Five months and five episodes into his Netflix interview show My Next Guest Needs No Introduction, David Letterman finally welcomed a fellow comedian onto his stage.
Newly crowned Tony Award nominee Tina Fey joined Letterman for a discussion about her career in comedy, from starting out in the Chicago improv scene to becoming the first female head writer of Saturday Night Live, to writing her best-selling memoir Bossypants and her hit Broadway adaptation of Mean Girls.
Letterman and Fey began by comparing notes on how to keep their kids from sinking too deeply into technology and what it’s like to grow up with a “hard-ass” father. Fey got uncharacteristically emotional when she told Letterman about getting the Mark Twain Prize for American Humor in 2010.
“They wanted to give it to me after Sarah Palin,” she said. “I played Sarah Palin and they were like, ‘We want to give you a prize.’” Fey remembered talking to Lorne Michaels, who had previously received the same award for his decades producing Saturday Night Live. “Lorne, very wisely, said, ‘Take it while your parents are alive.’” Her father passed away just a few years later.
When Letterman suggested that Fey’s impression of Palin “moved the needle” in the 2008 election, she said, “I don’t think it did. But now it seems like such a folksy, simpler time, doesn’t it? That election was so civilized, comparatively.”
Fey said that she and Seth Meyers and Amy Poehler, who all collaborated on those sketches, were “so careful” not to write anything into them that didn’t “believe in.” They weren’t writing the sketches to “convince” anyone of anything, but rather to “observe the truth and say it.”
After just six weeks of playing the vice presidential candidate on SNL, the real Sarah Palin was invited to appear side-by-side with Fey on the show. Fey went to Lorne Michaels and said, “‘Please, I don’t want to do it with her.’ Because I just didn’t feel right about it. And I was like, if I do it, that’s what they’re going to show at the Emmys when I die.”
Ultimately, instead of acting with Fey in the sketch, Palin appeared backstage with Lorne Michaels, watching Fey and Poehler perform on a TV screen. During the sketch, Alec Baldwin entered the scene and initially “mistook” Palin for Fey before adding, “You are way hotter in person.”
“We met and she was perfectly nice,” Fey told Letterman, but said it was also weird. “Do you ever feel like, ‘I shouldn’t be this close to the people running the world?’” she asked him. “Yes,” he replied.
“Could you get me on that show?” Letterman asked of SNL at one point. “I don’t want to do anything, because I understand the hours are rigorous.” Really, he said, he just wants to be a background actor.
“100 percent,” Fey said. “I’ll call and make it happen.”
More seriously, Letterman said that “years and years and years ago” Lorne Michaels asked him to host the show but he decided not to do it. “I was scared silly,” he said.
“When I had a television show, people would always say to me, ‘Well, why don’t you have women writers,’” Letterman recalled later. “And the best I could come up was, ‘I don’t know.’ I didn’t know why there weren’t women writers. There was no policy against women writers. And I always thought, well jeez, if I was a woman I’m not sure if I would want to write on my little nickel-and-dime, dog-and-pony show anyway, because we were on at 12:30.”
“Yeah, we do want to write on it, though,” Fey said, getting a huge cheer from the live audience.
Letterman admitted to his “ignorance,” saying, “I feel bad for that.”
“I’m relieved I don’t work at SNL [right now],” Fey said later. “The level of outrage is so high. It feels like talking to anyone, anywhere in 2018 is just landmine hopscotch.”
One of the last times she appeared on the show was just after the white-supremacist rally in Charlottesville. She was hesitant, but ended up appearing on “Weekend Update” and spoke out as a University of Virginia alum about the dangers of Nazism. It was a very funny piece that also received some major backlash for urging people to eat cake in response.
Letterman said he thought the bit was “perfect,” but Fey replied, “Turns out it was not, sir.”
“I’m well aware that there were some differing views,” Letterman said. “But I just thought, here’s something to let the gas out of a situation that should not have happened. And I thought it was performed beautifully and written beautifully.”
Fey thanked Letterman for the “kind” words, before adding, “Here’s what was wrong with it.”
She said she was trying to “provide some relief” for viewers after the violence that had occurred just a few days earlier. “You try your best, you try to have your eyes open, you try to be so mindful,” she said. “But it’s also a fast-moving train. So I felt like a gymnast who did a very solid routine and broke her ankle on the landing.” She said she felt like it was in the last two or three sentences of the piece that she really “screwed up.”
Fey ended that piece by encouraging “all good, sane Americans” to treat the upcoming alt-right rallies “like the opening of a thoughtful movie with two female leads: Don’t show up. Let these morons scream into the empty air.”
“The implication is that I was telling people to give up and not be active and to not fight,” she told Letterman. “That was not my intention, obviously.” Though Fey is not on social media herself, she said she knew something had gone wrong when she started getting texts from friends that read, “I don’t care what anybody says.”
If she had a time machine, Fey said she would go back and end the piece by saying, “Fight them in every way except the way that they want.” She considered making a Twitter account just to apologize, but wisely realized that would probably make things even worse.
“The culture of apology is not for me,” she said. “So what I will do is I promise, I swear to God anybody who was mad at me, I hear you and I will learn, but I’m also not going to stop trying.” She will have another chance when she hosts the show’s season finale on May 19.
Toward the end of the episode, Fey shared one more SNL story with Letterman about the first time Donald Trump hosted the show in 2004. Fey was anchoring “Weekend Update” at the time and decided to do a bit where they renamed the segment “Weekend Trump-date.”
When Trump walked in and saw her in the overly sexualized beauty pageant costume she had on for the sketch, he said, “You look very nice like that, you should dress like that more often.”
Fey said this is the “disconnect” with Trump. He had “imagined that someone has asked him what he thinks about something” when they had not.