When audiences arrive at Chicago’s renowned Second City comedy theater, their comedy experience starts before the show even begins.  Lining up inside the theater hallway waiting for the show to start, they are surrounded by photos of famous alumni such as Dan Aykroyd, John Belushi, Bill Murray, Stephen Colbert and Tina Fey.  Second City creates this line intentionally because it primes audiences to be in the right frame of mind to laugh once the performers hit the stage.  Second City has plenty of photos to hang on the walls because it has been putting on sketch comedy and improv shows successfully for over five decades.  It also trains thousands of students to become comic actors, writers and directors.  Second City describes itself as both a laboratory of comedy and a professional comedy theater.

With all those years of experience, Second City has developed strong views of why and how its favorite philosophies of funny create excellent results inside rehearsals and writing rooms; on stage; and inside businesses.  As part of its offerings, Second City goes to companies in person to work with employees, and it also creates humor products, such as funny training videos for businesses.

To get the skinny on Second City, we spoke with two long-time Second City executives and creatives: Producer Kelly Leonard and Director and Teacher Anne Libera.  Libera also teaches the first BA program on Comedy Studies in the United States at Columbia College.

When you meet Kelly Leonard, it’s obvious that he is quick to make a joke.  In fact, a joke may be the first words you hear from him.  That’s because the second he walks in the door he finds something funny about the encounter he is about to have.  In the context of a meeting where he is the guest, he might enter and notice that everyone is wearing a suit except for him and make a joke about that.  Or perhaps he finds humor in the fact that a room is too small for the meeting and makes a joke about not stepping on toes:

Or, if he is the keynote speaker before drinks at a conference, he might quip: “I understand that I am the thing standing between you and the free alcohol, so I will not go long.”

Leonard is also more than eager to be the butt of the joke.  In fact, he notes that Anne Libera (also his wife) constantly pokes fun at him when they are presenting in all sorts of contexts.  He says the idea of being fine with being the butt of the joke makes everyone more appealing.

Another part of Leonard’s humor style is that he likes to keep it smart.  He says when you work in a historic venue like Second City, with its particular brand of humor, it comes with the expectation that you are playing at the top of your intelligence.  A dumb joke isn’t out of the question, but you better be sure that that dumb joke is the smartest dumb joke you could possibly make.

For Anne Libera, finding her unique sense of humor was a journey.  She says that for a long time she didn’t consider herself funny, although she was very good at the technical parts of helping other people be funny.  However, she discovered over time that hanging out with funny people began rubbing off on her.  More than that, she discovered a key lesson for being funny in a variety of situations:

For example, she found that people laughed when she talked about her obsession with middle grade children’s literature.  Or when she detailed what runs through her head when she knows she is going to be late picking her children up from daycare:

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