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Panel: The History of Chicago Comedy

March 27, 2022 @ 1:00 PM 2:00 PM CDT

Chicago has stood at the center of modern comedy since the mid-1950’s as mother-in-law jokes were being set aside for the cutting edge stand-up and the emergence of improv-based sketch comedy. Longtime Second City creative executives Anne Libera and Kelly Leonard will be co-moderators of a panel that will share rich insights and stories of such Chicago comedy icons as Bob Newhart, Bernie Mac, Bill Murray, Joan Rivers, Tina Fey, Stephen Colbert, and more.

This event will be livestreamed! Use the button on the right on the day and time of the event.

Panelists: Jennifer Estlin, Rick Kogan, Raymond Lambert, and Mick Napier.


Anne Libera is director of comedy studies and oversees the BA in Comedy Writing and Performance at Columbia College Chicago, a collaboration with The Second City. She was previously executive artistic director of The Second City Training Centers, where she created its youth program, summer camps, and directing and musical improv programs. Her directing credits include Stephen Colbert’s one-man show Describing a CircleThe Madness of Curious George, and Computer Chips and Salsa. Libera authored The Second City Almanac of Improvisation, guest lectured at Stanford Business School, and was an artistic advisor to the Museum of Science and Industry. She serves on the governing board for Gilda’s Club Chicago.

Kelly Leonard is the Executive Director of Insights and Applied Improvisation at Second City Works, overseeing The Second Science Project with the Center for Decision Research at the University of Chicago’s Booth School of Business. His book, “Yes, And,” was published to critical acclaim by HarperCollins. Kelly has spoken at Aspen Ideas Festival, Microsoft and TEDxBroadway and hosts the podcast “Getting to Yes, And” for WGN and Second City. For over twenty years, he oversaw Second City’s live theatrical divisions working with such talent as Tina Fey, Stephen Colbert, Amy Poehler, Seth Meyers, Keegan Michael Key and others.


Jennifer Estlin has been an accomplished actor, and is also President and Executive Producer of Annoyance Productions since 2001. She has appeared in many Annoyance shows, most recently, 40 Whacks, Tommy’s Place, Late Night Tit-Bits, and The Invention Show. Her television/film credits include Answer, Now, Choose, Law and Order (Cathy Briscoe), Late Nite with Conan O’Brien, Volcano, iMurders, The Stand-In, and Chicago Boricua (directed by Annoyance alum Marisol Torres). Jennifer is also an alum of The Second City, where she performed on the Northwest and Flamingo-Las Vegas stages, as well as in the National Touring Company. She is a graduate of Northwestern University.

Rick Kogan began his career at sixteen, working for the Chicago Sun-Times during the tumultuous Democratic Convention of 1968. He is currently senior staff writer and columnist for the Chicago Tribune Sunday Magazine and host of the popular WGN-AM Sunday Papers radio program, which airs in thirty-eight states and Canada. He was named Chicago’s Best Reporter in 1999, Chicago’s Greatest Living Journalist in 2002, and was inducted into the Chicago Journalism Hall of Fame in March 2003. A longtime friend to Ann Landers and her editor for the last five years of her life, Kogan lives with his wife in Chicago.

Raymond Lambert is an entrepreneur, independent producer, and adjunct professor at Columbia College. He wrote and produced the award-winning documentary film Phunny Business, and is executive producer on “Maya Angelou: The Peoples Poet.” He is the founder of the comedy club All Jokes Aside.

Mick Napier is Founder and Artistic Director of the acclaimed Annoyance Theatre and a director and artistic consultant for The Second City. His work has included the Jeff Award winning Paradigm Lost and Obie award winning One Woman Shoe. As an actor, Mick has appeared in Ice Harvest, Let’s Go to Prison, Watch, Talent, and on the Canadian reality show Next Comedy Legend. Mick’s book, Improvise: Scene from the Inside Out is widely regarded as a seminal work on the subject of improvisation.

This panel will be 60 minutes in length plus an additional 15 minutes of Q&A (75 minutes total). This panel will be free to attend, but you must register for a ticket.

851 W Belmont Ave
Chicago, IL 60657 United States
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(773) 697-9693
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