Brian Posen Details the History of the Chicago Comedy Scene

Brian Posen
4 min readDec 4, 2019
Brian Posen Details the History of the Chicago Comedy Scene

There are only a few things synonymous with Chicago. Deep dish pizza, the Sears Tower, the Chicago Cubs, and last, but certainly not least, comedy. The Windy City has been home to a thriving comedy scene for decades. It is where some of the biggest comedians in history have come through on their way to super stardom. But like everything, Chicago’s comedy scene has undergone change over the years. Brian Posen is one person who can speak to this evolution. Posen is an accomplished actor, director, and producer who has dedicated his career to the theater scene in his native Chicago. He taught for 25 years at the renowned comedy theater The Second City, before going on to found and serve as creative director for Stage 773. In addition to his programming responsibilities, Chicago’s Brian Posen coach’s ensemble performances weekly and has been an integral part of thousands of sold-out shows. In essence, no one knows Chicago’s comedy scene better than Brian Posen.

Chicago Comedy of the Past and Present

Comedy in Chicago began as early as 1955, when modern improv was born at the University of Chicago. A group of students formed a troupe called the Compass Players, which by 1959, had morphed into what we know today as The Second City. In addition to shows, workshops and classes were taught here. The Second City quickly grew in popularity, in part thanks to the number of comedians who performed there and went on to become some of the most famous comedians of the 1970s, 80s, and 90s. The iO was the next comedy club to open in Chicago, and it was founded by Del Close, a core member of The Second City. These two clubs dominated the city and put Chicago on the map as the place to be for comedians.

So, what’s changed? Although Chicago is still synonymous with comedy, today there is more competition than ever before. This relates not only to the sheer number of aspiring comedians that are flocking to the city, but also to the number of comedy theaters and shows popping up. Brian Posen asserts that while Second City used to be the club in Chicago, many others have entered the mainstream in recent years, such as The Annoyance or Stage 773, to the point that you’re just as likely to “make it” by performing at any one of them. Some of these clubs have only been founded in the last decade, while the perception around others has shifted. Take the iO Theater, for example. This theater has been around for a long time; however, it was initially perceived as the place to go to test out improv ideas that actors would then take over and perform at The Second City. In the present day, the iO theatre is seen as the destination, not just part of the journey, with actors vying to perform there. In addition to the primary theaters, there are also a variety of short run shows such as the Chicago Women’s Funny Festival and the Wait Wait…Don’t Tell Me radio that are only in town for part of the year.

One thing’s for sure, Chicago continues to remain the best place in America for comedy.

Top Comedy Clubs in Chicago

1. The Second City. To this day, The Second City remains one of the top comedy clubs in all of Chi-Town. Not only does The Second City specialize in both improv and sketch comedy, but it has launched the careers of many of the biggest comedians in history. The Second City is responsible for Tina Fey, Stephen Colbert, Bill Murray, and Steve Carell, to name a few.

2. Zanies. One of the great examples of old time comedy in Chicago, Zanies still holds onto the ideals of old. Offering stage time to the up-and-comers in the Chicago scene, as well as honoring the all-time greats, Zanies offers a perfect blend of traditional and contemporary comedy.

3. The Annoyance Theatre & Bar. Like The Second City, The Annoyance Theater & Bar is one of the longest running comedy clubs in Chicago. In 2014, it moved locations and is now in a building with two theatres. According to Brian Posen, the Annoyance has all types of comedy from sketch to stand-up, as well as a bar where you can sit and relax post-show.

4. iO Theater. One of the most well known and successful clubs in Chicago, the iO theater has consistently produced some of the top comedy talent, not only in Chicago but in the country. With names such as Seth Meyers and Amy Poehler, the iO theater highlights long-form improve and a variety of classes for those who wish to learn or improve.

5. The Playground Theater. According to Brian Posen, The Playground Theater has earned a reputation for being the only comedy club in Chicago dedicated to the art of improvisation. It is a non-profit theater with an undeniable energy thanks to the young, often college-age students that perform here.

6. Stage 773. Stage 773 on Chicago’s Belmont Avenue is a large venue with multiple stages for comedy. It has hosted an array of top-notch comedy shows, including the Chicago Women’s Funny Festival, and is even responsible for one of the city’s largest sketch comedy festivals each year.

7. CSz Theater. Located in the heart of the Windy City’s Lakeview neighborhood, the CSz Theater hosts their titular ComedySportz show every Thursday, Friday, and Saturday evenings. Opening in 1987, the CSz Theater has been a staple of the Chicago scene from its beginnings.

8. The Neo-Futurists. The Neo-Futurists club takes many of the ideas of a comedy theater and turns them on its head. With ticket prices being based on a dice roll, the Neo-Futurists club is an unrated club that believes that art should be without censorship and promotes the ideals of free speech.

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Brian Posen

An accomplished actor, director, and producer, Brian Posen has dedicated his career to the theater scene in his native Chicago.