When Stephen Colbert breezed into town last month to shoot a segment at Buckingham Fountain for his soon-to-debut late-night program on CBS, he did so with uncharacteristically little fanfare—certainly far less than has greeted his other visits to Chicago throughout the nine-season run of Comedy Central’s The Colbert Report. In 2006, the Northwestern University graduate served as grand marshal of his school’s homecoming parade. A few years later he returned for the 50th-anniversary celebration of Second City, where he studied and performed from 1987 to 1994 alongside such future stars as Chris Farley, Steve Carell, and Amy Sedaris. He also delivered Northwestern’s commencement address in 2011, and emceed Lookingglass Theatre Company’s annual Gglassquerade benefit in 2013.
Does he miss paying CTA bus fare with small change, filled with what he has described as a mixture of humiliation and joy as the coins clink-clank-clink into the till? Not likely. These days he is chauffeured to work. It’s also unlikely that he misses waiting tables for tips at the now shuttered Danny’s Place on Michigan Avenue and Scoozi in River North, or assembling and selling what he once characterized as “horrible, horrible futon frames that fell apart on people in the middle of the night and left jagged bits of wood and four-inch, razor-sharp zip screws sticking into their mattresses.” As Colbert figures out how to fill David Letterman’s vacated desk, the source of his nostalgia is almost surely this: Chicago was for him, as it is and has been for so many other funny, ambitious people, a sort of creative safe zone where the concept of “we” trumped “I.” Where ensemble work was valued over solo showboating in what the late Second City cofounder Bernard Sahlins called the “theater without heroes.”.
Upon graduating from Northwestern, where he majored in theater, Colbert was accepted to drama school in New York but forwent it to act for a year in Chicago. Awakened early each morning by an alarm that sounded like a foghorn, he worked the breakfast shift at Blind Faith Cafe in Evanston, near half of a duplex he shared with Libera and several others at 2015 Ridge Avenue, and appeared with the Journeymen Theatre Ensemble, where he was credited as Stephen T. Colbert—Tyrone being his middle name. The fledgling company’s productions, staged at Raven Theatre in Rogers Park, included the double bill of an original play called Service With a Smile and an improvisational piece titled Come as You Are, both of which were panned by Chicago Tribune critic Sid Smith in a review that made no mention of Colbert. He also acted in a kid-oriented courtroom production called Rumpelstiltskin v. the Queen that toured Chicago schools in partnership with the Cook County Circuit Court (Colbert played the part of the miller), and joined the Evanston-based Trinity Square Ensemble for Lavonne Mueller’s Little Victories. None made him a household name beyond his own house. “I’m definitely a performer who learned how to write because that was the only way I would get cast,” Colbert said in a recent installment of the Late Show podcast. “I just couldn’t get arrested in Chicago. I couldn’t get a gig.” Not a well-paying one, anyway.
How Chicago shaped Stephen Colbert#
When Colbert reapplied to grad school the following year, he was turned down. “Then I really went into a slough of despond,” he said on his podcast. “I was like, ‘Oooh, I have ruined my life.’ And right then is when I started to improvise.” More frequently, yes, but he’d actually been introduced to the art of devising scenes on the fly with his Northwestern improv group the No Fun Mud Piranhas. They also trekked to a place called Crosscurrents, the precursor to iO Theater, beneath the Belmont el stop in Chicago, where such masters of the craft as Del Close and David Pasquesi practiced a long-form “game” known as the Harold, and iO cofounder Charna Halpern coached Colbert’s team in a Harold competition between several colleges. (Interesting side note: When in 2005 the U.S. Olympic Committee threatened to sue ImprovOlympic for trademark infringement and forced a name change, it was Colbert’s brother Ed—a partner and intellectual property attorney at Kenyon & Kenyon law firm in Washington, D.C.—who, as Colbert has said, “brought the hammer down.”) Colbert was intrigued with improv and kept performing at Crosscurrents every Tuesday for about a year after graduation, in the process recognizing that “it’s possible to make discoveries onstage and not be a poet-jerk about it.”
As he continued to imagine for himself a life on the stage, Colbert grew increasingly comfortable with comedy. He began to realize that his theatrical chops and his recall for things read and heard—books, Bible passages, songs—were perfect complements to his sense of humor, which ranged from silly to subversive. His general outlook was brightening as well. “I was 22 or 23 when I made a decision not to be actively Hamlet-like and miserable in my daily life,” he told Rolling Stone in 2009. Besides improv, he found solace in spirituality. Raised in a staunch Catholic household, he’d sometimes been a daily communicant but had fallen away from his faith during college. The catalyst for his reawakening was a chance gift. A member of the evangelical Christian association Gideons International “literally gave me a box of The New Testament, Psalms and Proverbs on the street in Chicago,” Colbert said in Rolling Stone. “I took one and opened it right away to Matthew, Chapter 5, which is the opening of the Sermon on the Mount. That whole chapter is essentially about not worrying. I didn’t read it—it spoke to me, and it was an effortless absorption of the idea. Nothing came to me in a thunderbolt, but I thought to myself, ‘I’d be dumb not to reexamine this.'”
