Cartoon Donald Trump has an IU telecommunications degree.
Brian Stack, BA’86, voices the “Late Show with Stephen Colbert” character on top of his main gig as a writer for the show. A lifelong love of comedy and degrees in telecommunications and communication arts combined to launch an Emmy Award-winning comedy writing and acting career.
Stack was first drawn to comedy as a kid, when he would watch ensemble sketch performances like “Monty Python” and “Saturday Night Live.”
“I never thought that I’d be able to do that myself,” he said. “But that’s what I wanted to do.”
As an IU student, Stack considered studying journalism, but ultimately pursued telecommunications — in part because he couldn’t type.
“I remember thinking, ‘I don’t think I can do the journalism class until I learn to type faster,’ and then I ended up taking a telecoms class,” he recalled. “I had fully intended to take typing and then go back and take all those journalism classes, and then just took a left turn and did telecom.”
At IU, he drew cartoons for the Indiana Daily Student and DJed at WIUS (now WIUX). He developed an interest in improv and standup comedy, but only as an observer.
“I didn’t have the guts to try improv while I was in college, but I got interested at IU watching my friend Mick Napier,” Stack said. “I used to go see his improv group at IU, and I loved it.”
As a communication arts master’s student at the University of Wisconsin, Stack finally mustered up the courage to give comedy a try. He performed improv at the Ark Theatre alongside other eventual greats like Chris Farley, who would go on to work at Second City, a legendary sketch and improv comedy club in Chicago.
It was in 1988 that Stack first saw Stephen Colbert perform, when he visited Chicago to catch a performance by Farley’s comedy troupe at the time.
“I had known Stephen even back in the Chicago days, but never expected that we’d be working in television, or that he’d be who he is, even though I always knew he was talented enough to be,” Stack said. “He was always a brilliant performer and writer, even in those days.”
For Stack, graduate school felt like a confluence of two separate lives. There was the day-to-day life of school and studies, and then there was the life of comedy. That dualism continued post-graduation, when Stack worked in an ad agency by day and moonlighted as a stand-up comic.
On weekends, he performed stand-up shows with friends.
“It was incredibly fun, but we weren’t making any money doing that,” he said.
In 1992, Stack was hired at Second City.
Stack’s telecommunications background became relevant again when he transitioned to television as a sketch writer for “Late Night With Conan O’Brien” in 1997, eventually stepping out from behind the camera to appear in a variety of sketches. It was still very much a learning experience, he said, both because so much had changed and because there’s no way to fully learn what it’s like to be on a television show besides, well, being on a television show.
Stack said resurgences like this were not an uncommon trend in his life as a comic.
“It’s interesting how a lot of the stuff I learned in school ended up coming back into my comedy in ways that I didn’t expect,” he said.
Taking courses on ancient Rome and working in an ad agency were, of course, not planned directions on Stack’s roadmap to comedy success, but they were detours he profited from, at first in education and later in having a wealth of experiences and knowledge from which to mine for good comedy.
“My mom used to jokingly call my dad and I ‘treasuries of useless information,’” he said. “But in improv and sketch, it’s amazing how a lot of that useless information becomes useful as references in sketches or in improv shows. If you can pull out something about ancient Rome when you’re in a scene about ancient Rome, it’s a lot of fun.”
When O’Brien moved to “The Tonight Show” in 2009, so, too, did Stack, who continued donning the guises of a slew of ridiculous characters. Among them were Kilty McBagpipes, Hannigan the Traveling Salesman, Frankenstein and even God.
Stack’s work with Conan O’Brien continued onto the TBS series, “Conan” until April 2015, when he bid the series farewell in a sketch as The Interrupter, one of his recurring characters on the show.
Stack returned to New York to take a job on the writing staff of “The Late Show with Stephen Colbert.” Among other characters, he lent his voice to the show’s cartoon rendition of Donald Trump.
In his later work, Stack said it’s vital for comedy to capitalize or reflect on current events. Sometimes it can provide a distraction from the world. Other times, it can be a lens through which to observe it.
“Ideally what we shoot for every night is to take stuff that’s alarming or scary or appalling and find humor in it so people can at least laugh at the people causing all those problems,” he said.
Even though he’s climbed the ladder from campus improv to live television performances, Stack knows there was importance to every rung.
“I’m grateful for all the jobs I had along the way,” Stack said. “It helps me understand, kind of, the broader landscape of workplaces. If the only job I’d ever had had been in television, I think I’d have a narrow worldview. It’s broader because I worked in all these places.”
Comedy is about creating something everyone can relate to, and that takes experience. It’s kept him funny, and it’s kept him humble as well. Although he’s among former idols, there’s still reverence.
“To this day, at ‘Colbert’ or at ‘Conan,’ if any of the ‘Monty Python’ people come on, even if the audience doesn’t necessarily know that much about them, I still get very starstruck,” Stack said. “They’re kind of like my Beatles and Stones.”