It’s the morning after the midterm election and comedian Matthew Filipowicz has been given a gift for a show he’s organized monthly for the last ten years, Laughing Liberally Milwaukee; a blue tsunami that swept the country coast-to-coast the day before.
“It’s clear it’s going to be a giant party, because we have a lot to celebrate here,” Filipowicz remarked. But over the last ten it feels like there’s been more commiseration than celebration.
Filipowicz started producing his monthly comedy show, when he moved to Milwaukee. Featuring stand-up from comedians around the Midwest, attendees can expect sketches and an interview with a local activist or politicians, alongside stand-up routines.
Laughing Liberally celebrates their 10th Anniversary show, this Saturday, Nov. 14 at ComedySportz (420 S. 1st Street) and will feature Ton Johnson, who performed at the first Laughing Liberally Milwaukee show, as well as Syed Hasnain, Breanne Wilhite, Chloe Mikala, and the show’s resident sketch comedy group The Accountants of Homeland Security. The interview portion will feature author and historian Rick Perlstein, best-selling author of books like Nixonland and The Invisible Bridge.
Celebrate this year’s winners of the Betty Awards!
Ten years ago, Filipowicz had been moving around, living in Chicago and Boston, participating in both cities with an organization called Living Liberally. “Part of the organization is Drinking Liberally, which is our most common thing with chapters around the country; it’s like a social club,” Filipowicz said.
After his wife got a job in Milwaukee, Filipowicz picked up where he left off in Boston, starting a Drinking Liberally chapter in town and producing the show. With the help of some local talent and a new home in ComedySportz.
“Being that Wisconsin is a purple state, I thought the show would be successful here, the audience might be more appreciative than Boston or Chicago,” Filipowicz said.
He was right. Their first show, the Saturday before the 2016 election that began the Trump era, almost sold out and the comedy roller coaster began.
Filipowicz says the show provides a sense of community.
“I think the audience feels the same way, that you’re not alone — laughter has so much power,” he added.
Looking back over the last ten years, Filipowicz says one of the best shows was the one following the defeat of Scott Walker in 2018.
“That was exceptionally great. It was so damn fun, the crowd was so excited,” he exclaimed.
The hardest show was the one that took place just hours after an assassination attempt against President Donald Trump in Pennsylvania in 2024. The comedians were already at the venue getting set up when the news came in.
“It was like how do you handle that situation,” Filipowicz remarked. “It was hard but it still ended up being an amazing show.”
Looking ahead to 2028, he does worry about a swing back right if Democrats don’t deliver. Regardless, he plans on having the last laugh.
