For some in Chicago, the anointing of Stephen Colbert as the successor to David Letterman this month was a watershed, greatly-to-be-savored moment of total establishment dominance by the Chicago comedy school — as propagated by such venerable institutions as The Second City, iO, the Annoyance Theatre and the Chicago Improv Festival, and their various spinoffs, ensembles and gurus.
Chicago has no significant claim on Jimmy Fallon, the charming new host of "The Tonight Show." But it does on Colbert. And on Seth Meyers. And Tina Fey. And Amy Poehler. Et cetera. In fact, after Letterman retires, on a date yet to be specified, performers who cut their teeth in Chicago will sit in two out of three of network TV's most historically prestigious comedic seats — Colbert at CBS and Meyers at NBC. Meanwhile, Fey, whose portfolio and influence yet are broader and more flexible, is in a place to do pretty much whatever she wishes in the whole wide world of comedy, be it live, on television or on film. Poehler is not so far removed from that position.
Why has this happened now?
On one level, this circumstance is no more complex than that quartet of names representing unusually abundant talents. Chicago has thousands of young people studying and practicing comedy and theater, and several universities and other entities that make a specialty of teaching those disciplines. There is no reason to be surprised when a small group of them make it big, nor to assume that there must be something in the water.
Still, there's more to it than that. Those Chicago-area schools (both Colbert and Meyers went to Northwestern University) provide the impetus for much of this talent to move here in the first place (Meyers was born in Evanston but raised, like the other three, outside of the Chicago area.) People often forget that those educational institutions put unusually extensive resources behind those disciplines, as compared with their national peers. Without that commitment, which is far more unusual and is more important to Chicago's economic future and cultural reputation than most people understand, this ascendance would not have taken place.
For much of its early history, of course, the improv and sketch comedy scene in Chicago was, you might say, ragtag, intellectual and lefty. It was seen as something other than the establishment, not a feeder for a big network reliant on appealing to mainstream America. While "Saturday Night Live" scouts have been raiding Second City in Chicago and Toronto as long as there's been "Saturday Night Live," that was not the same kind of ladder into the sort of network job that Colbert just landed. Indeed, "Saturday Night Live" did not represent a rung. It now does. Since Lorne Michaels' NBC show was the only one with long-established connections to Chicago talent, that show's progression further and further into the heart of the cultural mainstream also has been highly significant for Chicago. In fact, it accounts for more than any single factor.
Of course, in the pre-Internet days, it was harder for the word to emerge about breakout talent in some smoke-filled Chicago comedy cabaret. The pioneers — such as Mike Nichols and Elaine May — had, for the most part, to move and start anew. Now, coverage of this scene is widely shared and parsed, on both coasts, for fresh talent. If you now perform on, say, the Second City mainstage, the big guns will, at minimum, be taking a look. You then can slide into something bigger, and there are more things bigger, and then, if you don't self-destruct (some things don't change), take it to the next level. And there are more levels. Plus there's a better chance that you have worked with someone already at one of those levels, or they at least take a parental interest in your roots.
Moreover, the kind of talent that now is sought out for a late-night talk show similarly has changed, greatly to the benefit of the Chicago school. Instead of the old interest in, primarily, stand-up comics or neo-vaudevillians, the writer-performer-satirist now is at the top of the desired heap, as the networks know they must fight back against the growth of the current events/cultural commentary/news parody hybrid associated with Jon Stewart and, of course, Colbert himself. Not to mention the funny videos from the land of social media, a form of bite-size competition that is further changing this landscape.
That new emphasis on writing and fast reactions, as distinct from hosting, telling jokes or performing jokes, has played to the strengths of the Chicago school, which somehow managed both to experiment with form and clean up its act at just the right moment. Actually, that crucial moment was well over a decade ago; it's worth remembering that Colbert is hardly a new discovery. It took time. Rather, Colbert is the logical extensions of groundbreaking, neo-absurdist shows like Second City's "Pinata Full of Bees," coupled with the arrival on North Wells and North Clark streets of good-looking careerists rather than neo-Brechtian improvisors with much facial hair.
Meanwhile, Letterman's de-formalized show was a crucial middle-step in the metamorphosis of the comedy establishment. Letterman's show came replete with those famously meta elements, as when Dave lobbed a cue card at the camera, seemingly shattering its lens and the old-school conventions therewith. The issue for CBS this spring has been how to take Letterman's changes to the next logical step, without seeming either to repudiate or repeat them. Colbert, who is known across America primarily for a single, fictional character, is a very clever choice. It is, as Letterman himself has noted, hard to think of a good second choice. It is even harder to think of one not trained and practiced in the Chicago school.
For anyone who has seen Colbert in Chicago — and he has been back here quite frequently, playing himself — the current national bemusement and confusion over his identity versus his boorish character seem strange. Colbert may be dark, smart and unstinting — and much less sweet than Fallon, thus assuaging the grave danger of un-Lettermaning the Letterman slot — but he is even funnier, and likely a better interviewer, as himself. Simply put, that's just an easier assignment for a man who, in Chicago at least, long has been the consummate kind of entertainer, quick with a savvy nod to Rahm Emanuel at a Lookingglass Theatre gala (Colbert went to school with the Lookingglass crew), but also able to perfectly re-create an old Second City backyard basketball sketch at the troupe's 50th anniversary, an exquisite piece of vintage Colbert funny, dating from back when he and today's late-night TV were being formulated, to the great eventual benefit of both.