Stephen Colbert Didn't Want to Write Jokes About Trump Win for Showtime Special

Stephen Colbert at Montclair Film Festival Benefit With John Oliver - H Getty 2016
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The 'Late Show' host joined fellow 'Daily Show' alum John Oliver for a nearly two-hour discussion that, among other topics, explored the fear of what could happen when Donald Trump becomes president.

Stephen Colbert and John Oliver continued to tackle the potentially frightening prospect of Donald Trump becoming president at a benefit for the Montclair Film Festival on Saturday night.

Introducing the two Daily Show alums' conversation, titled "Wow, That Was Weird," Colbert and Montclair Film Festival executive director Tom Hall admitted they didn't expect to be facing the current political landscape when they came up with that title.

"When we planned this evening, I think we all thought we'd be looking back with laughter instead of looking forward with deep concern about the uncertainty we face," Hall said at the top of the show, which lasted nearly two hours, including an extended audience Q&A.

When Colbert took the stage next, one of his first remarks to the audience was, "Boy, I did not plan this well, which gives me something in common with half of the nation."

After a mournful chuckle, he continued, "We called this evening 'Wow, That Was Weird, A Conversation With Stephen Colbert and John Oliver.' I did not know we should've called it, 'Wow, This Continues to Be Weird.'"

The fundraiser for the Montclair Film Festival, which Colbert, whose wife is a member of the board, has long supported, wasn't the only election-related event that didn't turn out the way the talk show host planned, or at least not one of the ways he planned.

At the end of the event, when asked about completed pieces they had to kill, Colbert offered some further insight into what he and his team had planned for their live election night special on Showtime. While Late Show showrunner Chris Licht said before the special that they'd prepared a few different shows, depending on what happened, Colbert suggested on Saturday night that he didn't prepare as much comedic material for one scenario — the one that ended up playing out from 11 p.m. to 12 a.m. ET on Nov. 8.

"There was not a bear big enough in the world that we weren't loaded for. We were so loaded for every possible eventuality," Colbert explained. "We had so many guests. We had so many pre-taped pieces, all based on a different eventuality. We had three shows: Hillary Clinton wins and we know; Hillary Clinton wins and we don’t know, because it’s not called before the show’s over; Donald Trump's going to win and we don’t know, because everyone said he had such a narrow path to victory. That's not wishful thinking, that's what everyone was saying. And then there was the last show, which is the show we did, which is Donald Trump is going to win and we know he's going to win. My execs and my writers were like, 'You don't want to write something for that?' and I'm like, 'No! There is nothing you can write. You don't understand. I have 400 people in my theater. If we know Donald Trump is going to win, it's going to be like doing stand-up comedy for one of those Chilean soccer stadiums where the villagers watch you execute one of the natives. There will be no laughter!' We only did about 20 minutes of material before we went, 'F— it, it's going to be him, let's just talk for another hour.' So I think we have two and a half whole shows that you will never see of material that we had to kill that night."

Colbert added that the special was "the hardest thing I've ever done in my life," and joked he would have preferred a terrible gig like the one Oliver described earlier in the evening, in which he performed for an audience of four people, who slowly walked out until the last person, a woman, left him alone onstage.

Oliver wasn't on Colbert's Showtime special, but he said he could sympathize with Colbert's predicament and got a glimpse of his show. Oliver said he was home at 10:30 and thought, "Oh shit, Stephen has a show in half an hour. I'm glad I'm not him right now."

The Last Week Tonight host explained that he turned on Showtime "at 11:02 and saw [Colbert's] eyes," and quickly turned off the special.

Colbert added, "I was tying my tie at 10:30 and I went, 'Oh, he took Ohio. Oh, well, we expected that. He took it by 11 points. Wow! That's not expected.' And then over my guests' shoulders, people kept holding up signs that said, 'Florida, Iowa, Nebraska.'"

And he said that while his team had prepared a number of fake commercials, "none of them were appropriate once we knew we were playing to an audience of the condemned. Our audience was sobbing openly. And those are people who work for me, like my cameramen."

Colbert employed a bit of nudity at the top of the show but the host, who had teased that he would take advantage of the lack of censorship on the premium cable channel, said he had a more elaborate use of nudity planned if Hillary Clinton had won.

