The Chicago Comedy Scene: How One City Became American Comedy's Training Ground

So much American comedy comes out of Chicago because the city turned improvisation into a profession. The Compass Players (1955) and The Second City (1959) invented improv as a theatre form, Del Close and Charna Halpern's ImprovOlympic turned long-form improv into an art in the 1980s, and a dense network of schools, cheap stages and TV scouts did the rest. Alongside the improv empire, Chicago also grew a scrappy alternative stand-up scene that produced Hannibal Buress, Kumail Nanjiani and Sarah Sherman.

This guide traces the whole lineage, from university-town experiment to the post-pandemic scene. For the New York institution that Chicago's improvisers founded, read our history of the UCB Theatre.

The Compass Players (1955–1958)

Chicago comedy starts with a group of University of Chicago people who wanted theatre for ordinary audiences. David Shepherd and Paul Sills founded the Compass Players in 1955 in Hyde Park. Performers improvised scenes from outlines and audience suggestions, building on the theatre games developed by Sills' mother, Viola Spolin, whose book Improvisation for the Theater (1963) became the foundational text of American improv teaching.

The Compass was short-lived but astonishing. Mike Nichols and Elaine May met there and built the double act that made them stars. Del Close, who would shape the next half-century of improv, joined a later version of the company. It was the first time anyone had made a working theatre out of improvised comedy.

The Second City (1959 onward)

Sills, Bernard Sahlins and Howard Alk opened The Second City in December 1959. The name came from a dismissive New Yorker series about Chicago. The format it settled on has barely changed: a revue of sketches developed through improvisation in rehearsal, followed by an improvised set where new material is tested on the audience. The improvisation is the writing process; the finished show is mostly scripted.

The alumni list is the history of American comedy. The early casts included Alan Arkin and Barbara Harris; later decades brought John Belushi, Bill Murray, Harold Ramis, Shelley Long, George Wendt, Chris Farley, Tim Meadows, Stephen Colbert, Steve Carell, Tina Fey, Rachel Dratch, Keegan-Michael Key, Jason Sudeikis, Cecily Strong, Aidy Bryant and Tim Robinson, whose I Think You Should Leave is in some ways the strangest possible descendant of the Second City sketch.

A Toronto company opened in 1973 and produced SCTV (1976–1984), with John Candy, Catherine O'Hara, Eugene Levy, Martin Short, Andrea Martin, Rick Moranis and Dave Thomas. For decades Second City was a direct feeder to Saturday Night Live, beginning with Belushi, Gilda Radner and Dan Aykroyd in the first cast.

Second City also became a business: a large training centre, touring companies, corporate workshops and outposts in other cities. In 2020 its longtime owner Andrew Alexander stepped down amid criticism from Black alumni about how the theatre treated performers of colour, and in 2021 the company was sold to a private equity firm.

Del Close and iO: the long-form revolution

The single most important figure in Chicago improv is Del Close (1934–1999): actor, Second City director, teacher and a famously chaotic personality. Close believed improvisation could be the finished art rather than a writing tool. With Charna Halpern, who founded ImprovOlympic in 1981, he developed that belief into a method from 1983 onward.

The centrepiece was the Harold: a roughly half-hour improvised piece in which a team takes one suggestion, explores it in an opening, then weaves three separate scene threads through several rounds, broken up by group games, until the threads connect. It is to a sketch what a novel is to a short story. Close, Halpern and Kim "Howard" Johnson set out the philosophy in Truth in Comedy (1994), still one of the standard improv books.

The 1980s and 1990s iO generation is remarkable. Students and performers there included Chris Farley, Mike Myers, Tina Fey, Amy Poehler, Adam McKay, Horatio Sanz, Matt Besser, Ian Roberts and Matt Walsh. When the last four opened the UCB Theatre in New York in 1999, they took the Harold with them, and through UCB it became the default long-form structure in American improv.

Close died in March 1999. (He famously left his skull to the Goodman Theatre so he could keep acting.) ImprovOlympic shortened its name to iO in the early 2000s and moved to a large complex on North Kingsbury Street in 2014. It closed in June 2020: Halpern cited pandemic losses and a large tax bill, while the theatre was also facing a petition about racism. New owners reopened it in November 2022.

The Annoyance and the outsiders

Not everyone wanted the Second City revue or the iO Harold. In 1987 Mick Napier and friends started a company called Metraform, which became the Annoyance Theatre in 1989. Its sensibility was deliberately trashier, more theatrical and more willing to fail. Its biggest hit was the improvised-then-set musical Co-Ed Prison Sluts, which ran from 1989 to 2000 and is often described as the longest-running musical in Chicago history. The Real Live Brady Bunch, which restaged sitcom episodes word for word, started there and featured Jane Lynch.

