Colbert in 1987 at the Second City Training Center Credit: Courtesy of Second City

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.

This time around, however, almost no one outside The Late Show With Stephen Colbert‘s inner circle knew the comedian was coming. After the short taping, a few spectators who happened to be in the vicinity approached him to say hello and pose for photos. Dressed in a slim-cut dark suit, the 51-year-old was gracious, accommodating, and in fine spirits—no doubt happy to be back in his erstwhile home, if only briefly. For while the comedian left Chicago more than two decades ago, Chicago has never left him.

Born in Washington, D.C., and bred in Charleston, South Carolina, Colbert has long lived and worked in New Jersey and New York. But Chicago is his creative birthplace—the town where this once serious-minded thespian and emotionally wounded young man discovered his comedic calling. Despite his professional triumphs—especially over the past decade as the host of The Colbert Report and before that as a correspondent on The Daily Show With Jon Stewart—he has stayed mindful of those formative years and often mentions them during interviews.

He did so in the lead-up to The Late Show, which debuts September 8, hosting a short weekly podcast that features Late Show staff discussing everything from comedy to music to their backgrounds. In a two-part episode titled “What Do You Think It’s About Chicago?,” Colbert spoke glowingly and wistfully of his eight-year Chicago tenure, which began after he graduated from Northwestern in 1986 and ended when a Comedy Central sketch show called Exit 57 lured him to New York. Colbert’s trip down memory lane wasn’t blatant pandering of the sort that came so easily to his bloviating and recently retired Colbert Report character. It seemed genuine, deeply felt. “I miss it so much,” he said of the city.

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.”.

“There are very few rules to improvisation, but one of the things I was taught early on is that you are not the most important person in the scene. Everybody else is,” Colbert said in his Northwestern commencement address. “And if they are the most important people in the scene, you will naturally pay attention to them and serve them. But the good news is you’re in the scene too. So hopefully, to them, you’re the most important person, and they will serve you.”

For Colbert, Chicago is as much a place rife with colorful characters as it is a state of mind, in which the chief concerns aren’t ratings or budgets or marketing. (“I learned a lot from some of the guys who . . . had had a career in Gary,” he has said of early fellow improvisers, “and they made great jokes about, like, the inorganic noncombustible particulate matter count.”) Chicago provided, in short, the purest creative experiences of his life, without which he may well have followed a different and far less comedic path.

That Colbert would achieve eventual success in whatever he did, those who know him say, was never in question. Colbert’s friend and former college roommate Anne Libera says Colbert knew he was destined for something greater. But that conviction never veered into grandiosity, “because it was always leavened with this jester [quality], with a humbleness. There was never a sense of entitlement.”

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.

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.”

Mind-expanding and revelatory though improv was, Colbert still envisioned his future as a bearded New York actor who lived alone “in some sort of open, large but sparse studio apartment with a lot of blond wood and a futon on the floor and a bubbling samovar of tea in the background.” He didn’t want to merely play Hamlet, he has often said of his early artistic bent; he wanted to be Hamlet—an angst-ridden artiste who “wore a lot of black” and would readily “share my misery with you.” Though he didn’t often open up about it, even among close friends, Colbert’s “misery” was rooted to a large degree in psychological trauma caused by the tragic deaths of his father and two brothers. In the early morning hours of September 11, 1974, their Eastern Airlines plane crashed in a cornfield on approach to what is now Charlotte Douglas International Airport in North Carolina. Pilot error was to blame. Colbert, the youngest of 11 children, was ten when it happened, and during his childhood he had never really dealt with the emotional ramifications of that shattering event. For the next eight years, with his older siblings out of the house, he had lived with only his grief-stricken mother and tried his best to make her laugh. College, first at Hampden-Sydney in Virginia, then at Northwestern, had given him plenty of time to ruminate on his tremendous loss. He sank into a depression that, though it seemingly became less acute at Northwestern, lasted through his early 20s.

