| | | As ICE roils Chicago, the city is getting the last laugh
Chicago shows how humor can bring people together in a chaotic world.
Theodore R. Johnson
October 29, 2025
Demonstrators protest during the No Kings march on Oct. 18 in Chicago. (Joshua Lott/The Washington Post)
While I was in Chicago recently, an actress with the Second City comedy troupe suddenly stopped a scene about runway models and made eye contact with me. She asked a series of random questions — about my name, the name of a family pet goldfish from years ago, a street I’ve lived on — and then she invited me onstage to join the live improv show. But before doing so, to fit the sketch, she crafted a runway name from my answers, one so ridiculous that a few audience members laughed until their eyes filled with tears: “Ladies and gentlemen,” she said, giggling and motioning me to join her, “I give you Sushi Oakleaf!”
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Immigration and Customs Enforcement was also in town, on orders from the Trump administration. Earlier that day, Illinois Gov. JB Pritzker (D) condemned ICE agents for using tear gas against protesters in Chicago neighborhoods, telling the agency to “ back off.” A few days earlier, a federal judge haddeclared some of the agents’ actions unconstitutional, reminding them that “individuals are allowed to protest. They are allowed to speak. That is guaranteed by the First Amendment to our Constitution.” The agents’ commander responded, “If someone strays into a pepper ball, then that’s on them. Don’t protest and don’t trespass.” At the center of it all is a public resisting what seems like a paramilitary operation happening on their streets. And it’s the furthest thing from funny.
Unbeknownst to the improv troupe, I’d worked with the show’s producers to shape the night’s theme around community and national identity, part of a civic initiative marking the nation’s 250th year. But a week before the show, I wondered if we should postpone it. Maybe better not to pair a night of comedy about America while tragedies unfold in the city. And maybe safer for everyone. Late-night television has shown the risks of getting caught in the crosshairs of a thin-skinned president sensitive to comedic critiques. But in times like these, the last place a polarized public should be is isolated at home; democracies require coming together, for life and for liberty.
And for the pursuit of happiness, too. During World War II, a conflict that killed more people than any other, American celebrities did live entertainment shows in war zones so that service members could share a moment of levity and humanity to cope with life surrounded by danger and atrocity. Nearly a century ago, the Federal Writers’ Project collected narratives from formerly enslaved Black people, which describe, alongside the brutality and injustice, occasional stories of fun at “dances, corn-shuckings, picnics and all kinds of old time affairs … amid much shouting and laughter.” Viktor Frankl, a psychiatrist and Holocaust survivor, wrote in his seminal memoir that humor is “another of the soul’s weapons in the fight for self-preservation.” Prisoners of war have recounted its importance to scholars, with a Vietnam veteran noting in one study that it “allows you to get up every morning and think this isn’t the end of the world.” It is a human impulse to use humor to endure hardship, and it’s also good for the public, improving social cohesion. That makes it fair game for those who would rather see us divided.
Given all of humor’s benefits, a Chicago at violent odds with federal law enforcement was the right place for having a little fun at the country’s expense. The show, titled “America’s Big Beautiful Birthday,” explored different aspects of the country from its founding to current day. Actors cosplaying the Founding Fathers asked the audience to help them enumerate new rights for the Constitution, such as banning slow drivers from the left lane. It lampooned how any issue can become a partisan football on cable news, even yard sales. When one sketch sought to reveal Americans’ lack of civic knowledge by asking a few questions from the citizenship test, the audience got the last laugh — we answered them all correctly.
The following week, Chicago protesters were arrested outside an ICE detention facility. Agents apprehended a man outside a hardware store a day after he’d finished taking his daughter to chemotherapy, according to his attorney, and detained a police officer whose work authorization his employer says was recently renewed by the federal government. Outside of a comedy club located a couple of miles from our event’s venue, bystanders recorded camouflaged agents grabbing a man who witnesses said appeared to be Hispanic just before taking the club’s manager into custody for attempted obstruction. And they allegedly used tear gas near a children’s Halloween parade, sending families into a panic.
Fearless, a neighbor responded that her community would not be chased inside. “Instead,” she said, “we’re keeping ourselves together, resisting with joy.”
This seemed the goal of everyone in the room for the night of improv. Chicagoans laughed alongside actors and audience members from across the country — each seeking a brief escape from a chaotic world. Some of them were worried about the fate of friends, neighbors and co-workers. Fortunately, Sushi Oakleaf took the stage to help find a few moments of levity and humanity. My modeling skills proved atrocious, but the sketch was a riot. And it was protected speech, too, even from a government clad in camouflage and body armor.
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