Don’t Forget to Laugh: Chicago’s Funniest People Part 3

Today we continue our list of Chicago’s funniest people because, well, does any city breed more comedic talent per square foot? There isn’t a list long enough to shine a spotlight on all of the Windy City’s great comedians, but we hope that you have found some new comics to check out or rediscover some old favorites to provide much-needed laughs during the COVID-19 pandemic. Wherever your tastes may lie when it comes to humor, our city historically produces funny folks spanning the spectrum of hilarity. So let’s look at the comedians who got their start in Chicago before moving on to become titans in pop culture.

Keegan Michael-Key: The Key and Peele star followed in the footsteps of so many other comedy greats by honing his skills at Second City after arriving in the city in 2001. The hysterical performer won two Jeff Awards while at Second City for his work in Curious George Goes to War and Holy War, Batman! Or the Yellow Cab of Courage. Key moved on to become a cast member on MADtv, where a wider audience was exposed to his gift for creating unique characters and spot-on impressions.  The comedian’s success skyrocketed when he joined forces with Jordan Peele to create the groundbreaking sketch show, Key &Peele. The duo’s work together has earned them Peabody and Emmy awards as well as millions of hits on YouTube for their fresh and hysterical sketches.

Tina Fey: Upon arriving in Chicago in 1992, Fey began taking classes at, where else, Second City. It didn’t take long for the funny woman to become a featured player at the Chicago comedy club. From the improv stages of Second City, Fey segued to a writing gig at Saturday Night Live, where she eventually became SNL’s first female head writer and a featured performer. Her work on the Weekend Update sketches alongside Jimmy Fallon, and then Amy Poehler cemented Fey as one of the best to perform the SNL mainstay. Tina Fey left SNL and created, wrote, and starred in the beloved sitcom 30 Rock, which ran from 2006 to 2013, which won her Emmy, Screen Guild, and Golden Globe awards for Best Actress in Comedy Series. Not too bad for a comic who got her start while living in Rogers Park.

Joan Rivers: Without a doubt, Joan Rivers is one of the funniest human beings to ever stand on a stage. Although her career started in New York City and she had some movie roles under her belt, Rivers came to Second City in 1961 and really sharpened her comedic chops. While her stay in the city didn’t last very long, Rivers indeed developed the unmistakable razor-sharp aggressive wit that catapulted her to fame in the ensuing decades. From appearing on The Ed Sullivan Show and The Carol Burnett Show to becoming the first female host of a major network late-night talk show and her legendary red carpet work with her daughter, Melissa, Rivers was genuine comedic gold. Upon her death in 2014, Rivers was undoubtedly responsible for opening doors for female comedians, and the city of Chicago played a role in shaping the legend’s unmistakable style.

That does it for our list of amazing funny people that got their start while hitting the comedy stages of Chicago. This list is by no means complete as there simply aren’t enough blog posts to cover the incredible amount of comics that have called Chicago home at one point or another. Sure, New York City gets the glitz and glamor, and California has all the pretty people, but when it comes to humor, Chicago has always held a tight grip on the nation’s funny bone.

ERIC KAPLAN AND DEAN’S TEAM CHICAGO