Thanks to Libera, who worked at Second City, where today she’s director of comedy studies at the theater’s training center, the financially strapped Colbert was hired to answer phones at the box office and moved into a nearby apartment. He also sold Second City T-shirts, and as a perk of the job was able to take improv classes for free. In workshops led by sage instructors including Don DePollo, Martin de Maat, Jeff Michalski, Michael Gellman, and a twentysomething named Mick Napier (cofounder of the now venerable Annoyance Theatre, with which Colbert had been involved during his time at Crosscurrents), he was schooled in techniques—listening closely, never denying, being in the moment—that would inform his work for years to come. “He was pretty good right away,” Napier says. As a consequence of Colbert’s intellect, “he had a vast amount of resources available to him . . . and was brilliant at finding the funny of a scene or the irony of a scene or the game of a scene.” Napier, Colbert said, taught him “boldness, freedom. You throw away your mind. Be in the moment. Don’t give a shit about what people think of you. Come through the door. Don’t apologize for your actions onstage.” A Second City cast member from the early 80s named Rick Thomas offered Colbert insight as well: “Your responsibilities [onstage] are to see and be seen, to hear and be heard—and to feel and be felt.”

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?”

Because work with a touring company paid little and could be sporadic, particularly during the summer, Colbert redeployed his skills as a waiter at a just-opened Michigan Avenue restaurant owned by Danny Coval, the brother of Second City producer Joyce Sloane. Danny’s Place, which served a variety of global cuisines, was yet another venue where Colbert could play a part while serving others, a key tenet of improv. “If he would never have made it in comedy, he could still be waiting tables and making a lot of money at Gibsons,” says Coval, who “got a lot of compliments” about Colbert from patrons.

Back at his night job, whether during Monday touring company shows in Second City’s main-stage space on Wells or in other places around the country, Colbert’s comedy education and infatuation intensified. Perhaps most valuable of all, he learned to accept failure for what it was: no big deal. There was always another show. If scenes went south, director Ron West remembers, Colbert devised a phrase, “coffee specialties,” that signaled the stage manager to kill the lights and end the horror. “When I did straight theater,” Colbert said, “I would come backstage, and if the scene hadn’t gone well or if there had been a fuckup onstage, there would be a lot of people looking in their mirrors, kind of patting [on] their powder and saying, ‘How’s it going out there? It seems kind of quiet.'” If he screwed up at Second City, on the other hand, he could hear his costars “mocking me at the top of their lungs from the wings.” He’d found his tribe.

Although Colbert had lightened up considerably, he took his “stupid seriously” and was mature beyond his years. “He did seem like the adult when we were all children,” Colbert’s GreenCo castmate Tracy Thorpe says, “but never in a ruin-the-fun way.” Several people recall his stepping in when an older Jewish woman strongly objected to the cast’s performance of a classic short “blackout” during which the audience was encouraged to hum in unison before splitting into sections for a humming competition. The kicker: “And you wonder how Hitler took power.” There was nothing funny about Hitler, the woman insisted. “I apologized, and talked with her for like 15 minutes,” Colbert said. “She was very upset.” The rest of the cast had been hiding in a nearby bathroom, waiting for him to quell the unrest. When she left the room, Colbert turned around and announced, “All right, you can come out now.” “He was so composed with this woman, who was kind of crying and screaming at him,” former castmate Rose Abdoo says. “And he was just very, very polite. You could not get mad at him because he was so polite.”

An early Colbert headshotCredit: Courtesy of Second City

Colbert’s even-keeled disposition made him virtually unflappable, those who worked with him say, whether during an argument or while waiting to go onstage. During her touring company debut, Thorpe says, she and Colbert kicked things off with a “very, very odd, nonsensical” two-person scene. As she stood with him in the wings beforehand, more petrified than she’d ever been, Thorpe looked at Colbert and noticed an honest-to-god twinkle in his eye. He couldn’t wait to get out there. “It was like, ‘Come on! We’re just gonna go have fun!'” she says. “And it just melted all that [fear] away and reminded me that it’s really not brain surgery. We are just going to go out and play make-believe. It was the greatest gift I could have ever gotten in the moment, and I’ve never forgotten it.”

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.

