Long before they were two of the most celebrated figures in modern Hollywood—dominating primetime sitcoms, Oscar-nominated dramas, and late-night television—**Steve Carell** and **Stephen Colbert** were struggling young improvisers on Wells Street in Chicago. In fact, when Carell first joined The Second City Mainstage in the early 1990s, he had a very specific job description: he was **Stephen Colbert’s understudy**.

Together with peers like Paul Dinello and Amy Sedaris, Carell and Colbert helped forge a golden era of Chicago comedy that launched an alt-comedy revolution.

The Second City Mainstage (1991–1993)

When Colbert was promoted to the Mainstage cast of Second City alongside Dinello, Carell was hired as the alternate understudy. Rather than fostering bitter rivalry, the relationship cemented an immediate, lifelong brotherhood:

  • Complementary Comedic Styles: Carell possessed an innate warmth and innocent vulnerability (which would later define Michael Scott on The Office), while Colbert excelled at razor-sharp intellectual pomposity.
  • The Improv Workout: On nights when both were in the cast, Dinello, Colbert, and Carell would push improvisational scenes to extreme limits, testing each other’s endurance and timing.

‘The Dana Carvey Show’ (1996)

In 1996, ABC took a massive gamble by greenlighting a primetime sketch comedy series created by Dana Carvey and Robert Smigel: The Dana Carvey Show. Carvey and Smigel raided Chicago for the sharpest young comedic minds in America, hiring Colbert, Carell, and bringing Dinello into the writers’ orbit.

It was on this legendary, short-lived show that Carell and Colbert debuted their iconic recurring sketch: “The Waiters Who Are Nauseated by Food.” Playing two elegant French waitstaff who dry-heave violently at the mere mention of soup or salad, the sketch remains a touchstone of pure physical comedy.

Reunited on The Daily Show with Jon Stewart

In 1999, Jon Stewart took over The Daily Show on Comedy Central and quickly hired Colbert as his senior political correspondent. Shortly thereafter, Colbert championed Carell to join the news team.

Throughout the 2000 election cycle and the early 2000s, Colbert and Carell’s “Even Stev-en” debate segments—where the two correspondents shouted increasingly ridiculous, personal insults at each other across split screens—became the signature comedic segment of the program.

An Enduring Circle of Loyalty

Decades later, despite Carell becoming an A-list movie star and Colbert becoming late night’s king, their Second City bond remains unshakable. Carell frequently appears as a guest on The Late Show with Stephen Colbert, where supervising producer Paul Dinello often greets him backstage with the same Chicago warmth they shared forty years ago.

Continue Reading