Us@250 Dispatch: Chicago, Illinois

James Madison raised an imaginary pint to his fellow Founding Fathers on stage, toasting a successfully completed U.S. Constitution. But then he paused with sudden alarm, palm to forehead: “I just remembered! The Bill of Rights is due tomorrow!”

“Bah,” Thomas Jefferson interjected. “We can just write something down.” He gestured to the audience, breaking the fourth wall: “Surely, they’ll change it in a few years.”

We all laughed as the founders carried on, fudging their way through the first ten amendments like college students working on a term paper at the last minute.

These Founding Fathers were cast members from legendary comedy troupe The Second City, and on a recent autumn evening in Chicago’s Old Town, they aimed for the absurdities of the Great Experiment. The performance, entitled America’s Big Beautiful Birthday, included a mix of best-of sketches and improv skits, reminding us that “one of the pillars of American society is the freedom to laugh at ourselves,” as audience member Rengin Altay told me. Altay, an actor herself and longtime Chicago resident with a quick sardonic wit, added, “Or at least to grin and bear it.”

Earlier that day, I’d scanned the news while taking the South Shore Line commuter rail over from my home in Indiana. In Chicago, the afternoon before, masked federal agents in an unmarked vehicle teargassed a neighborhood block on the city’s East Side following a high-speed car chase and crash on a residential street. This was just the latest terrifying episode among dozens that had taken place in the city since immigration police operations had surged in September. I read about how, just the night before, hundreds in Chicago’s Northwest Side had volunteered to participate in “Whistlemania,” where emergency whistles and instruction manuals were packaged for distribution to community members, items that could be used to warn others of dubious federal activities.

Outside of Millennium Station, Lake Michigan was a frothy seafoam green beneath the gray sky, and the day was damp and drizzling. After dark, the marquee lights at the UP Comedy Club felt welcoming. Inside, I sat beside Rengin and her husband, the author Miles Harvey. “I could use a laugh tonight,” Miles said before the show.

And we did laugh, at ourselves and at our country’s ability to argue about everything—such as estate sale shopping, a topic suggested by an audience member in one of the night’s best sketches. The weekend hobby became a political football across a set of improvised scenes that zigzagged from adoring MSNBC news desks and TikTok videos to disapproving Fox News hosts and a critical song sung by fictional country music star “Keith Toby.” But once reporters caught the singer estate sale shopping himself, he sang a patriotic ballad in favor of it. And suddenly, the cable news hosts changed their tune—MSNBC denigrated the hobby while the Fox News crowd praised it. By the end of the sketch, the audience member who’d suggested estate sale shopping in the first place—coincidentally, New America staff member Angela Moorman—received some playful scolding by Second City cast member Lexi Alioto: “We asked you for a simple hobby and you gave us something so political it tore this country to shreds!”

We laughed when Cuban-American performer Eddie Mujica, during a send-up of the U.S. Citizenship exam, referred to the Millennium Park sculpture commonly known as “The Bean” as the “big frijole.”

We laughed during a particularly poignant sketch about generational divides, when a father asked his Gen Z son, “Do you like me?”

The son replied, “I love you.”

“I know you love me—that’s an obligation. Do you like me?”

This sketch felt like an of-the-moment echo of that famous father-son scene in August Wilson’s great American play Fences, and it seemed to me that all of us there were able to share in a kind of meaningful regard for a very human moment, for the attempt to bridge the gulf between individual experiences. After a wild scene of teen jargon and dad jokes and awkward vulnerability, the father offered, “I love you, son.” And the son responded, “I like you, too, Dad.”

During intermission Rengin and Miles and I continued to chat. “The obvious thing,” Miles suggested, “is that improv and democracy are about making it up as you go along.”

Rengin pointed out that what the performers were doing was play, but it also had rules. “How well you listen to each other is the most important thing,” she said. The game works best when an actor’s response to another’s offering with the generative, “Yes, and…”

“You have to be willing to make something happen with others,” Miles said.

“Without self-aggrandizement,” Rengin added.

In the final sketch of the night, the Second City actors improvised an absurdist day-in-the-life of audience member Ben, a Chicago bartender, wherein the cast stretched Ben’s responses to their interview questions to comedic extremes. His “fun and energetic” friends became insufferably exuberant, for instance. Ben's life philosophy became the very last line of the sketch: “I’m just figuring things out as I go.”

Afterwards, the audience milled about in the lobby, discussing their favorite moments of the performance. But there were also conversations about the masked federal agents showing up to individuals’ workplaces or hassling their students at school. One attendee described hearing the three-note blasts of emergency whistles that had rung out in their neighborhood.

While walking back to my hotel, the show’s last line reminded me of Katherine Anne Porter's classic essay from 1950, “The Future Is Now.” In it, she wrestles with despair over the ominous promise of nuclear proliferation, but she ends with a sort of grimly stubborn optimism:

“And yet it may be that what we have is a world not on the verge of flying apart, but an uncreated one—still in shapeless fragments waiting to be put together properly. I imagine that when we want something better, we may have it: at perhaps no greater price than we have already paid for the worse.”

I took the train downtown in the morning. The day was beautiful and bright. A steep concrete stairwell leads into the Millennium Station underground. At the bottom, an elderly woman was struggling to get her luggage over the very first step. By the time I’d descended the stairs, a young stranger had already offered her a hand. She thanked him, gripped his forearm. “I got you,” he said, and they climbed the stairs together.