During his early touring days, Colbert’s romantically involved costars Amy Sedaris and Chicago-born Paul Dinello (a former member of the Colbert Report team, now a Late Show supervising producer and writer) were instrumental in loosening him up. Whereas Colbert was at first very controlled, tending toward an overly tidy and intellectual approach to scene work (they gave him the nickname “Reference Man” due to his steel-trap memory), Sedaris and Dinello took a goofier, more emotional tack. Before long the three formed a tight triumvirate who often hung out and were perpetually brainstorming. They would later create and star in three seasons of the Comedy Central series Strangers With Candy, and its 2005 film adaptation.

“He was very serious in the beginning, and it was hard,” Sedaris said of Colbert during a conversation in 2008. “But after that, he was all ours.” Dinello, also in an ’08 chat, said Colbert initially regarded him as “a drunk philistine.” But his and Sedaris’s unbridled silliness and merciless needling had the effect of chilling Colbert out. Eventually. When he asserted, for example, “I never laugh onstage,” Sedaris furtively installed gross false teeth for a musical scene in which several guys launch into a seemingly romantic doo-wop ode that turns sexually suggestive and braggadocious. “Pardon me, I couldn’t help noticing you standing there,” Colbert began crooning to Sedaris, who smiled to reveal her ridiculous fake chompers. Colbert cracked up. “I was so mad at her,” Colbert said. “I was really, really mad. “This was pretty early on in our relationship, and she and Paul really thought my tie was tied too tight, and she wanted to break me.” It worked. “I fucking blew offstage and went and locked myself in the bathroom like a teenage girl, and banged my head against the wall with rage,” he recalled in The Second City Unscripted. That only delighted Sedaris and Dinello, who knocked on the door and asked, “Are you crying in there?” Colbert soon realized how lucky he was to have met them, these “two people to love and be loved by for the next few years. Because it’s not easy to be a lady-in-waiting at Second City.”

The cast of Second City Northwest’s Destiny and How to Avoid It: Nia Vardalos, Ian Gomez, Mitch Rouse, Colbert, Amy Sedaris, and Paul DinelloCredit: Courtesy of Second City

Despite assimilating into the comedy and improv spheres, Colbert had yet to relinquish his actorly ambitions. Taking several leaves of absence from touring with Second City, he starred or costarred in at least four plays over the next year, beginning in early 1989 with a small role in The Enormous Room at the now defunct Next Theatre Company in Evanston. Adapted from a World War I memoir by E.E. Cummings, it earned an excellent review from Sun-Times drama critic Hedy Weiss. Colbert then joined fellow Northwestern alum and budding theater artist Dexter Bullard for a production of Bullard’s one-act, fully improvised creation Schumacher. Staged at the Playwrights Center on Clark Street in Wrigleyville, Schumacher was intended as a metaphor for viral infection in which Colbert portrayed a hard-driving salesman (the cell-invading agent) from whose name the play’s title is taken. Reader critic Tom Boeker was complimentary. Colbert, he wrote, gave an “inspired if somewhat wired performance” in which he managed to be alternately “condescending, ingratiating, and outright manipulative without ever losing his sheen. The only time he seems rattled is during the brief audience involvement—which he solicits well enough, but doesn’t know how to handle when he gets it.”

A month or so later, Colbert was alone in the spotlight for a play titled Describing a Circle. Directed by his friend Libera, it was staged in a venue that was also hosting a Live Bait Theatre production whose set included (fortuitously) a giant circle as well as a slide. Comprising short stories and other pieces Colbert had written—including a phone conversation between Jesus and God that Libera likens to “a one-man Abbott and Costello routine”—the simple question at the heart of Circle’s premise was this: What happens when you leave a man alone onstage? Well, for one, he plays on the slide. Two more Bullard collaborations followed, including the playwright’s original Infusoria (based on a morality play by Henrik Ibsen) and future Czech Republic president Vaclav Havel’s supposedly funny 1968 work The Increased Difficulty of Concentration, both at Next. “It couldn’t have been more boring subject matter that he made completely fascinating,” says Abdoo of the Havel play.”Dex built a big Vaclav Havel head, a la Terry Gilliam,” Colbert told the Tribune in 2004, “and we rigged it with a spring-loaded mouth. We wrote a prologue where I did the voice, educating the audience that this was a comedy, what to expect. And it worked! It changed the reaction of the audience completely.” Colbert was a top-notch front man, Bullard says. Besides his formidable brainpower and improvising skill, he was playful and had an “incredible listening ability.” He also possessed “a kind of sex appeal that was different and interesting” as a result of his “romantic, nerdy, and genteel” nature.

