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