Napier's book Improvise: Scene from the Inside Out (2004) argued against rule-heavy improv in favour of making strong choices and committing. Along with Susan Messing and other Annoyance teachers, he gave the city a counter-tradition that prized character and nerve over structure.

Further out still, the Neo-Futurists ran Too Much Light Makes the Baby Go Blind, attempting thirty short plays in sixty minutes, from 1988 to 2016, and continue with a successor show. It isn't comedy in the club sense, but it belongs to the same Chicago habit of treating rapid, audience-facing performance as an art form.

The Chicago stand-up scene

Chicago's stand-up tradition is quieter than its improv empire, but it has produced a distinctive kind of comic: unhurried, odd, often very dry. Mainstream clubs such as Zanies (opened 1978) anchored the circuit, while the alternative scene grew in bars and back rooms.

• The Lincoln Lodge began around the turn of the millennium in the back room of the Lincoln Restaurant on Lincoln Avenue, a showcase with a variety-show format and rotating hosts. It now runs from its own space in Logan Square and bills itself as one of the country's longest-running independent comedy showcases.
• Chicago Underground Comedy, a weekly show at the Beat Kitchen, became a key room for the 2000s generation.
• Open mics in bars across the North Side gave comics far more stage time than New York or LA could offer a beginner, at a fraction of the rent.

The comics who came up in that scene in the 2000s include Hannibal Buress, Kumail Nanjiani, Pete Holmes, Kyle Kinane, Cameron Esposito and Beth Stelling. Most of them eventually left for New York or Los Angeles, which is the pattern: Chicago develops, the coasts employ.

In the 2010s a stranger DIY layer emerged in bars, galleries and basements. Sarah Sherman developed her body-horror, multimedia act there, including the show Helltrap Nightmare, before moving to New York and joining SNL in 2021. It is a good example of how Chicago's cheapness lets performers build something weird for years before anyone in the industry sees it.

How a Chicago comedy career works

The classic Chicago path is slow and structured, unlike the "get seen in a showcase" model of New York:

1. Move to the city in your twenties and take classes at Second City, iO or the Annoyance, often more than one.
2. Perform constantly on indie teams, house teams and late-night shows, mostly unpaid.
3. Audition for Second City's touring company, then its smaller stage, then the mainstage, where performers are paid and scouted.
4. Get hired by SNL or a TV writers' room, or move to the coasts and start again.

That apprenticeship can take most of a decade. It produces performers who are extremely good at ensemble work and character, which is why Chicago alumni dominate sketch television. It is also slow, expensive in class fees, and for many years it was hard for performers who didn't fit the scene's mostly white, mostly male norms. Those criticisms came to a head in 2020 at both Second City and iO.

The scene today

As of 2026, the big three institutions are all operating: Second City under its newer ownership, iO since its 2022 reopening, and the Annoyance on Belmont Avenue. The pandemic thinned the field of smaller theatres, and the decline of the UCB model in New York has made Chicago's apprenticeship look more distinctive again. The stand-up and DIY scenes remain lively, with showcases, mics and odd one-off shows in bars, breweries and galleries (the same trend we cover in the rise of micro-venues).

For a deeper look at the form itself, see our guide to improv and alternative comedy, and for one of the most successful Chicago-to-LA careers, our profile of Bob Odenkirk, who wrote and performed at Second City before Mr. Show.

Frequently asked questions

Why does so much comedy come out of Chicago?

Chicago invented improvisational theatre as a professional form (the Compass Players in 1955, Second City in 1959) and built schools around it. Rents were lower than New York or LA, stage time was plentiful, and SNL and TV producers scouted there for decades.

When was iO (ImprovOlympic) founded?

Charna Halpern founded ImprovOlympic in Chicago in 1981, and Del Close began teaching there in 1983. It shortened its name to iO in the early 2000s, closed during the pandemic in 2020 and reopened under new owners in November 2022.

Who was Del Close?

Del Close (1934–1999) was an improviser, director and teacher who developed the Harold, the long-form improv structure taught at iO and later UCB. His students included Chris Farley, Mike Myers, Tina Fey, Amy Poehler and the founders of the Upright Citizens Brigade.

What is the difference between Second City and iO?

Second City produces sketch revues written from improvisation, performed by paid casts. iO was built around long-form improvisation itself, especially the Harold, performed by house teams as the finished show.

Did Sarah Sherman start in Chicago?

Yes. Sarah Sherman developed her gross-out, multimedia style in Chicago's DIY comedy scene in the 2010s, including her show Helltrap Nightmare, before moving to New York and joining Saturday Night Live in 2021.