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.”

Steve Carell (top left) and Colbert meet the BeatlesCredit: Courtesy of Second City

In the late spring of 1990, Colbert returned to his hometown of Charleston to attend the Spoleto Festival USA, an offshoot of the annual Festival dei Due Mondi (Festival of Two Worlds) in Spoleto, Italy. The 17-day extravaganza, in which Colbert had participated as an opera extra during high school, features scores of performances by emerging and established artists in an array of fields: dance, classical, theater, opera, and jazz. It was there that Colbert met his future wife, Evelyn McGee, to whom he has now been married for nearly 22 years. Spying her across a theater lobby, he told Playboy, “I thought, Oh, wow, there’s my wife.” The daughter of a prominent Charleston attorney, McGee had double-majored in drama and English at the University of Virginia and was also an actress. Despite having grown up mere blocks from each other, she and Colbert had never met. After a long stretch of courting by letter and phone, the two began dating and eventually McGee moved to Chicago, where she worked as development director for the now defunct Remains Theatre. Aaron Rhodes, one of Colbert’s touring company cohorts, remembers sitting at a bar one evening as Colbert told him about meeting Evie (pronounced EH-vee). “Aaron,” he said, “how do I tell her she is the cow of my every field?” The unfortunate use of “cow” notwithstanding, he was obviously smitten. Calling McGee “lovely and accomplished,” Libera theorizes that finding her was, “without it being in any way creepy, like finding his mother. It was like finding that person who made perfect sense.” McGee was also, Libera thinks, an important connection to Colbert’s southern cultural roots, “to aspects of himself he might have been afraid he was going to lose”–though in a more passive way than he’d willfully shed his accent by imitating television news anchors as a child. In any case, he was a man entranced.

Careerwise, though, Colbert felt stymied. It was 1991, and after more than two years of touring performances with Second City, he was doubtful that he’d ever be promoted to one of Second City’s resident companies, which would give him a higher-profile showcase, regular hours, and better pay. And so he told Sloane that his leaves of absence were over; he was splitting for good. To which she replied, “I don’t respond to threats.” But it wasn’t a threat, Colbert assured her. Although he loved working at Second City, he felt that staying much longer might change that and he didn’t want to “become one of those people who feels like they wasted their time.” Sloane understood his concern. “The next day,” Colbert said, he was tapped to be an understudy, and in December of that year he debuted his first original show, Ku Klux Klambake, at Second City’s suburban theater in Rolling Meadows (an outpost known as Northwest) alongside castmates Dinello, Sedaris, Hoffman, Scott Allman, Ian Gomez, and Nia Vardalos. Directed by one of Colbert’s first improv teachers, Napier, it included some dark material that satirized (among other subjects) hunting, racism, and Central American politics. “The theme of an ungrounded society is expanded in a couple of outstanding scenes,” Sun-Times critic Weiss noted in her review. “In one, Stephen Colbert plays a lonely mailroom clerk who keeps interrupting coworker Paul Dinello’s attempt to crack a stupid joke. Colbert hallucinates that Dinello is Jesus Christ. Between Colbert’s zealotry and Dinello’s embarrassment, the pair form a wonderful team.” Writing for the Reader, Jack Helbig deemed Klambake “a stronger show than we’ve seen at North and Wells in quite some time.”

Although Northwest had far less cachet than Wells Street, it enabled Colbert to cocreate entire revues from scratch rather than merely repeat golden oldies from years past. Relationship scenes were common, and he made a conscious effort to avoid material about politics or popular culture. Anything that was happening on those fronts, he has said, held no allure from a performance perspective. “We kind of had a little bit more freedom [at Northwest],” Sedaris recalled. “The audiences were harder. They were really mainstream. But we had to make each other laugh. I don’t remember ever going out there thinking, ‘Oh, god, the audience,’ because we could have our fun onstage. Whoever was in the scene would be the audience, so you kind of played to each other. So it was a great place to be, because nobody was out there checking up on you. We were far away from it all.” Cheryl Sloane, Joyce’s daughter, produced Northwest shows during Colbert’s tenure and says the work he and his crew did “was really an expression of the cast” and flourished in the general absence of critics, who weren’t as likely to visit the burbs. “He loved what he was doing,” Sloane says, and it showed.

