Jonathan Pitts

Jonathan Pitts is a Chicago-based improv theatre artist, producer, and educator who has shaped the institutional infrastructure of American improv for more than three decades. As co-founder and producer of the Chicago Improv Festival for twenty years, creator of the College Improv Tournament, founder of the Teen Comedy Fest, and a sixteen-year faculty member at The Second City Training Center, Pitts has operated simultaneously as a performer, teacher, and institution builder. He trained under Paul Sills, Byrne Piven, David Shepherd, Sheldon Patinkin, and Del Close, connecting his practice directly to the foundational generation of American improv. His Global Improv Walkabout project has taken him to twenty-eight countries and more than one hundred fifteen cities, making him one of the most widely traveled improv practitioners in the world.

Pitts began performing improv in Chicago in the late 1980s, studying under a lineage of teachers that included Paul Sills, Byrne Piven, David Shepherd, Sheldon Patinkin, Alan Baranowski, and Del Close. This direct exposure to the first and second generation of American improv founders gave his practice a historical grounding that informed both his performance work and his later institution-building.

He joined The Second City Training Center as a teacher, coach, and director, serving on faculty for sixteen years. During this period he contributed as a writer to Anne Libera's The Second City Improv Almanac, documenting the pedagogical approach he had absorbed from his own teachers. He was selected by New City magazine as one of Chicago's Top 50 Theatre Players for three consecutive years.

Pitts co-founded the Chicago Improv Festival and served as its producer for twenty years, building it into one of the major annual gatherings of the American improv community. He simultaneously served as Executive Director of Chicago Improv Productions, the producing organization behind the festival and related programming. He created and produced the College Improv Tournament for ten years, providing a competitive platform for collegiate improv teams. He founded and produced the Teen Comedy Fest for seven years, extending structured performance opportunities to high school improvisers. He later founded and produced the Chicago Podcast Festival.

As a creator and director, Pitts developed original improv formats including The Oracle, The Silent Movie, Storybox Unscripted Theatre, The Make 'Em Ups, Double Play, Frames, Lucky Red Dragon Karaoke Night, Maxwell Street, Solo Plus One, Stopwatch, Storybox For Kids, and Viola Spolin: Woman of Play. The range of these formats reflects his interest in expanding the formal vocabulary of improv beyond Harold-derived long-form structures.

Pitts teaches at Piven Theatre Workshop in Evanston, the acting school co-founded by Byrne and Joyce Piven that emphasizes story theatre and Viola Spolin's theater games. His Global Improv Walkabout project has taken him to twenty-eight countries and over one hundred fifteen cities to perform and teach, using improv as a tool for cross-cultural connection. He continues to guest-instruct at international festivals, including the Auckland Improv Festival in 2026.

Historical Context

Pitts emerged from a Chicago improv ecosystem in which the founding generation was still actively teaching. His direct study under Paul Sills, the inventor of theater games as a performance form and son of Viola Spolin, and under Del Close, the developer of the Harold and the philosophical architect of long-form improv, placed him at the intersection of two parallel traditions: the Spolin/Sills game-centered approach and the Close/Halpern long-form approach. Few practitioners of his generation received sustained instruction from both lineages.

The Chicago Improv Festival that Pitts co-founded and produced for two decades became one of the primary gathering points for the national improv community, bringing together performers and teachers from across institutional boundaries. At a time when Chicago's improv landscape was defined by institutional rivalries between The Second City, iO, and the Annoyance, the festival provided a neutral platform where practitioners from competing schools could share stages and exchange methods.

Pitts's departure from the Chicago Improv Festival in 2017 marked a generational transition in Chicago's festival landscape, as the event had run continuously under his leadership since its founding. His subsequent focus on the Global Improv Walkabout reflected a shift from domestic institution-building to international outreach, carrying Chicago-rooted techniques to improv communities in Asia, Africa, Latin America, Europe, and Oceania that had limited exposure to the Spolin/Close tradition.

Teaching Philosophy

Pitts's teaching integrates the game-centered approach of Viola Spolin, which he absorbed through study with Paul Sills and Byrne Piven, with the scenic and narrative principles he developed at The Second City. His workshops emphasize improvisation as a tool for connection across cultural and linguistic barriers, a principle tested through his work in twenty-eight countries where shared stage language must transcend spoken language differences. Students consistently describe his teaching as addressing both improv fundamentals and broader applications of the skills to personal and professional contexts.

Legacy

Pitts's twenty-year stewardship of the Chicago Improv Festival established one of the longest-running institutional platforms for the American improv community. The festival's neutral positioning across Chicago's competitive institutional landscape provided a model for how improv organizations could collaborate rather than compete, anticipating the cross-institutional exchange that later became standard at festivals worldwide.

His creation of the College Improv Tournament and Teen Comedy Fest extended structured performance opportunities to younger improvisers at a time when most festivals and training programs were oriented toward adults. These programs helped formalize a pipeline from educational improv to professional training centers, connecting high school and college performers to the Chicago institutional ecosystem.

The Global Improv Walkabout represents an ongoing effort to decentralize improv's geographic concentration in a handful of American and European cities. By carrying Chicago-rooted techniques to communities in countries without established improv traditions, Pitts functions as a direct transmission link between the founding generation of American improv and emerging scenes across the global South and East.