Stack got his start in comedy with the improv comedy troupe
The Second City in Chicago, working alongside fellow comedian
Amy Poehler.
''Late Night with Conan O'Brien'' Stack became a sketch writer on ''Late Night with Conan O'Brien'' in 1997 Stack first appeared onscreen when one of the writers asked him to play a doctor in a sketch in which he had no dialogue. One of the first characters he did on the show was Bathtime Bob the Hygiene Cowboy, who sang about bath time, but, like many of Stack's characters, there was a dark, tragic underbelly to his upbeat nature. Stack had previously tried to develop this character at Second City, but it never appeared in any shows. Stack played many recurring characters on the show, most notably those clad in anachronistic or elaborate outfits, and he was known for playing many characters with long beards and mustaches, such as God,
Zeus,
Socrates,
Gandalf,
Dumbledore, and
The Interrupter. Jeff Loveness of
Jimmy Kimmel Live has observed of Stack's characters that there was "such a sadness to each character, but they would not acknowledge their sadness", an assessment that Stack agrees with. Stack has further explained that, "My favorite kind of comedy on the late-night has always been the non-topical silly stuff where it's not really at anybody's expense. My least favorite kind of joke is a celebrity joke, because it tends to be very familiar or sometimes very mean, and if it's not mean it doesn't even work, usually...But my favorite kind of comedy on late night is at no one's expense but the character that's involved in the sketch where you're not really going after anybody." •
Ira (of Jeremy & Ira), performed with Late Night writer
Jon Glaser (as Jeremy), as two bizarre men from another dimension dressed in black hoods, who would visit Conan & Andy from time-to-time, always appearing in the corner of the TV screen. They never speak, and only communicate through nodding and other gestures. •
Kilty McBagpipes, an extremely stereotypical
Scottish man who dresses in a kilt and dances to
bagpipe music. •
Steve St. Helens, a stagehand on the show whose temper rises until he erupts. The character first appeared when
Mount St. Helens began showing activity in early 2005. Stack also created the recurring segment "
Pierre Bernard's Recliner of Rage", and his voice work on the show included providing the voices of numerous celebrities parodied in the
Syncro-Vox faux interviews conducted by O'Brien, including
Dick Cheney,
Mike Tyson, and
Martha Stewart.
Conan recurring characters Stack continued his work on O'Brien's TBS series,
Conan. His last episode aired on April 2, 2015, with Stack in a sketch as
The Interrupter where he and his character bade farewell to the series. Among his recurring characters: •
James Sinclair St. Wallins, Audiencey Awards fashion correspondent. •
Brian LaFontaine, singer on "Basic Cable
Name That Tune", who performs awful, thinly veiled alterations of famous songs to avoid royalty fees. Conan frequently expresses his contempt for this character, making comments such as "Hate that guy" or "Easily my least favorite person". •
Voiceover of Minty, the Candy Cane That Briefly Fell on the Ground, singing the theme song for "Minty the Candy Cane Who Briefly Fell on the Ground" (played by
Brian McCann). •
Joe Galliano,
John Galliano's 'brother' whom Conan interviews, generally in response to comments made by John Galliano. Joe tries to defend his brother while changing into ridiculous hats every time the camera switches back to Conan. •
WikiBear, the voice of 2014 recurring character "WikiBear", a teddy bear who has a vast knowledge of general knowledge questions asked by Conan, but who quickly veers off topic into tangents on very disturbing facts.
The Late Show with Stephen Colbert After fellow Second City alumnus
Stephen Colbert succeeded
David Letterman as the host of the
CBS series
Late Show, Stack left
Conan, and returned to New York to take a job on the
Late Show writing staff.
Voice work He provided voices for numerous characters in the video games
Deer Avenger (1998) and
Deer Avenger 2: Deer in the City (1999), which were written by Stack's fellow
Late Night writer/actor
Brian McCann, and which co-starred McCann,
Tina Fey,
Jon Glaser, and
Amy Poehler. In 2000, Stack played "Whiskers" in "Western Day", the December 6, 2000, pilot episode of
Robert Smigel's TV series
TV Funhouse. In 2011, Stack provided the voice of the lead Marmoset in
Rio. In 2012 Stack provided the voice for the Airplane Pilot in
Hotel Transylvania. Stack voiced the
CEO in the web series
Talking Tom & Friends. ==Personal life==