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.

One such instance had a special and lasting effect on Colbert, who reveled in the cast’s feeling of solidarity. As he remembered it, castmate Jenna Jolovitz went out onstage to perform a short blackout called “Whales,” which was supposed to begin with her preciously telling the crowd, “I’d like to do a song for the whales.” She would then take a beat, tune up, and begin making a series of bizarre, whalelike noises, which unfailingly got laughs. As Colbert and Razowsky stood backstage, ready to perform after Jolovitz finished, they waited for the laughs. None came. Instead of her usual setup, Jolovitz had said only, “I’d like to do a song.” No mention of whales. Patrons were understandably puzzled, then, by her odd utterances. And while she attempted to backtrack and correct her mistake, it was too late. “Dave and I looked at each other and opened our eyes and mouths wide with joy at her failure,” Colbert said. “Because we knew what had happened, but the audience didn’t.” Nearly convulsing by now, the castmates embraced and “fell to the floor in a paralyzing weakness of laughter. We just rolled on the floor, hugging each other and banging our feet against the wall, all of which can be heard out in the house.” Jolovitz was laughing, too–she couldn’t help it. In that moment, Colbert thought, “If this is how failure makes me feel, then I have to do this for a living.” Still, he would be tempted to defect once more for a dramatic role in the months ahead.

Ruth Rudnick, Colbert, Scott Allman, Jackie Hoffman, Steve Carell, David Razowsky, Fran AdamsCredit: Courtesy of Second City

When Colbert finally gained a firm foothold on the Chicago comedy mountaintop, Second City’s vaunted main stage, in February 1993, he was eminently comfortable–in his own skin and with his costars. He finished out the run of Truth, Justice, or the American Way for just-departed cast member Michael Clayton McCarthy, whom he’d been understudying. Around that time comic mastermind Robert Smigel, who had been impressed by Colbert’s understudy work while scouting talent for Saturday Night Live, introduced him to Conan O’Brien, who was looking for writers for his forthcoming late-night talk show on NBC. As with SNL, Colbert failed to make the cut. “Conan didn’t quite see how Colbert could fit in,” Smigel told GQ.

But Colbert had plenty yet to do at Second City, where several members of his new main-stage company had been together since their touring days. Joining standout Steve Carell, they staged a politically tinged revue titled Take Me Out to the Balkans, which opened in June. “The cast is ready for the big time,” Sun-Times writer Ernest Tucker declared, “and audiences are lucky to watch them guide the journey through America’s landscape, working together more smoothly than any other group on the political scene.” By this point in his comedic development, Colbert “had no problem showing up for a scene without his pants on,” Dinello, one of the seven main-stage members, said when we spoke in 2008. “He completely tossed the rules away.” That sort of boldness, supported by the fundamental “always agree, never deny” rules of improv, sometimes encroached on everyday life. During one outing at a dance club, Colbert bet Dinello and another friend he could convince a beautiful woman at the bar that he was a modeling agent on the hunt for talent. And so, with the help of a real modeling agency’s business card Dinello had procured, he did just that—while wearing sweatpants. On another occasion, Dinello remembered, they attended a party with “people from the outside world” where a well-dressed middle-aged woman was holding a paper plate piled with food. Dinello told Colbert to knock the plate out of her hands. “And he just walked over and slapped it out of her hands. He didn’t bat an eye. He felt awful. He said, ‘Oh my god, I’m so sorry. Let me fix you another plate.’ She was so confused.”

That summer Libera and Colbert took a long walk through the area just south of the Lincoln Park Zoo. During their stroll, she says, he expressed some apprehension over his future. Having become engaged to McGee in the previous months, he felt an increased sense of responsibility and pressure to be a breadwinner. After Colbert and McGee wed in Charleston early that October, in what attendees say was a proper and grand affair at the bride’s family home, the newly betrothed couple returned to Chicago and lived in a lovely 15th-floor penthouse apartment they’d found on the 2700 block of north Pine Grove Avenue in Lincoln Park. “I used to say to them, ‘When you guys move, can I have this place?'” castmate Ruth Rudnick says. “But it wasn’t just the place. It was the actual environment they created. They had dinner parties and they had people over. They had beautiful furniture that matched. Meanwhile, I had a couch with a blanket on it. I just thought, ‘Wow, look at them. Aren’t they lucky that they have this world with each other?'”

