Brian Stack
Brian Stack is a comedy writer and performer from the Chicago improv tradition, best known as a staff writer and on-air character performer for Late Night with Conan O'Brien and the subsequent Conan programs across eighteen years. A product of iO Chicago's Harold era under Del Close and Charna Halpern, he performed on landmark ensembles including Jazz Freddy, Blue Velveeta, and Bouquet of Flesh before joining the Second City touring company and eventually transitioning to network television. He received five Writers Guild Awards and an Emmy Award during his television career, and joined The Late Show with Stephen Colbert as a writer in 2015. He has continued to perform monthly at UCB's Gravid Water show in New York.
Career
Brian Stack was born on August 18, 1964, in Park Ridge, Illinois, and grew up in Palatine. He studied telecommunications at Indiana University, graduating with Phi Beta Kappa honors in 1986; it was there that he first encountered Mick Napier in an acting class, a connection that would shape his subsequent trajectory in Chicago performance. Stack continued his education at the University of Wisconsin-Madison, earning a Master of Arts in Communication Arts in 1988, during which time he performed with the Ark Improvisational Theatre, a Madison ensemble whose members during this period included Chris Farley and Todd Hanson, who later became a founding writer at The Onion.
After graduate school, Stack relocated to Chicago and spent approximately four years working in advertising, continuing to pursue performance in the city's growing improv community during evenings and weekends. By the early 1990s he had established himself within the ImprovOlympic, the ensemble long-form theater founded by Charna Halpern and directed artistically by Del Close, who had codified the Harold as the foundational long-form structure for American improv. Stack performed on several notable ImprovOlympic ensembles during this period, including Bouquet of Flesh; Blue Velveeta, which included Andy Richter, Dave Koechner, and Susan Messing among its members; Jazz Freddy; and Gambrinus King of Beer. His primary mentors at the ImprovOlympic were Del Close, Charna Halpern, and Dave Pasquesi. It was during Jazz Freddy that he met the actress and improviser Miriam Tolan, whom he would marry on June 1, 1996.
Stack joined Second City's GreenCo touring company approximately in 1992, a company whose membership during his tenure included Pat Finn, Adam McKay, Rachel Dratch, and Amy Poehler, performers who would later figure prominently in American comedy. He remained with the touring company through approximately 1996, developing the sketch-writing and character-performance skills that would define his subsequent television work.
In 1997, Stack joined Late Night with Conan O'Brien on NBC as a staff writer, initially hired for a thirteen-week contract engagement that became a permanent position. His first sketch on the program paired him with Amy Poehler in the piece 'Andy's Little Sister, Stacy.' He developed a sustained presence as an on-air character performer alongside his writing work, appearing in recurring roles that included Frankenstein, The Interrupter, and Ghost Crooner, among others. Stack followed O'Brien to The Tonight Show on NBC during the network's 2009 transition, and then to Conan on TBS beginning in 2010, accumulating eighteen years across the three programs before departing in April 2015.
During his time with the Conan programs, Stack received five Writers Guild Awards and was nominated for more than twenty Emmy Awards, winning the Emmy for Outstanding Writing for a Variety, Music, or Comedy Program in 2007. In September 2015 he joined The Late Show with Stephen Colbert on CBS as a staff writer, a position he has held since. He has continued to perform as an improviser in New York, appearing monthly at UCB's Gravid Water show in Manhattan.
Historical Context
Stack's career trajectory represents one of the most sustained examples of the pipeline that moved Chicago improv performers trained in the Harold tradition into American late-night television writing. The ImprovOlympic cohort of the late 1980s and early 1990s, which included performers like Stack, Andy Richter, Adam McKay, Rachel Dratch, and Amy Poehler, became among the most consequential in the history of the institution precisely because it was the generation that matured under Del Close's most fully developed articulation of the Harold form before those performers dispersed into Second City and then into network television and film.
Stack's path through the ImprovOlympic to Second City's touring company and then directly to late-night television writing repeated a trajectory that defined the shape of American comedy infrastructure from the mid-1990s onward. The touring companies of Second City functioned as a transitional institution between the experimental long-form improv of the ImprovOlympic and the production demands of television variety writing, and performers who moved through both environments arrived in television rooms with both the narrative instinct developed through Harold training and the sketch economy required for broadcast formats.
His eighteen years across three Conan O'Brien programs constitutes an unusually long institutional commitment in a television landscape where writers' rooms turn over frequently, and his simultaneous maintenance of an active performing identity through UCB's Gravid Water show represents a sustained integration of improv performance with professional television writing that is relatively uncommon at his career stage.
Legacy
Stack's sustained career across three late-night programs gives him a distinctive position in the history of television comedy writing produced by the Chicago improv tradition. His collaboration with Adam McKay, Rachel Dratch, and Amy Poehler during the Second City GreenCo touring years placed him within a cohort whose collective influence on American comedy across the following three decades would be substantial: McKay became a major film director and producer, Dratch joined Saturday Night Live, and Poehler became a central figure at SNL and in the UCB Theatre's New York expansion. Stack's own trajectory into late-night writing provided one model for how the performance skills developed at the ImprovOlympic could be adapted into sustained television careers.
His Emmy win in 2007 and five Writers Guild Awards during his time with O'Brien's programs document a record of recognized achievement in variety writing that few improv-to-television performers matched across comparable time spans. His continued monthly performance at UCB Gravid Water reflects the broader commitment of Chicago-trained performers to maintaining active stage identities alongside their professional writing work, a practice that has sustained improv as a live performance form within the New York comedy community even as careers in television have drawn many of its practitioners away from the stage.
Early Life and Training
Brian Stack was born on August 18, 1964, in Park Ridge, Illinois, and grew up in Palatine. He studied telecommunications at Indiana University, graduating with Phi Beta Kappa honors in 1986, and earned a Master of Arts in Communication Arts from the University of Wisconsin-Madison in 1988. At Indiana University he met Mick Napier in an acting class. At Wisconsin-Madison he performed with the Ark Improvisational Theatre, an ensemble that included Chris Farley and Todd Hanson during his time there.
Personal Life
Brian Stack met the actress and improviser Miriam Tolan while both were performing on Jazz Freddy at the ImprovOlympic in Chicago. They married on June 1, 1996. The couple has two daughters, Nora and Colette.
Recommended Reading
Books are ordered from the strongest direct connection outward to broader relevance.

Yes, And
How Improvisation Reverses No, But Thinking and Improves Creativity and Collaboration
Kelly Leonard; Tom Yorton

The Art of Chicago Improv
Short Cuts to Long-Form Improvisation
Rob Kozlowski

The Second City Unscripted
Revolution and Revelation at the World-Famous Comedy Theater
Mike Thomas

Long Form Improvisation and American Comedy
The Harold
Matt Fotis

Improv Nation
How We Made a Great American Art
Sam Wasson

Group Improvisation
The Manual of Ensemble Improv Games
Peter Campbell Gwinn; Charna Halpern
References
How to Reference This Page
The Improv Archive. (2026). Brian Stack. Retrieved March 19, 2026, from https://improvarchive.org/people/brian-stack
The Improv Archive. "Brian Stack." The Improv Archive, 2026. https://improvarchive.org/people/brian-stack.
The Improv Archive. "Brian Stack." The Improv Archive, 2026, https://improvarchive.org/people/brian-stack. Accessed March 19, 2026.
The Improv Archive is a systemically maintained repository. The archive itself acts as the corporate author.