Why Stephen Colbert isn't connecting

Almost 10 years ago, Stephen Colbert appeared on Fox News’ The O’Reilly Factor in character as the Colbert Report host—a pugnacious, egotistical super-pundit who tolerates no criticism. Colbert has frequently acknowledged that O’Reilly was the chief inspiration for his on-screen persona, and it was hilarious to see the imitation go up against the real thing. “What I do, Bill, is I catch the world in the headlights of my justice,” Colbert bragged to a smirking O’Reilly. “I’m not afraid of anything. Well, I might be afraid of you.” The same day, O’Reilly went on Colbert’s show; the combative tension between the two remains genuinely thrilling to watch.

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On Monday night O’Reilly went on The Late Show With Stephen Colbert to talk about the state of the Republican Party and Fox News. The conversation was civil, at times energetic, but mostly bland. O’Reilly, clearly far more at ease, pontificated on the state of the Trump campaign while dodging any discussion of some of its biggest controversies. Ultimately, it was a notable reminder of just how much things have changed for Colbert since he cast off his late-night character and joined CBS. To stand out in a crowded landscape, Colbert has pursued even-handedness and empathy, a drastic swerve away from his former public persona. It’s an approach both noble and misguided, but a year into his Late Show run, it’s kept him firmly out of the zeitgeist.

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