Colbert kicked off his Monday night episode by discussing Trump’s frequent assertions that the upcoming election is “rigged,” an alarming undermining of the country’s democratic norms that has many pundits worried. “It’s not rigged ... but everybody’s angry in the country, everybody’s mad,” O’Reilly said, a catch-all argument that many of his Fox News associates have trotted out to explain Trump’s victory in the Republican primaries. Colbert, to his credit, challenged that assertion, the only real moment of tension in a more than 10-minute conversation.
“Not everybody’s angry,” Colbert said. “Some people are angry, some people are scared, some people are …” “Disenchanted?” O’Reilly offered. “Well, or disgusted,” Colbert replied. “Honest to God, it’s not all the same emotion.” In that moment, Colbert offered a glimpse of the new persona he’s tried to carve out over a year at The Late Show—a sort of arch conscience for America, less sarcastic than his predecessor David Letterman, and less cynical than his former partner Jon Stewart at The Daily Show. But unfortunately it was only a moment of incisiveness that Colbert failed to follow through on.
It’s difficult to define Colbert’s current style as a political comedian. His peers, meanwhile, have found their lanes: Seth Meyers is analytical and precise at Late Night, Samantha Bee is righteously furious on Full Frontal, John Oliver is an impassioned activist at Last Week Tonight. All of those approaches owe a debt to The Daily Show, where Colbert’s character first debuted, and arguably to Colbert himself. It’s undeniable that The Colbert Report is one of the most influential comedy programs of all time. It should have been a short-lived high-concept lark—instead it became a 10-year parody of talking-head cable news that often made its points more skillfully, and dug deeper with guests, than many of the shows it mocked. Colbert’s appearance on The O’Reilly Factor came a few months after his legendary performance at the White House Correspondent’s Dinner in 2006. Both were merciless performances, holding a funhouse mirror up to mainstream conservatism with “Colbert” and delighting in the puzzled response.
On The Late Show, Colbert has lacked that kind of single-mindedness. As a result, he’s been stranded in a middle ground, wanting for the viral presence of rivals like Jimmy Fallon or James Corden, while also being not nearly as hard-hitting on politics as Bee, Meyers, or Oliver. In his early weeks, he had some dazzling interviews, including an emotional conversation with Vice President Biden after Biden’s son Beau had just died of cancer. At other times Colbert’s interview style has been strangely flat—his awkward interrogation of Trump saw him try to go the empathetic route, giving the candidate a chance to apologize, and then floundering when Trump refused. The show has undergone changes behind the scenes, with a new showrunner coming in to try and hone a stronger personality for the show, but it hasn’t quite worked: Standout moments have included Colbert bringing his old persona back, or calling Stewart in for a guest spot.