Contributing to the special’s uncanny vibe was that Colbert was broadcasting from his usual studio, where he hosts The Late Show on CBS, but with the free rein granted by premium cable, he was swearing with aplomb. At first, he reeled off jokes echoing what was obviously an outcome he presumed would happen—the election of Hillary Clinton. “Donald Trump wanted to build a wall, and Hispanics want him to pay for it,” he said, noting increased Latino turnout in states in Florida and Texas.
The actor Jeff Goldblum appeared for a scripted bit mocking his nervy character from Jurassic Park, calling Trump a Republican Party experiment gone wrong. “The GOP took a hardened chunk of anger with prehistoric ideas and created a monster,” he stuttered, to appreciative laughs from the live audience. Then real-time news began to trickle in, with the journalists Mark Halperin and John Heilemann joining Colbert to talk voting numbers and confront him with the reality that Trump was over-performing polls and likely to win states like Wisconsin and Michigan.
Colbert was once a chief clown for the left in his role at The Colbert Report, mocking the exaggerated right-wing punditry of Fox News. At The Late Show, he’s walked a tighter line, making his political feelings clear (he was obviously a Clinton voter) while trying to reach out with empathy to the other side. He’s noted that his whole extended family (from South Carolina) is politically divided, but that they love each other anyway. When he interviewed Trump, he tried to get the candidate to offer conciliatory words, and perhaps even apologize to people he might have offended during the campaign (Trump declined).
When Halperin finally told Colbert that Trump would likely win the election, the host visibly deflated. Comedy is, of course, allowed to be partisan, and it was not a moment where Colbert could disguise his feelings. “This has been the darkest presidential campaign that I’ve covered. I’ve covered every one since 1988, and in the aftermath, I think this is going to be a really challenging time for America. Good line for a comedy show, right?” Halperin said, half-jokingly. “I'm not sure if it’s a comedy show at this point,” Colbert replied, with a quiet grimace. “I think we’re in the middle of a documentary right now.” His words reflected the disbelief of millions who had trusted in public polls and data journalists predicting a victory for Clinton—and who all saw the results suddenly swerve in the opposite direction.
During their conversation, Florida was called for Trump, putting him on the doorstep of 270 electoral votes. “Wow. That’s a horrifying prospect,” Colbert said. “I can’t put a happy face on that, and that’s my job.” It was darkly compelling television, in all its awkwardness—it was live, it was unrehearsed, and it was, for at least a moment, deeply honest. Colbert made sure to note the division between his audience and the voting public. “For Trump supporters, this is porn, what we’re going through right now,” he said with a laugh.