"We hired a series of very fit naked men, with high, tight butts. We were going to bring them out if Hillary won," Colbert explained. "And painted on their asses was going to be [one letter on each behind] 'I'm with her.' And then very early on [in] the evening, we were like, ‘You can let those guys go.'"

During his Showtime special, Colbert did offer a series of reassuring remarks for his troubled audience, and at the top of Saturday night's show he said, "It's a great country and it will continue to be so as we go forward."

But as the evening went on, Colbert indicated that he was genuinely afraid of what could happen when Trump becomes president.

"I’m all for giving him a chance, but don’t give him an inch," he said. "Because I believed everything he said, and I remember everything he said. And it’s horrifying. It's possible. The job changes a man. That's the cliche of the presidency."

Added Oliver, "Sure. It has. We don't know how this is going to play out. I don’t know if there is too much concrete evidence to be too comfortable, going forward."

Colbert then explained why he feared "we're most screwed": "Every president tries to achieve what they promised and you can say, 'Well, there are levers of power in Washington that can slow him down.' But two things: One is they're cowards. Second is that the levers in Washington are apparently merely attached to blinking red lights that make the people happy when they pull. Because they tried to stop Trump. Everybody tried to stop Trump, do not delude yourself. Everyone except the people he's going to appoint tried to stop him and they didn't. He owes them nothing. He goes out on the balcony and he says to the crowd, 'Shall I do it?' And they say, 'Yes.' And he says, 'It shall be so.' And the balcony is Twitter. He goes onto Twitter and he goes, 'What do you think? Do you think I'm right?' That's what scares me, that he owes the checks and balances of Washington nothing because they tried to stop him and they couldn't. And he's a vindictive person. So it's all going to be fine. Merry Christmas."

Colbert also doesn't find joy in the idea of writing jokes about a Trump presidency.

"The next person who says to me, 'You must be happy on a certain level,' is going to have their eye carved out," the Late Show host said.

And he's not happy with the term "fake news" being used to describe the inaccurate stories that may have helped Trump's campaign or hurt Clinton's campaign. Colbert pointed out that "fake news" was what they did at Comedy Central's The Daily Show, in that half of the joke was that they were delivering jokes in a news format.

"The fact that they call this stuff 'fake news' upsets me because this is just lying,” he said.

But Colbert said he did prepare his staff for the fact that his audience's mood is changing.

"Look, I've been through this a few times before, first with Jon [Stewart] and then my own show," he said he told his staff. "And there comes a moment when there's sort of an emotional transformation that goes on, and you have to be aware of it when it happens so you understand what the audience's appetite is. But then you're the chef. You don't make necessarily the meal that they request but is something that you think is worth talking about and jokes you want to make. But you have to understand that there is a transformation going on in the emotional state of the audience."

Both Colbert and Oliver instructed people concerned about a Trump presidency to vote on the local level, where, as Oliver put it, "shit actually goes down."

And Colbert encouraged people to find common ground with one another, not necessarily based on politics.

"Get involved in local organizations — whether they be charitable organizations, arts organizations — and get to know your neighbors," he said. "There's something to the idea that there are two separate Americas living in different bubbles, but there are reasons to get together that have nothing to do with politics. If there are people here who voted for Trump, God bless you for supporting the Montclair Film Festival. There have to be moments in our lives that are not centered around politics and things that we do that are not competitions, and politics is jockeying for power. So get involved in your local community in significant ways that lets you meet your neighbors.”

It wasn't all doom and gloom. Colbert and Oliver kept it light when not talking about Trump, and Oliver attempted a bit of dark humor when Colbert asked if he was worried he'd be sent back to the U.K., given how he's criticized the president-elect on his show.

Colbert asked, "Are you peering out the windows?”

Oliver answered, “No, but one day, like Jurassic Park, maybe I’ll see the water shifting and go, ‘Here they come.’”

The two even kicked things off on a silly note, with the stage decorated in a way befitting their backgrounds, with a U.S. flag pillow and mug on Colbert's side and a Union Jack flag pillow and mug on Oliver's side. After taking their seats, both Colbert and Oliver removed the pillows and engaged in a short pillow fight, jokingly shouting, "No, your country's stupider!"