Bill Carter: The Allure and Danger of Stephen Colbert Being Himself

This story first appeared in the Sept. 11 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

Stephen Colbert is free at last. Free, that is, to be Stephen Colbert, 51-year-old father of three, husband of 22 years, professional entertainer, soon-to-be signature star of CBS in late-night television — as opposed to Stephen Colbert, dim-bulb host of a faux right wing talk program, persistently, in every act of comedy or on-air conversation, at a distinct remove from his real reality — as it were.

Colbert, who may qualify as the most thoughtful and intellectual figure ever to sit behind a late-night desk and crack Donald Trump hair jokes, has made little secret of the relief he feels at this transition. “Now I don’t have to hold back at all,” Colbert told reporters at the summer press tour. “I had to put everything through, like, an occipital CPU up here to live?render what my character would think about what the person just said but still have my intention behind it. Now I can just talk.”

Just talk. That sounds like a man experiencing liberation. For the past several years, members of Colbert’s team ­— his writers, producers and management — have been aware of the growing strain Colbert was feeling: a brilliant, empathetic performer, maintaining the facade of the raging ignoramus throughout his long tenure on Comedy Central’s The Colbert Report. It was a performance that earned Colbert extraordinary accolades, not merely the Emmy and Peabody Awards the show racked up, but also the awed admiration of fellow comics, who at various times expressed incredulity that a late-night host could essentially perform one sketch for nine years. And make it look easy.

The truth is, it was, at times, excruciatingly hard. “People had no idea how difficult the process was,” one of his team members tells me. “It was the only show where, every night, the jokes would have to be written and then rewritten to fit the character. Stephen was burning out.” Colbert never lost the thread of how his character should act, even though, especially in recent years, the real Stephen broke through on more numerous occasions — notably when the jokes made him sincerely break up.

But Colbert still felt compelled to visit guests before tapings to explain that they should be aware throughout the conversation that his character was a moron. (He told comic David Steinberg on his Showtime show: “I worked hard not to make him an asshole but to make him an idiot, which is a different thing. An asshole is an idiot who thinks not caring if you love him is adorable. Whereas an idiot doesn’t know that what he’s doing is alienating you. He wants you to love him still.”)

On CBS’ ‘Late Show,’ Letterman wore tailored suits and invited mainstream guests.

In saying things this summer like, “I felt I had done everything I could” with the character, Colbert was repeating what staffers had told me years before he accepted the CBS job: He was going to leave The Colbert Report soon, no matter what happened anywhere else.

It certainly is rare for a star to feel compelled to abandon a beloved comic creation. There are some precedents: In a minor key, Bill Dana walked away from his hit character of the 1960s, Jose Jimenez, responding to the sensitivities of the Hispanic community. (He held a mock funeral for the character on Sunset Boulevard.) More prominently, Charlie Chaplin announced he was abandoning his iconic character, The Tramp, when talkies came in. (Chaplin had a British accent he felt would jar audiences who expected the character to be American. He did bring The Tramp back in the two silent comedies he made in the 1930’s, City Lights and Modern Times.)

And retooling a comic approach is not new to late night. In fact, the last time a comic first stepped onto the stage of the Ed Sullivan Theater as host of Late Show, in 1993, he was consciously altering his act to fit a new program. In a meeting with then-NBC chief executive Bob Wright, whom he still hoped to persuade to install him over Jay Leno on The Tonight Show, David Letterman laid out his plan to smooth out the edginess that had marked his 12:30 a.m. show on NBC, promising more mainstream guests, a traditional monologue as well as suits and dress shoes over his then-trademark blazers and sneakers. “I have to change the show, and I am completely able to do that, and I want to do that,” Letterman told Wright at the time.

By contrast, when Conan O’Brien left Late Night in 2009 for Tonight, he resisted the notion his style had to be revised. “I read that it’s time for Conan to grow up because he’s going to 11:30,” O’Brien said on his Late Night finale. “I assure you: That’s just not going to happen. It can’t. This is who I am, for better or worse.”

Fairly or unfairly — and Conan fans continue to enjoy his comic creation on TBS — one member of the Colbert team makes the observation that O’Brien might have suffered when he moved to 11:30 because people might have felt like, “I’ve seen it.”

O’Brien’s ‘Tonight Show’ largely mimicked his ‘Late Night’ schtick.

Whatever Colbert and his writers come up with when they land on CBS on Sept. 8, it is guaranteed to be something Colbert’s fans have not seen before. The star has left no doubt he is all in on the transformation. Colbert has been up for everything CBS’ Leslie Moonves has asked him to do, including more than 160 promotions with individual CBS stations and multiple promo spots for the network to use all over its schedule, from primetime to NFL games. George Schweitzer, the longtime CBS executive in charge of promotion, praises the comic’s eagerness to engage. (In 1993, Letterman devoted exactly one day to shooting CBS promos, recalls Schweitzer.)

The creative aspects of the promotion all were handled by Colbert’s staff. The host personally recruited Mitt Romney for one promo, and approaching a prominent Republican was no accident. The show’s creative team is deeply aware of two things: the need to send a message that the host no longer is sending up extreme conservative ideas; and the opportunity to be the late-night leader in politically charged humor now that Colbert’s mentor, Jon Stewart, has left the scene.

Colbert even was intensely involved with the renovation of the Ed Sullivan Theater. He tells me he loved the effort to restore the building, including the marquee on Broadway, to its 1927 roots. “CBS did an amazing job,” says Colbert, citing the addition of C-O-L-B-E-R-T in massive letters down the front of the building as a nice touch. “Believe me, I don’t host a show without my name out front,” he jokes.

That is, the name Stephen Colbert — of South Carolina, Second City and Montclair, N.J.; the real guy, ready to put a fresh coat of paint on what has been, already, a bright and shining career.

At the same time, he does not want one message to be lost: Different guy, different show, still funny. “The expectation of your going to a different place is, you gotta do a different show,” he says. But, he adds, “That old show got us this gig. Let’s not forget our own level of stupidity that we worked so hard to achieve.”