Second City is on the auction block. Why Chicago has much to lose.

So Second City, Chicago’s beloved comedy theater in Old Town, is up for sale. This has happened once before. But the possible loss of local ownership, or any diminishment of the institution as a whole, should set off alarm bells within the business community, tourism agencies and the offices of both the governor and the mayor. Not to mention the hearts of ordinary Chicagoans.



Keegan-Michael Key et al. posing for the camera: Newly arrived from Detroit, Second City's Keegan-Michael Key creates a Pakistani taxi driver who has turned his Chicago vehicle into a patriotic shrine full of flags and paraphernalia, and who answers awkward questions about his ancestry by turning up the Lee Greenwood or Neil Diamond and lip-syncing.


© Peter Thompson/Chicago Tribune/TNS
Newly arrived from Detroit, Second City’s Keegan-Michael Key creates a Pakistani taxi driver who has turned his Chicago vehicle into a patriotic shrine full of flags and paraphernalia, and who answers awkward questions about his ancestry by turning up the Lee Greenwood or Neil Diamond and lip-syncing.

In America, most entertainment is developed, packaged and produced in either Los Angeles or New York City; the coastal elites designate the rest of the country merely as marketplaces to sell their stuff. Unless some TikTok kid smacks them in the face hard enough to merit a plane ticket to La La Land, or they can use a gritty city as a backdrop for predictable procedural TV shows, they rarely look to the hinterlands for talent, sophisticated ideas or content. Don’t kid yourself otherwise.



a group of people standing next to a sign: Posters at the entrance to Second City on Wells Street in Chicago.


© John J. Kim/Chicago Tribune/TNS
Posters at the entrance to Second City on Wells Street in Chicago.

Second City has consistently bucked that trend over its 60-year history. Its ability to propel young Chicagoans like the brothers Belushi, Keegan-Michael Key, Tina Fey, Amber Ruffin, Stephen Colbert and countless others to international stardom is both singular and well-known. But, throughout that time, it also has operated as a crucial satirical safety valve in which a high-pressured city can let off steam.

At least three generations of Chicagoans, from city and suburbs, have brought their out-of-town visitors to Old Town, and conventioneers have found their way there all on their own. Back when people of different political views could still sit and laugh together — remember? — Chicago came together at crowded tables to poke fun at mayors, aldermen, presidents, activists and cops.

At Rahm Emanuel, Richard J. Daley, Harold Washington. At a Chicagoan named Barack Obama. Immigrant cab drivers weren’t immune. Nor were Lincoln Park yippies turned yuppies. Nor red-lining realtors. And lovable Ale House prophets of all stripes were the preferred philosophers.

Laugh together at subjects such as policing strategies or red-lined neighborhoods? If you are thinking that is just not funny in America anymore, well, that’s part of the reason for the sale.

The pandemic that has closed its theaters — with no clear path to reopening — is a primary cause of trouble. But Second City is also suffering from the great American schism, the internal fury and polarization that has festered over the last four years, with direct encouragement from the top. Satire is on the ropes. A new owner can fix the internal problems, but the American people will have to decide if they ever can laugh together again.

Most of the best content I’ve seen at Second City over the last 25 years, and I’ve never missed a new revue, has drawn from our city’s deepest divisions, fears and insecurities, worked though live and in real time. Second City has not only given Chicago a needed positive brand as a big-shouldered place that can laugh at itself, it has helped keep the city closer together. There have been blind spots and mistakes when it comes to racial equity, diversity and inclusion, and there is plenty of content made in the 1980s and 1990s by famous white alumni that would now make a reasonable person shudder. But that is also true of “Saturday Night Live” and most of the other comedy of that era. And it would be wrong see the sum history of Second City as anything but progressive and positive for Chicago and America.

In recent months, Second City has tried to cast itself as an institution with a tortured racist past that now needs wholesale reinvention. There is truth in that, but it’s also an over-simplification unfair to its often radical founders.

Young people, and those in the media, tend to forget that the Black Panthers hung out there in the 1960s, and that Howard Alk, one of the co-founders with Bernie Sahlins, went on to become an important radical documentary cinematographer whose first subject was Fred Hampton. Jewish intellectuals with links to the University of Chicago dominated the first decades at Second City, but their links with the civil rights movement in Chicago were in excess of most any other arts organization in Chicago. People forget how much Old Town has changed.

In recent years, as New York and Hollywood came calling, much of that Old Town spirit of radicalism was lost. With a pyramid-like training structure that guaranteed widespread disappointment and resentment, Second City became a high-stakes place where the right nod could propel you to your own late-night show, or a lucrative writer’s room, or a spot in the “Saturday Light Live” cast. Through no fault of their own, producers (and, in full disclosure, critics) came to be perceived as gatekeepers in a zero-sum game. That change was, in many ways, a tribute to the formative re-invention of American comedy that the brilliant Fey, Colbert and their friends worked out during their eight shows a week, a progressive aesthetic that now dominates late-night television. But it also was indicative of an environment infused with, yes, white privilege.

Many at Second City were slow to see that danger, especially since the death of the nurturing, big-hearted producer Joyce Sloane had meant that the performers, especially those of color, were left dangling in front of audiences who were coarsening along with the rest of America. Great sketch comedy requires profound personal vulnerability. I, for one, was too slow to see how much that cost some of those performers.

Compared to its peers, Second City was relatively early to diversify its casts. But it did not offer sufficient support backstage to allow artists of color to dedicate themselves to the demands of an art form inherently rooted in dealing with anything and everything in the moment.

And the moment had changed. Civility was decreasing. Overt racism from a minority of the audience had been emboldened. The list of things that were funny to all was growing ever shorter. The willingness to poke fun at your own political side was evaporating. The libertarian center upon which American satire had depended was not holding. Second City ruptured in large part because America ruptured first.

So what happens next? Who will buy Second City?

Perhaps a massive media company looking for a talent pipeline (they do, after all, run the entertainment world). That would make sense, although control might pass away from Chicago and the product may grow more bland. Maybe some of the activists will find the funding and build a more radical and anti-capitalist Second City on the vanguard of new revolutionary change. That would be interesting. If it is true to itself and can find an audience.

Second City does not own its own building. Ownership of the theater has come to mean trying to pay the rent.

That will end. Whatever happens, I hope for an owner as invested in Chicago as the industry and who understands how this troubled but beautiful city is inextricably linked with this one place to go, where you used to be able to laugh at everything.

Chris Jones is a Tribune critic. He can be reached at [email protected]

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