Second City’s Anne Libera writes the playbook on being ‘Funnier’

Second City’s funny girl, Anne Libera, has spent decades shaping the way Chicago, and the world, understands comedy. Now, the longtime Second City director and educator is bringing her experience to the page with the upcoming release of her newest book, Funnier: A New Theory for the Practice of Comedy.

A familiar name to anyone who has come through Second City’s storied stages, Libera has worn many hats in Chicago’s comedy scene. She began her journey at The Second City in the 1980s, directing shows that spotlighted the sharp wit and physical play of performers who would continue on to national acclaim. From Stephen Colbert’s one-man show Describing a Circle to touring productions across the U.S. and Europe, her directorial fingerprints are on some of the company’s most memorable work.

Beyond the stage, Libera served as Executive Artistic Director of Second City Training Centers and Education Programs from 2001 to 2009, and today she is Director of Comedy Studies at Second City as well as Associate Professor at Columbia College Chicago. There, she helped launch the ‘Comedy Writing and Performance B.A. degree’, the first of its kind, creating a formal academic home for the study of comedy. Her students have included Amy Poehler, Jordan Peele, Kristen Schaal, Steven Yeun, and Ashley Nicole Black, among many others.

Anne Libera Funnier

Her new book Funnier: A New Theory for the Practice of Comedy distills those decades of experience into a framework for anyone serious about the craft of comedy. At 352 pages, the book breaks down what often seems like comic instinct into a set of practical tools, from writing and revising jokes to building characters and shaping narratives, and the significance of comedy’s ethical responsibilities. With a foreword by Ashley Nicole Black, Chelsea Devantez, Ariel Dumas, and Jenny Hagel, Funnier makes the case that being funny isn’t an inborn talent, it’s a skill that can be taught, practiced, and honed.

Libera has always been at the intersection of art and education. In addition to teaching and directing, she has collaborated with behavioral scientists through The Second Science Project, presented at the Aspen Ideas Festival and Code Conference, and guest lectured at Stanford Business School. Her earlier book, The Second City Almanac of Improvisation, is already a staple for improv students and teachers. This latest offering will surely join those ranks.

Funnier, adds another chapter, in Libera’s own career and for the comedy community in Chicago and beyond. For an industry that thrives on instinct, collaboration, and craft, Libera’s work promises to give comedians, writers, and educators new ways to think about the practice of making people laugh.

In its final section, Libera reflects on her own experiences, stressing that comedy is not only about getting laughs but also about considering the impact of those laughs. She urges future writers to think about the ethics of their craft and the responsibility they hold toward their audiences. The takeaway is clear: this book won’t just help readers be funnier, it will help them be better people.

Funnier: A New Theory for the Practice of Comedy will be published in October 2025 by Northwestern University Press.


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