Life and work had never been better. Colbert was married to a wonderful woman and killing onstage. But he was faced with a predicament when Lookingglass Theatre came calling. Founded in 1988 by some of Colbert’s college acquaintances, including future Friends star and fellow No Fun Mud Piranha David Schwimmer, the nascent troupe was preparing to stage an adaptation of Russian writer Mikhail Bulgakov’s classic novel The Master and Margarita at Steppenwolf Theatre’s studio space, and around late summer or early fall Colbert was asked to join its cast. Then-Second City associate producer Kelly Leonard says he and Colbert discussed that possibility, but Leonard remained neutral lest his urging Colbert to stay have the opposite effect. “I think he still conceived of himself as a theater artist and didn’t necessarily want to be hemmed in,” Leonard says. Nonetheless, Colbert declined Lookingglass’s offer. It’s unclear whether his doing so stemmed from a decision he’d recently made to accept no more low-paying jobs (Lookingglass member David Catlin says the stipend, if there was one, would have been maybe $200 for the entire rehearsal process and run), or the realization that comedy better suited his skills and sensibility. “I was disappointed to not have [Colbert] in the [play],” Catlin said in an e-mail, “but understood that his particular extraordinary gifts were pulling him on a different and important path.”

Colbert’s decision weighed heavily on him. “I realized I wanted something like a normative life,” he later recalled in an interview with Howard Stern. “I realized, ‘I want kids and I don’t want to be traveling all over the world to go to this gig and that gig.’ And I had a complete nervous breakdown. I literally had to be medicated. . . . It’s like my skin was on fire a month after I got married.”

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.”

The most iconic scene to emerge from that revue–one that was reprised to great effect during Second City’s star-studded anniversary blowout in late 2009—was the absurdly hilarious and oddly touching “Maya.” Its premise: when Colbert returns to his southern hometown, he becomes a kindly old black woman named Shirley Wentworth—much to the puzzlement of his pal Steve, played by Carell. Inspired by his reading of Maya Angelou’s poetry and music by the all-female gospel sextet Sweet Honey in the Rock (to which he’d been introduced by his wife), Colbert said he’d begun thinking to himself, “I wish I were an old black woman! They have so much character. I’m so characterless. There’s no flavor to me. Who would be interested in me as a person?” That planted the seed for the improvisation from which “Maya” sprouted. “It absolutely came out of us as a group fully formed, and we did not change any of it,” Colbert said. Razowsky portrayed Colbert’s sheepishly smitten gentleman friend Nathan. “Certainly you’ve come back to accept my marriage proposal,” he tells Shirley, who says she has not. A few minutes later the awkward tension is broken as their lips lock in a tender and lingering kiss. According to Razowsky, with whom Colbert mashed faces scores of times, “His lips are very soft and he gives the right amount of pressure in the kiss to make it worth the while.”

On May 22, 1994, nine days after his 30th birthday, Colbert took his final bow as a Second City cast member. He’d spent about six years incubating–learning, creating, failing—and now it was time to leave the place that “was everything to me.” His comedy soul mates Sedaris and Dinello had already departed, and before long he joined them in New York to write for and act in an off-kilter Comedy Central show called Exit 57, while maintaining residency in Chicago. Evie, pregnant with her and Colbert’s first child, left Remains that spring. Soon the three of them headed east for good.

But wherever he is, Colbert carries Chicago with him. In choosing to pursue sketch and improv, the Chicago school of comedy, over the traditional dramatic stage, he told Charlie Rose, “I surrendered my need for importance. I surrendered my need to have status.” He has enjoyed both in abundance, of course, but even as the self-described “control freak” host of his own late-night program, he remains a team player who holds fast to “this idea that he is not the center,” Libera says.

“He is the hero, but he is not the center. He’s there to serve.”  v