Sixty-five years of launching comedy legends, and a front-row seat to the 114th Mainstage Revue, Pandemonium, Please Hold
After spending part of the trip at Billy Goat Tavern, retracing the steps of the SNL cast that made it famous, it felt only right to follow that thread back to where so many of those careers actually began. The Second City, tucked into Old Town, isn’t simply a comedy club. It’s the institution most responsible for shaping modern American sketch comedy, and an evening there made for one of the most fun nights of the entire trip.
From University of Chicago Intellectuals to a Comedy Empire
The theater opened on a snowy Chicago night in December of 1959, founded by Bernie Sahlins, Howard Alk, and Paul Sills, the son of improv pioneer Viola Spolin. Its name was actually meant as an insult: a New Yorker writer had dismissively referred to Chicago as merely “the second city” in comparison to New York, and the founders, with characteristic comedic defiance, simply adopted the slight as their name. Built directly on Spolin’s groundbreaking improvisational games and techniques, the small cabaret theater grew, over the following decades, into what’s widely considered the most influential comedy training ground in the world.
The roll call of alumni who passed through its stage reads like a history of American comedy itself: John Belushi, Bill Murray, Gilda Radner, and Dan Aykroyd in the 1970s; Mike Myers, Chris Farley, and Bonnie Hunt in the decades that followed; Tina Fey, Steve Carell, and Stephen Colbert more recently still. Belushi, fittingly enough, made his Second City debut in 1971, the same era he’d later help turn Billy Goat Tavern into a household name on Saturday Night Live just a few years later. When SNL premiered in 1975 with a cast built substantially from Second City’s ranks, the theater effectively became the show’s unofficial farm system — a pipeline that, fifty years on, is still running.
Pandemonium, Please Hold
The show we caught, Pandemonium, Please Hold, is the theater’s 114th Mainstage Revue — a number that alone tells you something about the company’s sheer staying power. Performed by a six-person ensemble, the revue moves at a relentless clip through scripted sketch comedy, audience-driven improv, and full musical numbers, all built around the very of-the-moment premise that everyday life has started to feel like chaos, and that laughing at it together is one of the few reliable antidotes left. True to Second City’s improvisational roots, the cast pulls real audience suggestions into the show, which means no two performances run quite the same way twice.
What struck us most was how tightly constructed the chaos actually was. Behind the loud, fast, deliberately unhinged energy on stage is a genuinely disciplined writers’ room process, workshopping and cutting material in rehearsal until only the sharpest bits survive — we later read that even a sketch built around Chicago’s beloved late-night Tamale Guy didn’t make the final cut, despite the obvious local appeal, simply because it didn’t land. That kind of relentless editing is exactly why the surviving material hits as hard as it does.
A Night Worth Building an Evening Around
The Old Town setting itself adds to the appeal — an intimate, unfussy room that puts you close enough to the stage to feel genuinely part of the show rather than simply watching it. Tickets start affordably and the show runs Tuesday through Sunday, making it an easy addition to an evening that might also include dinner nearby beforehand. It’s the kind of night that rewards going in with low expectations and almost no information about what’s coming, since half the fun is simply not knowing where the cast will take a scene next.
A Night We Both Enjoyed
This was one of those Chicago evenings that reminded us why we like traveling together. The Second City might have been more firmly on Paul’s radar than mine, but by the time the curtain came down, I was laughing as much as he was.
There’s something particularly enjoyable about seeing a partner light up over an experience they were genuinely excited about—and discovering that their enthusiasm was contagious.
Why It Belongs on the List
The Second City has spent sixty-five years proving that Chicago, far from being anyone’s second choice, is the city that actually taught America how to be funny. Pandemonium, Please Hold carries that legacy forward with real confidence — sharp, current, and genuinely, consistently funny from start to finish. If your Chicago itinerary has room for one night of pure entertainment, this is the one to book.
For the rest of where we stayed, ate, and explored on this trip, look for the complete Chicago guide coming soon to The Insider’s Guide. In the meantime, stay tuned for the next blog post in this Chicago series.