He reexamined Second City, too. Having arrived there with no desire to work on one of its stages and an improv purist’s wariness that soon disappeared, Colbert ended up auditioning for and was invited to join the theater’s newest of three touring companies, dubbed GreenCo. As a member of that troupe and then of the more advanced BlueCo, which toured nationally, he performed classic Second City scenes with castmates who initially included the late Chris Farley and developed a keen sense of what he referred to in an A.V. Club interview as “scenic structure and dramatic gambits that work, and things that are appealing both as a performer and an audience member.” In other words, he found his comedic strengths and preoccupations. “I became obsessed with status behaviors,” Colbert said in a 2008 conversation for my book The Second City Unscripted. That focus was rooted in the teachings of improv guru Keith Johnstone. “Like a lot of people, I wanted to be high-status. And so I started doing super-low-status characters. I did this guy named Charlie, who had a terrible sort of stutter. He wasn’t mentally disabled, but he was pretty weak.” In that vein, Colbert began challenging himself, asking, “Will I allow myself to be a fool onstage? Will I allow myself to be unattractive? To be stupid? Obnoxious? Or will I stay in these khakis and button-down shirts?”
When Colbert was truly upset about something, which seems to have been a rare occurrence, those around him knew it. “He was always a gentleman. Always a gentleman,” former Second City castmate Fran Adams says. “And there was one moment in frustration when he was not, but we realized he was just having a very bad, dark day.” When he did get bent out of shape, it was often about some aspect of the work that was faltering. Case in point: After an exceedingly poor improv set one night, castmate Jackie Hoffman expressed indifference and flippantly uttered the phrase “I don’t care.” Colbert became incensed: “You don’t care? You don’t care?!” He later apologized for the outburst.
Between dramatic turns, it was back to touring and waiting tables. Danny’s closed sometime in ’89, and Colbert moved on to the River North Italian eatery Scoozi, where he worked lunch shifts and wore a snazzy gold jacket. Many of his comedy cohorts worked at restaurants, but Colbert’s gig was on another level. “Everybody else worked at a joint,” Adams says. “Stephen worked at Scoozi. He knew the true meaning of al dente, and grana padano versus Parmigiano Reggiano.” At one point he taught her how to cut a cheesecake with dental floss to achieve perfect slices. In a 2010 post on Daily Kos headlined “A Man of Character,” a person going by the handle “Behan” claimed to have worked as a Scoozi busboy while Colbert was a server at the restaurant. Compared to the dinner hours, when more employees were on hand to help out, daytime “was horrendous” for nonservers. “At this time, the main waiters would gab about auditions that they were up for in films like Uncle Buck,” Behan wrote. But not Colbert, who “helped . . . with all sorts of tasks that weren’t his responsibility,” including busing tables. According to the anonymous commenter, Colbert also befriended a few Ecuadoran busboys with whom he spoke Spanish, and was learning Italian from an immigrant coworker. The busboys, Behan wrote, referred to Colbert as “buena gente” (good people). When it came to sharing his tips, Colbert was uncommonly generous and as a consequence was considered “the best waiter to work with. He commanded loyalty.”
In April 1992, Colbert and a cast embarked on Second City’s first-ever visit to Europe, where they performed in Vienna, Austria. A few months after returning home, they opened their second show at Northwest, and by late that summer Colbert had been promoted to the company’s E.T.C. stage on Wells Street for his first and only revue there, Where’s Your God Now, Charlie Brown?, which opened in September. “That cast was pretty fucking amazing and we loved each other so stupidly much,” says David Razowsky, who was one of Colbert’s best scene partners. “We just laughed backstage and the audience was secondary to anything we were doing.” Both he and Colbert were then seeing psychotherapists, Razowsky says, so they wrote a scene about an uninterested shrink and his patient that was inspired by their common experience. When sketches tanked, Razowsky adds, they were all in the shit together.
His condition improved. In March 1994, Second City debuted what would be Colbert’s final main-stage show, Are You Now, or Have You Ever Been Mellow? The Trib‘s Smith began his assessment of it with a less-than-encouraging line: “So what happened to the Wells Street brain trust when time came to come up with this new one?” Fortunately, things took a turn for the better, with Smith praising the show’s “enviable energy” that “scarily covers the bases of performance comedy.” He saved his most generous remarks for the cast, describing them as “terrific” and extolling their “seasoned skills.” The Reader‘s Lawrence Bommer was generally positive as well, though he was puzzled by “a weird scene in which Christ [played by Colbert] appears in the crisper of a communal refrigerator.” Bommer had no idea why it ended “with a dippy ballad about how the world would be better if it were a Boston chicken turning on a spit.”
